Daniel v. Hawkins ( 2023 )


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  •            IN THE SUPREME COURT OF THE STATE OF DELAWARE
    BRADLEY DANIEL, an individual, and §
    MEDAPPROACH HOLDINGS, INC., a §
    Delaware corporation,              §
    §          No. 184, 2022
    Defendants Below,           §
    Appellants,                 §
    §          Court Below: Court of Chancery
    v.                          §          of the State of Delaware
    §
    SHARON HAWKINS, individually and §
    derivatively on behalf of          §          C.A. No. 2021-0453
    MEDAPPROACH, L.P.,                 §
    §
    Plaintiff Below,            §
    Appellee.                   §
    Submitted: November 2, 2022
    Decided: January 6, 2023
    Before VALIHURA, VAUGHN, and TRAYNOR, Justices.
    Upon appeal from the Court of Chancery. AFFIRMED.
    David Teklits, Esquire (argued), Sara Barry, Esquire, Morris, Nichols, Arsht & Tunnell
    LLP, Wilmington, Delaware; Of Counsel: Jeffrey Alan Simes, Esquire, Goodwin Proctor
    LLP, New York, New York for Appellants.
    Richard I.G. Jones, Esquire (argued), John G. Harris, Esquire, Berger Harris LLP,
    Wilmington, Delaware for Appellee.
    VALIHURA, Justice:
    Following a trial, on April 4, 2022, the Court of Chancery entered judgment in favor
    of appellee Sharon Hawkins (“Mrs. Hawkins” or “Appellee”) on her request for a
    declaration that the irrevocable proxy which provides appellant W. Bradley Daniel
    (“Daniel”)1 with voting power over all 100 shares of N.D. Management, Inc. (“Danco GP”)
    (the “Irrevocable Proxy”), does not bind a subsequent owner of such Danco GP shares.
    The Court of Chancery also held that an addendum to the Irrevocable Proxy does not
    obligate the current owner of the Danco GP shares, MedApproach, L.P. (the “Partnership”),
    to demand that the buyer in a sale to an unaffiliated third party bind itself to the Irrevocable
    Proxy.
    The Irrevocable Proxy was executed on February 5, 1997 by the then-owner of all
    100 shares of issued and outstanding stock of Danco GP. It granted three individuals,
    including Daniel, the power to vote the Proxy Shares (defined below). On January 1, 1999,
    as part of an internal restructuring in which the Partnership was created and acquired 75%
    of the Proxy Shares, the Partnership executed an Agreement To Be Bound By Irrevocable
    Proxy and Power Of Attorney, binding itself to the Irrevocable Proxy.2
    The Partnership dissolved on February 28, 2021, and is now in the process of
    winding up. As its principal asset, it owns 75% of the issued and outstanding stock of
    Danco GP (the “Majority Shares”). Appellee currently owns 88% of the Partnership and
    1
    MedApproach Holdings, Inc., referred to herein as “Holdings” is also named as a defendant.
    Daniel owns 100% of Holdings.
    2
    App. to Opening Br. at A370 (Agreement To Be Bound By Irrevocable Proxy and Power of
    Attorney).
    2
    desires to purchase the Majority Shares in the winding up process. But for the Irrevocable
    Proxy, the owner of the Majority Shares would control both Danco GP and the entity
    managed by Danco GP, Danco LP (defined below).
    Daniel appeals the Court of Chancery’s judgment that the Irrevocable Proxy does
    not run with the Majority Shares.3 He argues that the Court of Chancery committed the
    following legal errors: (1) first, rather than interpret and apply the plain language of the
    Irrevocable Proxy as written, the Court of Chancery erred in relying on the Restatement
    (Third) of Agency, which was not adopted until nearly a decade after the parties entered
    into the Irrevocable Proxy, (2) second, it read additional language into the Irrevocable
    Proxy in order to support its finding that the broad “catch-all” language that the parties
    included to prevent termination of the Irrevocable Proxy did not encompass a sale of the
    shares, and (3) third, it did not give effect to all of the terms of the Irrevocable Proxy and
    it improperly limited the assignment clause of the Irrevocable Proxy so as not to bind
    assigns of the stockholder.
    For the reasons set forth below, we AFFIRM the judgment of the Court of
    Chancery.
    3
    Daniel does not challenge the Court of Chancery’s conclusion that the Addendum does not
    obligate the Partnership to demand that the buyer in a sale to an unaffiliated third party bind itself
    to the Irrevocable Proxy.
    3
    I.   FACTUAL AND PROCEDURAL BACKGROUND4
    A. The Founding of the Project
    Population Council, Inc. (“Popco”) is an international not-for-profit corporation
    focused on family planning. In 1994, a French pharmaceutical company granted Popco a
    license to manufacture, market, and distribute the oral abortion drug RU-486, more
    commonly known as mifepristone. Once granted the license, Popco began a search for an
    investor to manufacture and distribute the drug for domestic and international use (the
    “Project”). In what would turn out to be an unfortunate choice, Popco selected Joseph D.
    Pike (“Pike”), who it had previously worked with on similar ventures, to undertake the
    Project.
    Pike formed a complex entity structure to consummate the venture, placing himself
    at the helm. He formed Danco Laboratories, Inc., a Cayman Islands company (“Danco
    Labs”) as the main operating entity. Danco Labs subsequently domesticated into a
    Delaware limited liability company and is now known as Danco Laboratories, LLC.
    Through an affiliate, Popco granted an exclusive sublicense to Danco Labs to implement
    the Project in the United States.5 Ultimately, the outcome of this litigation will determine
    the control arrangement of Danco Labs.
    Pike then formed Neogen Investors L.P., a California limited partnership. Neogen
    Investors L.P. is now known as Danco Investors Group, L.P. (“Danco LP”). Danco LP
    4
    Unless otherwise noted, facts are taken from the Court of Chancery’s memorandum opinion. See
    Hawkins v. Daniel (Chancery Opinion), 
    273 A.3d 792
     (Del. Ch. 2022).
    5
    App. to Opening Br. at A132 (Offering Memorandum at 1).
    4
    owns 100% of Danco Labs and was formed as a holding company to raise equity financing
    for the Project. Pike’s goal was to solicit investors to invest in Danco Labs by purchasing
    limited partnership interests in Danco LP.
    Lastly, Pike formed N.D. Management, Inc., a Cayman Islands company (“Danco
    GP”) as Danco LP’s general partner. Danco GP has since domesticated into a Delaware
    corporation. Initially, Pike owned 100% of Danco GP, which consists of 100 shares of
    issued and outstanding stock. Because Danco GP controlled Danco LP as its general
    partner, and Danco LP owns 100% of Danco Labs, Pike effectively controlled Danco Labs
    through his 100% ownership of Danco GP. The same remains true today: whoever
    controls Danco GP controls Danco Labs and the Project.
    Pike then began raising money for the Project by selling limited partnership interests
    in Danco LP. From about November 1995 to February 1997, Pike raised approximately
    $13.35 million.6 One of Pike’s primary investors was appellant Daniel. Daniel invested
    in Danco LP through his newly formed entity MedApproach L.P., a Tennessee limited
    partnership (“Old MedApproach”), which he caused to purchase limited partnership
    interests in Danco LP. At the time, Daniel owned Old MedApproach through its general
    partner, Bio-Pharm Investments, Inc., a Tennessee corporation. Bio-Pharm Investments,
    Inc. has since become defendant below-appellant Med Approach Holdings, Inc., a
    Delaware corporation (“Holdings”). Daniel owns 100% of Holdings. In 1999, Old
    6
    
    Id.
     at A135 (Offering Memorandum at 4).
    5
    MedApproach was restructured and divided into three separate entities, one of which is the
    Partnership.
    Around this time, Daniel was introduced to Mrs. Hawkins’ husband, Gregory
    Hawkins (“Mr. Hawkins”) through a family connection who suggested that the two discuss
    the Project. After discussing the opportunity with Daniel, Mr. Hawkins decided to invest.
    Instead of purchasing limited partnership interests directly in Danco LP, Mr. Hawkins
    invested by purchasing limited partnership interests in Daniel’s entity, Old MedApproach.
    Old MedApproach then used the money invested by Mr. Hawkins to purchase limited
    partnership interests in Danco LP. After investing $1.5 million, Mr. Hawkins owned
    approximately 75% of the limited partnership interests in Old MedApproach. Three years
    later, Mr. Hawkins transferred his interest in Old MedApproach to his wife, appellee here,
    due to personal financial difficulties. As between Mr. Hawkins and Mrs. Hawkins, Mr.
    Hawkins was substantively involved in the Project at the relevant time period and, as such,
    gave the substantive testimony before the Court of Chancery.
    B. The Downfall of Joe Pike
    In May 1996, Pike pled guilty to misdemeanor forgery charges in North Carolina
    arising out of a 1985 transaction. He was disbarred from practicing law in the State of
    North Carolina and faced criminal penalties. Pike’s legal trouble was news to Popco. Pike
    had failed to disclose any legal difficulties or the underlying events to both Popco and
    investors in Danco LP. Further, Popco believed that Pike had misled investors about
    potential uses of their investment and the payment of fees, and various other aspects of the
    Project. To avoid jeopardizing the Project, Popco sought to extract Pike from the Project
    6
    as quickly as possible. In November 1996, Popco filed a complaint in New York state
    court requesting that the court remove Pike from his leadership roles and rescind his
    interest in the Project.7 It also threatened to cancel the sublicense it had granted to Danco
    Labs. On December 11, 1996, in the face of this existential threat, Pike, Project investors,
    and Popco met to determine if there was a path forward.
    Pike, Popco, and the investors in Danco LP were all represented at the meeting. The
    Project investors were represented by five individuals selected from among their ranks:
    Daniel, Brian Freeman, Jeff Rush, Richard Cusac, and William Elkus (the “LP
    Representatives”). As representatives, they would present any agreement reached with
    Pike and Popco to the remaining investors for their review and approval. 8
    Freeman and Rush owned limited partner interests directly in Danco LP. They also
    had solicited additional investors for the Project and served as advisors to Pike. Cusac and
    Elkus owned limited partner interests directly in Danco LP as well, but the record is limited
    as to any further involvement they may have had in the Project.9
    Daniel represented Old MedApproach at the meeting. Having chosen not to attend
    the meeting due to the political climate and controversy surrounding mifepristone, Mr.
    Hawkins relied on Daniel for news of the negotiations with Pike and Popco. Daniel
    communicated regularly with Mr. Hawkins, sought his input, and kept him apprised of
    developments.
    7
    
    Id.
     at A205 (Offering Memorandum at 75).
    8
    Chancery Opinion, 273 A.3d at 799.
    9
    Id.
    7
    At the negotiating table, Popco put forth two demands. First, Popco reiterated the
    demand it made in its November suit: It wanted to expel Pike from any control or
    management of the Project. Because Pike held his interest in Danco LP through Danco
    GP, this would mean, among other things, Pike would have to sell at least a majority of his
    100 shares of Danco GP and relinquish the voting rights to all 100 shares. Second, Popco
    wanted to ensure that existing Danco LP investors would have the opportunity to rescind
    their investment. Popco feared that the failure to disclose Pike’s legal trouble to investors
    and certain actions taken by Pike constituted a violation of federal and state securities laws
    and wanted to cure a potential violation through a rescission offer.10
    C. The Settlement Agreement
    By the end of January 1997, the LP Representatives reached an agreement with
    Popco and Pike that would achieve Popco’s goals and allow the Project to move forward.
    The terms of the deal were memorialized in an agreement entitled Agreement Regarding
    Neogen Project, dated January 21, 1997 (the “Settlement Agreement”).
    Answering Popco’s first demand, Pike agreed to resign from all of his roles in the
    Project, to sell 75% of his equity interest in the Project, and to give up the voting rights
    allied with the 25% equity interest he was allowed to retain. In other words, Pike had to
    sell the Majority Shares, and, although he could keep the economic rights to the 25
    remaining shares (the “Pike Shares”), he had to give up their attendant voting rights.
    10
    See App. to Opening Br. at A136, A156–57 (Offering Memorandum at 5, 25–26).
    8
    The Settlement Agreement provided that, in return for exiting from the Project,
    selling the Majority Shares, and giving up voting rights to the Pike Shares, Pike was
    contractually entitled to payment of 50% of the distributions on the Majority Shares, up to
    a cap of $21.875 million.11 As an advance on the distributions, Pike received an upfront
    loan in the amount of $3.5 million (the “Pike Loan”), which Pike would repay from the
    first $3.5 million of the distributions.12 Pike also received a consulting agreement that
    would pay him $300,000 per year for five years.13
    Pike’s side of the exchange presented timing issues for the deal. Pike’s sale of the
    Majority Shares was contingent on both the payment of the Pike Loan and the approval of
    the Settlement Agreement.14 Once the Pike Loan was funded, Pike would resign all of his
    positions at any entity associated with the Project and transfer 49.9% of his shares in Danco
    GP.15 Once Popco and the limited partners holding a majority of the interests in Danco LP
    approved the Settlement Agreement, Pike would transfer another 25.1% of his shares in
    Danco GP.16 But Popco wanted Pike to transfer control of the Project as soon as possible
    so that it could cure the potential securities fraud violations and move forward with the
    Project. To solve this issue, Pike agreed to transfer voting power over all 100 of his Danco
    11
    Id. at A021–22 (Settlement Agreement § IV(B)(1)(b)).
    12
    Id. at A018–21 (Settlement Agreement §§ III(A), IV(B)(1)(a)).
    13
    Id. at A021–22 (Settlement Agreement § IV(B)(2)(a)).
    14
    Chancery Opinion, 273 A.3d at 800.
    15
    App. to Opening Br. at A018–21 (Settlement Agreement §§ IV(A)(1)(a)(i), IV(A)(3)).
    16
    Id. at A019 (Settlement Agreement § IV(A)(1)(a)(ii)).
    9
    GP shares as soon as he received the Pike Loan.17 The vehicle for the immediate transfer
    of voting power was the Irrevocable Proxy.           Through the Irrevocable Proxy, Pike
    irrevocably appointed Daniel, Freeman, and Rush (the “Holders”) as his proxies to vote all
    100 shares (the “Proxy Shares”).
    The Settlement Agreement also addressed Popco’s second demand that the investors
    Pike had brought in be offered an opportunity to rescind their interests (the “Recission
    Offer”). The Recission Offer would be presented at the same time as an option for the
    limited partners of Danco LP to invest additional funds in the Project (the “Offering”).
    The terms of the Settlement Agreement created the need for capital to fund the Pike
    Loan and the Recission Offer. The Settlement Agreement contemplated that certain
    “Participating Investors” would provide the funds.18 It defined Participating Investors as
    Old MedApproach, Rush, Freeman, Cusac, and Elkus, plus any other limited partners in
    Danco LP who agreed to sign on to the Settlement Agreement on or before January 31,
    1997. Each Participating Investor would agree to fund an amount of the Pike Loan and of
    the Recission Offer in proportion to their relative interest in Danco LP. In exchange, they
    would receive their pro rata interest in the Majority Shares.
    Finally, the Settlement Agreement contemplated that in the future, the Participating
    Investors could restructure the entities comprising the Project through the creation of a
    17
    Chancery Opinion, 273 A.3d at 813 (finding that the Settlement Agreement “contemplated a
    complex series of transactions that would take time to implement,” and that “[t]he solution was
    the Irrevocable Proxy, under which Pike immediately gave up his voting power over the Proxy
    Shares”).
    18
    App. to Opening Br. at A022–23 (Settlement Agreement § IV(D)).
    10
    “Newco.”19 It provided that the rights covered by the Irrevocable Proxy would inure to the
    interests in the Newco, which would be held by the Participating Investors.20 The provision
    would allow the Participating Investors to replace the entity structure that Pike had created
    to give himself sole control over the Project with a conventional corporate governance
    structure once Pike was out of the picture.
    D. The Solicitation of the Limited Partners’ Approval of the Settlement Agreement
    By its terms, the Settlement Agreement had to be approved by both Popco and a
    majority of the interests in Danco LP on or before February 5, 1997, and would only
    become effective upon such approval.21 The Settlement Agreement also provided that the
    limited partners of Danco LP would have the opportunity to become Participating Investors
    if they joined the Settlement Agreement before January 31, 1997. This imposed on the LP
    Representatives a tight timeline to solicit the consent of the limited partners of Danco LP
    to the Settlement Agreement and to offer them the opportunity to become Participating
    Investors.
    The LP Representatives circulated a short memorandum, dated January 24, 1997, to
    the limited partners of Danco LP that described the Settlement Agreement and the offer to
    become Participating Investors (“the Settlement Memorandum”).22 It asked the limited
    19
    See id. at A019–20, A022–23 (Settlement Agreement §§ IV(A)(2), IV(D)).
    20
    Id. at A020 (Settlement Agreement § IV(A)(3)).
    21
    Id. at A018 (Settlement Agreement § III(A)).
    22
    Id. at A025 (Settlement Memorandum).
    11
    partners to sign and return a form by January 31, 1997 indicating whether they consented
    to the Settlement Agreement and whether they wanted to become Participating Investors.
    The Settlement Memorandum briefly described the negotiations between the parties
    and the opportunity to become Participating Investors. It also informed the limited partners
    of Danco LP of the obligations they would incur under the Settlement Agreement if they
    chose to become Participating Investors. In addition to funding the Pike Loan, they would,
    on a pro rata basis, “provide to [Danco LP] up to $14 million additional capital
    contributions to ‘top up’ the capital of [Danco LP] to the $27.5 million level” originally
    contemplated by the Project documents.23           Limited partners who chose to become
    Participating Investors would be informed of their proportional amount of the Pike Loan
    five days later, on February 5, 1997. They would be informed of their proportional share
    of the additional $14 million capital at an unspecified later date.24
    E. The Revised Settlement Agreement and the Addendum
    Between January 24 and January 31, 1997, the LP Representatives determined that
    giving the opportunity to purchase Pike’s equity interests to all limited partners of Danco
    LP posed logistical and timing issues. Fearing that an extension of the timeline set by the
    Settlement Agreement would delay the deal, the LP Representatives entered into a revised
    settlement agreement (the “Revised Settlement”) which provided, among other things, that
    only Old MedApproach would purchase the Majority Shares from Pike. None of the other
    23
    Id. at A026 (Settlement Memorandum).
    24
    Id. at A028 (Settlement Memorandum).
    12
    limited partners in Danco LP would become Participating Investors. The only Participating
    Investors, and the only counterparties to the Settlement Agreement, would be Old
    MedApproach, Freeman, and Rush. They entered into a letter agreement, dated February
    4, 1997,25 in which they agreed to an allocation of the funding commitment: Freeman and
    Rush each agreed to fund 25%, Old MedApproach agreed to fund the remaining 50%, and
    Mr. Hawkins agreed to backstop the liability of Old MedApproach.26
    The Revised Settlement posed a problem for the Irrevocable Proxy. The Court of
    Chancery found that the purpose of the Irrevocable Proxy was to provide a temporary
    governance regime until Pike was expelled from the Project and a more conventional
    governance structure would be put in place, wherein shareholders would elect a board of
    directors to manage operations.27 Through the Irrevocable Proxy, Pike was appointing
    Daniel, Rush, and Freeman as his proxy to vote the Majority Shares in his capacity as
    owner of the Majority Shares. But the Revised Settlement contemplated that Pike would
    turn over the Majority Shares to Old MedApproach alone, and not the existing limited
    partners of Danco LP who had chosen to become Participating Investors.28 Popco wanted
    to make sure that Old MedApproach would be bound by the Irrevocable Proxy until the
    anticipated reorganization was complete. 29 To address the concern that the Irrevocable
    25
    Id. at A030 (Financial Commitments in Respect of Neogen Project).
    26
    Chancery Opinion, 273 A.3d at 802.
    27
    Id. at 801; see also App. to Opening Br. at A519 (G. Hawkins Trial Testimony at 38).
    28
    Chancery Opinion, 273 A.3d at 801.
    29
    Daniel does not directly assert that the Court of Chancery’s finding that the Irrevocable Proxy
    structure was not intended to be permanent was clearly erroneous. Id. at 804, 813, 818, 833–34,
    835. Instead, he makes a number of assertions that, in our view, either merely state his contrary
    13
    Proxy would terminate when Old MedApproach bought the shares, Popco’s counsel
    prepared an addendum to the Irrevocable Proxy that would explicitly bind Old
    MedApproach as the new owner of the Majority Shares (the “Addendum”). 30                        The
    Addendum is appended to the Irrevocable Proxy and was executed on February 5, 1997,
    the same day as the Irrevocable Proxy.31 In it, Old MedApproach agreed to be bound by
    the Irrevocable Proxy at any time that it is a beneficial or record holder of any of the Proxy
    Shares and agreed not to transfer any such shares of Danco GP to any “MedApproach
    Person,” unless such person agrees to be bound by the Irrevocable Proxy. MedApproach
    Person is defined as Old MedApproach, “or its affiliates, owners, designees, or nominees
    (or their respective successors or assigns).”32
    view, or fail to demonstrate any error, let alone clear error, by the trial court. See, e.g., Opening
    Br. at 13. These assertions rely in part on extrinsic evidence. However, the trial court found that
    the extrinsic evidence cut both ways. We respect the Court of Chancery’s finding that heavy
    reliance on extrinsic evidence in this case would be untenable because of the considerable passage
    of time. It stated, “[a]lthough [Daniel and Mr. Hawkins] generally seemed credible, their
    testimony about negotiations that occurred over two decades ago was not sufficiently reliable to
    support factual findings without corroboration.” Chancery Opinion, 273 A.3d at 833 n.45.
    Further, we conclude that the Court of Chancery’s factual finding regarding the structure’s
    temporary nature is supported by the record and is not clearly erroneous. Daniel’s view is
    particularly weakened by the language of the Irrevocable Proxy itself. The Termination Provision
    in the proxy explicitly contemplates that it will terminate upon the creation of a Newco. App. to
    Opening Br. at A035 (Irrevocable Proxy at 2, ¶ 5).
    30
    Chancery Opinion, 273 A.3d at 811 (noting that after pivoting to the Revised Settlement, in
    which only Old MedApproach acquired the Majority Shares, “PopCo [] insist[ed] on a mechanism
    to bind Old MedApproach to the Irrevocable Proxy”).
    31
    App. to Opening Br. at A034 (Irrevocable Proxy at 1).
    32
    Id. at A039 (Irrevocable Proxy at 5).
    14
    As requested by the LP Representatives,33 a majority of the interests in Danco LP
    approved the Revised Settlement. Mr. Hawkins transferred the amount of the Pike Loan
    to Pike and on February 11, 1997, Pike acknowledged receipt, resigned from his leadership
    positions, and transferred the Majority Shares to Old MedApproach. The next day, the
    parties to the litigation initiated by Popco approximately three months earlier, filed a
    stipulation of dismissal, dismissing the action with prejudice.34
    F. The Recission Offer and the Offering
    After approximately a year-long delay largely due to the loss of Danco Labs’
    primary manufacturing contract, Danco LP launched the Recission Offer and the Offering
    by circulating a confidential offering memorandum to its limited partners on August 5,
    1998 (the “Offering Memorandum”).35 The Offering Memorandum both informed limited
    partners of Danco LP about the Rescission Offer and sought to sell up to $27.5 million
    aggregate amount of limited partnership interests in Danco LP in the Offering. Of the
    $27.5 million, $13.35 million would be used to fund the Recission Offer to the extent
    limited partners chose to rescind, and at least the remaining $14.15 million would serve as
    additional funding for the Project.36 The Offering Memorandum described the history of
    33
    On January 31, 1997, the LP Representatives circulated a revised memorandum to the limited
    partners of Danco LP reflecting the changes and requesting their consent to (i) enter into the
    Revised Settlement, (ii) transfer interests in, and change control of, Danco GP, and (iii) transfer
    voting control of Danco GP to Daniel, Freeman, and Rush. Id. at A207 (Offering Memorandum
    at 76). The revised memorandum does not appear in the record, but it is described in the Offering
    Memorandum.
    34
    Id. at A208 (Offering Memorandum at 77).
    35
    Id. at A128, A190 (Offering Memorandum at 1, 59).
    36
    Id. at A137 (Offering Memorandum at 6).
    15
    the Project, Pike’s legal trouble, the Revised Settlement, and various Project risk factors,
    including risks relating to the control of Danco LP.37 It disclosed that limited partners of
    Danco LP lacked control over the entity and the Project because they did not have voting
    rights.38 Instead, Danco LP was managed and controlled exclusively by its general partner.
    As for Danco GP, the Offering Memorandum explained that it was “controlled by the [ ]
    Holders.”39 It also stated that:
    Pursuant to an Irrevocable Proxy and Power of Attorney, dated February 5,
    1997, [Old MedApproach], Mr. Pike and his wife granted to Messrs. Daniel
    and Freeman and Dr. Rush . . . proxies to vote their respective interests in
    [Danco GP]. Accordingly, [Danco GP] is in effect managed by or under the
    direction of the [ ] Holders.40
    Apart from disclosing the existence of the Irrevocable Proxy and the identities of the
    Holders, the Offering Memorandum was silent as to its terms. Importantly, it did not
    explicitly address whether the Irrevocable Proxy would bind any subsequent owner of the
    Majority Shares.41
    37
    See e.g., id. at A135–36, A141–55, A205–09 (Offering Memorandum at 4–5, 74–78, 10–24).
    38
    Id. at A149 (Offering Memorandum at 18) (“Therefore, except for certain extraordinary matters
    (such as admitting new or additional general partners, changing the nature of [Danco LP’s]
    business, acting in contravention of the Partnership Agreement, obtaining financing from affiliates
    of [Danco LP], or amending the Partnership Agreement), the Limited Partners have no voice in
    the day-to-day management of [Danco LP] or its business or affairs and have no voting rights.”).
    39
    Id.
    40
    Id. at A180 (Offering Memorandum at 49).
    41
    Chancery Opinion, 273 A.3d at 811 (“[Daniel’s] arguments tacitly concede that there is no
    provision in the Irrevocable Proxy which expressly states that it runs with the Majority Shares.”).
    16
    The Rescission Offer closed in 1999. It raised $23,901,966, falling short of its $27.5
    million goal.42 At trial, Mr. Hawkins estimated that he ultimately contributed $5–6 million
    to the Rescission Offer.
    G. Freeman Resigns
    After the Rescission Offer closed, Freemen sent a letter to Daniel and Rush dated
    May 17, 1999 (“Freeman Resignation Letter”).43 It informed them that he would no longer
    be serving as a Holder under the Irrevocable Proxy or a director of Danco GP. He explained
    that he was resigning in part because, “upon the completion or termination of the current
    financing, restructuring, [and] rescission efforts, the role of [ ] Holder is no longer
    necessary.”44 The Court of Chancery found that this “assertion evinces the pre-litigation
    understanding of a party closely involved in the settlement, and it indicates that the
    Irrevocable Proxy was not intended as a permanent control arrangement.”45 Freeman died
    in 2001, and since no one ever replaced Freeman as a Holder, Daniel and Rush are the only
    two remaining Holders. Rush is not a party to this litigation.
    H. The Restructuring of Old MedApproach
    After the Rescission Offer closed in 1999, Daniel caused Old MedApproach to
    undergo a significant restructuring. Old MedApproach dissolved and, upon its winding up,
    distributed its holdings across three newly formed Delaware limited partnerships: the
    42
    App. to Opening Br. at A572 (A. Van Vranken Trial Testimony at 250).
    43
    App. to Answering Br. at B362–63 (Freeman Resignation Letter).
    44
    Id. at B362.
    45
    Chancery Opinion, 273 A.3d at 804.
    17
    Partnership, DIG Special Assets, LP, and DIG Equity, LP. Daniel kept himself at the top
    of the new tri-entity structure. He is the 100% owner of his co-defendant, Holdings, the
    successor entity to Bio-Pharm Investments, Inc., and the general partner of the three
    MedApproach entities.
    As part of the restructuring, Old MedApproach distributed the Majority Shares to
    the Partnership, which is 88% owned by Mrs. Hawkins. Because of the Majority Shares,
    the Partnership owns 75% of Danco GP, with Pike still holding on to the remaining 25%.
    Consistent with its obligations under the Addendum as a MedApproach Person, the
    Partnership executed an Agreement To Be Bound by Irrevocable Proxy when it became
    the owner of the Majority Shares on January 1, 1999.46
    Mrs. Hawkins owns additional limited partnership interests in Danco LP through
    DIG Special Assets, LP and DIG Equity LP, but the two entities are otherwise not relevant
    to the question before the Court.
    The parties agreed that the following chart accurately represents the current
    organizational structure of the relevant entities. Med Approach Holdings is Holdings;
    MedApproach LP is the Partnership; N.D. Management is Danco GP; and Danco Investors
    Group, L.P. is Danco LP.
    46
    App. to Opening Br. at A370 (Agreement To Be Bound By Irrevocable Proxy And Power Of
    Attorney).
    18
    The economics of the Project flow from Danco Labs all the way up to Holdings.
    Danco Labs distributes all of its profits to its owner, Danco LP, which then distributes 20%
    of the profits to its general partner, Danco GP. Danco GP uses its 20% to pay dividends to
    its stockholders: The Partnership (in which Mrs. Hawkins has an 88% interest) receives
    75% of any dividend and Pike receives the remaining 25%. Danco LP distributes the
    remaining 80% of its share of Danco Lab’s profits to its limited partners. Through its
    19
    ownership of the Majority Shares and the limited partner interest in Danco LP, the
    Partnership receives approximately 17.71%47 of the profits generated by Danco Labs.48
    Holdings receives its piece of the pie as the general partner of the MedApproach
    entities. The Partnership pays Holdings a 1% management fee. Holdings also receives
    distributions on a 10% carried interest. As sole owner, Daniel receives the earnings of
    Holdings, net of expenses.49
    I. The End of the Pike Dispute and the Beginning of the Daniel/Hawkins Dispute
    By the end of the millennium, the Project had completed the Rescission Offer, raised
    additional funds through the Offering, and undergone a restructuring. In September 2000,
    the United States Food and Drug Administration approved mifepristone for sale in the
    United States. Finally, by 2001, the remnants of the Pike debacle were cleared up:
    Disputes with Pike were resolved and the financial obligations to him under the Settlement
    Agreement had been satisfied.
    47
    See Chancery Opinion, 273 A.3d at 805 n.17. As the owner of the Majority Shares, the
    Partnership receives 75% of 20% of Danco Labs’ profits. 75% multiplied by 20% equals 15%.
    The Partnership receives 2.71% of the profits of Danco Labs through the Partnership’s ownership
    of a limited partnership interest in Danco LP. 15% plus 2.71% equals 17.71%.
    48
    Id. at 805.
    49
    Daniel also receives considerable compensation for being a Holder. In a 1998 letter agreement,
    Old MedApproach acknowledged that Daniel would receive $300,000 per year from Danco LP
    and that Danco LP could reimburse Daniel for certain out-of-pocket expenses and additional
    special services he may provide. Ultimately, Daniel has earned approximately $10.3 million in
    proxy fees from Danco LP since 1996. He also receives $3,000 for each day spent on litigation
    involving the Project under an indemnification agreement with the Partnership, Danco GP, and
    Danco LP. Finally, Daniel earns income through an entity that leases office space to Danco GP
    and Danco LP.
    20
    With the threat of Pike asserting control over the Project ameliorated, Mr. Hawkins
    sought to terminate the Irrevocable Proxy.           Daniel informed Mr. Hawkins that the
    Irrevocable Proxy was irrevocable and could not be relinquished. As a result, the parties
    have filed a series of lawsuits against one another. 50 This litigation is the latest.
    J. The Parties’ Negotiations Over the Majority Shares
    The Partnership is governed by an Agreement of Limited Partnership dated as of
    January 1, 1999 (the “Partnership Agreement”). The Partnership Agreement provided that
    the Partnership shall terminate upon the expiration of its term, on December 31, 2020.
    As the expiration date approached, Daniel sought the approval of the limited
    partners of the Partnership to extend the term of the Partnership until 2045 to align with
    the term of Danco LP. The limited partners agreed, except for Mrs. Hawkins. Mrs.
    Hawkins agreed only to extend the term until February 28, 2021. Because Mrs. Hawkins
    owns 88% of the limited partnership interests in the Partnership, the Partnership dissolved
    on that date.
    The terms of the Partnership Agreement provide that after the Partnership dissolves,
    the only business to be conducted is completion of any pending transactions and the
    winding up of the affairs of the Partnership, including the distribution of its assets. The
    50
    Daniel’s entity, Holdings, initiated a suit in 2011 against Mr. and Mrs. Hawkins regarding
    management fees due to the entity. See MedApproach Hldgs., Inc. v. Hawkins, 
    2012 WL 6569268
    ,
    at *1 (M.D. Tenn. Dec. 17, 2012). The parties have settled the matter. See MedApproach Hldgs.,
    Inc. v. Hawkins, Civ. No. 3:11-cv-01199, ECF No. 125 (M.D. Tenn. Oct. 11, 2016). In 2021, the
    United States District Court for the Southern District of New York dismissed a 2013 action
    initiated by Mrs. Hawkins to invalidate the Irrevocable Proxy and resolve unrelated claims relating
    to the management of the MedApproach partnerships. See generally Hawkins v. Daniel (Dismissal
    Decision), 
    2021 WL 3732539
    , at *7–8 (Del. Ch. Aug. 24, 2021).
    21
    Partnership Agreement empowers its general partner, Holdings, to wind up the
    Partnership’s affairs. In doing so, Holdings is required to convert to cash the Partnership’s
    noncash assets and determine the capital accounts of its limited partners.
    On March 22, 2021, Mr. Hawkins sent a letter to Daniel, as owner of Holdings,
    conveying his interest in purchasing the Majority Shares in the winding up process. In his
    letter, Mr. Hawkins proposed a price in the range of $12 to $15 million, under the
    “threshold” condition that the Majority Shares be sold “free and clear from, and not subject
    to,” the Irrevocable Proxy.51
    On March 25, 2021, Daniel responded that any offer would have to “take into
    account the terms of the [Irrevocable] Proxy.”52 The next day, Daniel solicited offers from
    the other limited partners in Danco LP for the Majority Shares. Only Rush responded with
    an offer, proposing $5 million for 80% of the Partnership’s total assets based on the
    assumption that the Irrevocable Proxy would remain in place. The offer valued the
    Partnership at $6.125 million, approximately 50% lower than the bottom of the range
    proposed by Mr. Hawkins.
    The discussions between Mr. Hawkins and Daniel regarding the Majority Shares
    went nowhere. Neither of them was willing to budge on the issue of the Irrevocable Proxy.
    App. to Opening Br. at A455 (“Potential Offer to Purchase N.D. Management, Inc. Stock” dated
    51
    March 22, 2021).
    52
    
    Id.
     at A457 (“MedApproach Bid” dated March 25, 2021).
    22
    K. The Litigation
    On May 24, 2021, Mrs. Hawkins filed suit in the Court of Chancery asserting two
    counts against Daniel and Holdings. In Count I, Mrs. Hawkins sought a declaratory
    judgment that the defendants “are required to market and sell the Partnership’s 75% stake
    in [Danco GP] free and clear from, and not subject to, the continued application of the
    [Irrevocable] Proxy.”53 In Count II, she sought an injunction prohibiting the defendants
    “from marketing and/or selling the [Majority Shares] subject to the continued application
    of the [Irrevocable] Proxy.”54 She also sought expedited proceedings, and the trial court
    granted expedition.
    After dismissing a motion to dismiss filed by Daniel, the trial court held a one-day
    trial on September 23, 2021. At trial, Daniel agreed to postpone sale of the Majority Shares
    pending the outcome of this litigation. Post-trial briefing and argument moved forward on
    a non-expedited schedule, and the Court of Chancery issued its memorandum opinion on
    April 4, 2022. It entered judgment in favor of Mrs. Hawkins on May 9, 2022.
    In its memorandum opinion, the Court of Chancery summarized its conclusion as
    follows:
    The Irrevocable Proxy does not plainly provide that it binds a subsequent
    owner of the Majority Shares. There is language which might be construed
    in that fashion if read broadly and in Daniel’s favor, but that is not sufficient.
    The Addendum demonstrates that the parties themselves did not believe that
    the Irrevocable Proxy would bind a subsequent purchaser of the Majority
    Shares. The Addendum contains the Transfer Restriction [defined below],
    53
    
    Id.
     at A480–81.
    54
    
    Id.
     at A481.
    23
    but that provision does not encompass a third party [owner] of the Majority
    Shares.
    As a result, “the language of the Proxy itself does not plainly indicate that
    the Proxy [is] to run with the [s]hares if they are sold.” Accordingly, the
    Irrevocable Proxy does not run with the Majority Shares.55
    In short, the court held that “the plain language of the Irrevocable Proxy does not establish
    a grant of agency authority that runs with the Majority Shares.”56 Daniel filed notice of
    appeal on May 31, 2022. Oral argument was held on November 2, 2022.
    II.   SCOPE AND STANDARD OF REVIEW
    Daniel claims that the Court of Chancery erred as a matter of law in interpreting the
    language of the Irrevocable Proxy. Because irrevocable proxies are contracts, this is a
    question of contract interpretation. Contract interpretation is a question of law subject to
    de novo review by this Court.57 “Unless there is ambiguity, Delaware courts interpret
    contract terms according to their plain, ordinary meaning.”58 To the extent Daniel
    challenges the factual findings of the trial court, we will not disturb those findings “unless
    they are clearly erroneous and not supported by the record.”59 “Where there are two
    55
    Chancery Opinion, 273 A.3d at 832–33 (quoting TR Invs., LLC v. Genger, 
    2010 WL 2901704
    (Genger Trial), at *20 (Del. Ch. July 23, 2010), aff’d, 
    26 A.3d 180
     (Del. 2011)).
    56
    Id. at 812.
    57
    See, e.g., Genger v. TR Invs., LLC, 
    26 A.3d 180
    , 190 (Genger) (Del. 2011) (interpreting proxy);
    Stream TV Networks, Inc. v. Seecubic, Inc. (Stream TV), 
    279 A.3d 323
    , 336 (Del. 2022)
    (interpreting corporate charter).
    58
    Stream TV, 279 A.3d at 336 (quoting Alta Berkeley VI C.V. v. Omneon Inc., 
    41 A.3d 381
    , 385
    (Del. 2012)).
    59
    Genger, 
    26 A.3d at
    190 (citing Osborn ex rel. Osborn v. Kemp, 
    991 A.2d 1153
    , 1158 (Del.
    2010)).
    24
    permissible views of the evidence, the factfinder’s choice between them cannot be clearly
    erroneous.”60
    III.   ANALYSIS
    This Court must determine whether the Court of Chancery erred in finding that the
    Irrevocable Proxy does not run with the Majority Shares. Delaware public policy and law
    require that the terms of an irrevocable proxy be clear and unambiguous.61 Therefore, a
    Delaware court will not look to extrinsic evidence in interpreting an irrevocable proxy but
    will rely on the four corners of the proxy instrument itself. Where the irrevocable proxy is
    ambiguous, the ambiguity will be construed against the rights of the proxy holder.62
    As explained more fully below, we agree with the Court of Chancery, at least to the
    extent that the Irrevocable Proxy is ambiguous as to whether it binds subsequent third-
    party owners of the Majority Shares. As a result, it should be construed against the rights
    of the Holder, Daniel. That means the Irrevocable Proxy does not run with the Majority
    Shares in a sale to an unaffiliated third party.
    60
    Bank of New York Mellon Trust Co., N.A. v. Liberty Media Corp., 
    29 A.3d 225
    , 236 (Del. 2011).
    61
    Genger Trial, 
    2010 WL 2901704
     at *20 (finding that a proxy did not run with the shares because
    “the language of the Proxy itself does not plainly indicate that the Proxy was to run with the Shares
    if they are sold” and that “[e]ven if the language of the Proxy was ambiguous–which it is not–
    public policy concerns require that the Proxy be strictly construed”).
    62
    
    Id.
     See also Eliason v. Englehart, 
    733 A.2d 944
    , 947 (Del. 1999) (finding a proxy to be
    revocable where the words expressly stating that it was an “Irrevocable Proxy” were only found
    in the instrument’s signature acknowledgement, not in the language of the proxy itself).
    25
    A. Irrevocable Proxies Are Strictly Construed
    In the opinion below, the Court of Chancery recognized that “under the Delaware
    model, stockholders are presumed to vote in their economic interest.”63 When stockholders
    vote in their economic interests, the collective vote of the stockholders “serve[s] the
    ‘community of interest’ among all shareholders” and furthers the corporate goal of wealth
    maximization.64 This presumption underlies our Delaware courts’ preference to defer to
    the vote of disinterested stockholders. “[T]he long-standing policy of our law has been to
    avoid the uncertainties and costs of judicial second-guessing when the disinterested
    stockholders have had the free and informed chance to decide on the economic merits of a
    transaction for themselves.”65
    63
    Chancery Opinion, 273 A.3d at 808. See, e.g., Crown EMAK Partners LLC v. Kurz, 
    992 A.2d 377
    , 389 (Del. 2010) (affirming the Court of Chancery’s conclusion that no improper vote buying
    occurred since the economic and voting interests remained aligned when both sets of interests were
    transferred by the purchase agreement); Unitrin, Inc. v. Am. Gen. Corp., 
    651 A.2d 1361
    , 1380–81
    (Del. 1995) (noting that “stockholders are presumed to act in their own best economic interests
    when they vote in a proxy contest”).
    64
    Crown EMAK Partners LLC, 
    992 A.2d at
    388 (citing In re IXC Commc’ns, Inc. S’holders Litig.,
    
    1999 WL 1009174
    , at *8 (Del. Ch. Oct. 27, 1999)); see also Corwin v. KKR Fin. Hldgs. LLC, 
    125 A.3d 304
    , 314 (Del. 2015) (“In circumstances, therefore, where the stockholders have had the
    voluntary choice to accept or reject a transaction, the business judgment rule standard of review is
    the presumptively correct one and best facilitates wealth creation through the corporate form.”);
    Haft v. Haft, 
    671 A.2d 413
    , 421 (Del. Ch. 1995) (“A powerful argument can be advanced that
    generally the congruence of the right to vote and the residual rights of ownership will tend towards
    efficient wealth production.”).
    65
    Corwin, 
    125 A.3d at
    312–13; see also In re Lear Corp. S’holder Litig., 
    926 A.2d 94
    , 114–15
    (Del. Ch. 2007) (“Delaware corporation law gives great weight to informed decisions made by an
    uncoerced electorate. When disinterested stockholders make a mature decision about their
    economic self-interest, judicial second-guessing is almost completely circumscribed by the
    doctrine of ratification.”) (internal footnotes omitted)). This Court in Corwin explained the
    underlying rationale of our policy not to second-guess the informed choice of disinterested
    stockholders:
    26
    The legitimizing influence of a stockholder vote is premised upon the alignment of
    the economic and voting interests of stockholders. However, innovations in technology
    and finance have made it easier to separate the voting interests from the financial interests
    of shares.66 Early Delaware courts were suspicious of such arrangements.67 In Schreiber
    v. Carney,68 for example, our Court of Chancery examined the state of the law as it related
    When the real parties in interest—the disinterested equity owners—can easily
    protect themselves at the ballot box by simply voting no, the utility of a litigation-
    intrusive standard of review promises more costs to stockholders in the form of
    litigation rents and inhibitions on risk-taking than it promises in terms of benefits
    to them. The reason for that is tied to the core rationale of the business judgment
    rule, which is that judges are poorly positioned to evaluate the wisdom of business
    decisions and there is little utility to having them second-guess the determination
    of impartial decision-makers with more information (in the case of directors) or an
    actual economic stake in the outcome (in the case of informed, disinterested
    stockholders).”
    Corwin, 
    125 A.3d at
    313–14 (emphasis added) (internal footnote omitted).
    66
    Crown EMAK Partners LLC, 
    992 A.2d at
    387–88 (citing Robert B. Thompson & Paul H.
    Edelman, Corporate Voting, 
    62 Vand. L. Rev. 129
    , 153 (2009)). Innovations have also led to the
    rise in dual-, multi-, and zero-class voting structures, as opposed to the “one share-one vote”
    default rule memorialized in our 8 Del. C. § 212(a). See David T. White, Delaware’s Role in
    Handling the Rise of Dual-, Multi-, and Zero-Class Voting Structures, 
    45 Del. J. Corp. L. 141
    (2020); Thompson & Edelman, supra, at 158–60.
    67
    See e.g., Oceanic Exploration Co. v. Grynberg, 
    428 A.2d 1
    , 7 (Del. 1981) (observing that
    “[v]oting trusts were viewed with ‘disfavor’ or ‘looked upon . . . with indulgence’ by the courts”
    and “other contractual arrangements interfering with stock ownership, such as irrevocable proxies,
    were viewed with suspicion’”) (citing Perry v. Missouri-Kansas Pipe Line Co., 
    191 A. 823
    , 827
    (Del. Ch. 1937))); Haft, 
    671 A.2d at 421
     (“[I]t is appropriate to acknowledge that the corporate
    law has tended to distrust and discourage the separation of the shareholder claim as equity investor
    (i.e., the right to enjoy distributions on stock if, as, and when declared) from the right to vote stock.
    For example there was for many years a rather clear rule against the sale of a corporate vote
    unattached to the sale of the underlying stock.”) (internal footnote omitted) (evaluating whether a
    proxy was irrevocable); Commonwealth Assocs. v. Providence Health Care, Inc, 
    641 A.2d 155
    ,
    157 (Del. Ch. 1993) (“The law has long discouraged the sale of votes unconnected to the sale of
    stock.”); Macht v. Merchants Mortgage & Credit Co., 
    194 A. 19
    , 22 (Del. Ch. 1937) (“To allow
    voting rights that are bought to be exercised is against public policy, and would be in fraud of the
    other stockholders.”).
    68
    
    447 A.2d 17
     (Del. Ch. 1982).
    27
    to vote-buying.69 It clarified that “an agreement involving the transfer of stock voting
    rights without the transfer of ownership is not necessarily illegal and each arrangement
    must be examined in light of its object or purpose.”70
    Nearly three decades later, this Court, in Crown EMAK Partners LLC, again
    examined a challenged vote-buying arrangement. We recognized that the separation of
    voting power and economic interest should be subject to greater scrutiny because it
    “compromises the ability of voting to perform its assigned role.”71 We affirmed the Court
    of Chancery’s conclusion that no improper vote buying had occurred in that case “because
    the economic interests and the voting interests of the shares remained aligned.”72 We
    explained:
    For many years, Delaware decisions have expressed consistent concerns
    about transactions that create a misalignment between the voting interest and
    the economic interest of shares. As then Vice–Chancellor (now Chief Justice)
    69
    The Schreiber court defined vote-buying as “a voting agreement supported by consideration
    personal to the stockholder, whereby the stockholder divorces his discretionary voting power and
    votes as directed by the offeror.” 
    Id. at 23
    .
    70
    
    Id. at 25
    .
    71
    Crown EMAK Partners LLC, 
    992 A.2d at
    388 (citing Thompson & Edelman, supra note 66, at
    153). The Crown EMAK Court further quoted Thompson and Edelman: “They concluded that ‘[a]
    decisionmaking system that relies on votes to determine the decision of the group necessarily
    requires that the voters’ interest be aligned with the collective interest. [Therefore, i]t remains
    important to require an alignment between share voting and the financial interest of the shares.”
    Id. (alteration in original); see also Commonwealth Assocs., 
    641 A.2d at 157
     (noting law’s historic
    concern about “the sale of votes unconnected to the sale of stock” in part because “such sales
    misalign the interests of voters and the interests of the residual corporate risk bearers”).
    Accordingly, Delaware law requires that an irrevocable proxy be “coupled with an interest”
    whether “in the stock itself” or “in the corporation generally.” 8 Del. C. § 212(e) (“A duly executed
    proxy shall be irrevocable if it states that it is irrevocable and if, and only as long as, it is coupled
    with an interest sufficient in law to support an irrevocable power. A proxy may be made
    irrevocable regardless of whether the interest with which it is coupled is an interest in the stock
    itself or an interest in the corporation generally.”).
    72
    Crown EMAK Partners LLC, 
    992 A.2d at 390
    .
    28
    Steele explained, “[g]enerally speaking, courts closely scrutinize vote-
    buying because a shareholder who divorces property interest from voting
    interest [ ] fails to serve the ‘community of interest’ among all shareholders,
    since the ‘bought’ shareholder votes may not reflect rational, economic self-
    interest arguably common to all shareholders.” Again, in this case, the Court
    of Chancery recognized that “[w]hat legitimizes the stockholder vote as a
    decision-making mechanism is the premise that stockholders with economic
    ownership are expressing their collective view as to whether a particular
    course of action serves the corporate goal of stockholder wealth
    maximization.”73
    A proxy instrument is evidence of an agency relationship wherein the beneficial
    owner-principal appoints a proxy holder-agent as attorney-in-fact with respect to the voting
    rights of the shares.74 Thus, by its very nature, a proxy, which temporarily splits the power
    to vote from the residual ownership claim of the stockholder, has the potential to create
    misalignment between the voting interest and the economic interest of shares. As the Court
    of Chancery noted, the risks of significant divergence of interests between the proxy holder
    and the holder of the residual interests are enhanced where the proxy is irrevocable. That
    is because an irrevocable proxy, unlike a revocable proxy which is typically of relatively
    short duration and is revocable by the grantor, frees the holder from “the unilateral control
    of the grantor.”75 Here, not only is the proxy arrangement irrevocable, but Daniel asks this
    73
    Crown EMAK Partners LLC, 
    992 A.2d. at 388
     (first quoting In re IXC Commc’s, Inc. S’holders
    Litig., 
    1999 WL 1009174
    , at *8; then quoting Kurz v. Holbrook, 
    989 A.2d 140
    , 178 (Del. Ch.
    2010)).
    74
    See Eliason, 
    733 A.2d at 946
     (“A proxy is evidence of an agent’s authority to vote shares owned
    by another.”) (citing Duffy v. Loft, Inc., 
    151 A. 223
    , 227 (Del. Ch.), aff’d, 
    152 A. 849
     (Del.
    1930))); Moran v. Household Int’l, Inc., 
    500 A.2d 1346
    , 1355 (Del. 1985) (“[I]t has long been
    recognized that the relationship between grantor and recipient of a proxy is one of agency, and the
    agency is revocable by the grantor at any time.”).
    75
    Haft, 
    671 A.2d at 421
    .
    29
    Court to find that it runs with the Majority Shares, binding a future owner to an agent that
    may or may not be economically aligned.
    As our approach to vote-buying arrangements and voting trusts has liberalized with
    innovations in technology and finance, so, too, has our approach to proxy arrangements. 76
    Still, because of the concerns arising from a decoupling of the voting and economic interest
    in shares, “[h]istorically, proxies have been interpreted narrowly and when there is an
    ambiguity, read as not restricting the right to vote the shares.”77 When interpreting an
    irrevocable proxy, Delaware courts do not turn to extrinsic evidence to resolve an
    ambiguity. Rather, they construe the irrevocable proxy in favor of the rights of the
    76
    See Oceanic Exploration Co. v. Grynberg, 
    428 A.2d 1
    , 7 (Del. 1981). In finding that the trial
    court erred in holding that a contract among stockholders was a “voting trust” within the meaning
    of 8 Del. C. § 218(a) and (b), we observed:
    [I]t is important to recognize there has been a significant change from the days of
    our original 1925 statute. Voting trusts were viewed with “disfavor” or “looked
    upon . . . with indulgence” by the courts. Other contractual arrangements
    interfering with stock ownership, such as irrevocable proxies, were viewed with
    suspicion. The desire for flexibility in modern society has altered such restrictive
    thinking. The trend of liberalization was markedly apparent in the 1967 changes to
    our own [8 Del. C. § 218]. Voting or other agreements and irrevocable proxies were
    given favorable treatment and restrictive judicial interpretations as to the absolute
    voiding of voting trusts for terms beyond the statutory limit were changed by
    statute.
    Id. (alteration in original) (citing E. FOLK, The Delaware General Corporation Law § 218 at 240–
    42 (1972)).
    Further, in 1967, the General Assembly amended 8 Del. C. § 212(c) (now § 212(e)) to clarify that
    a proxy may be made irrevocable “regardless of whether the interest with which it is coupled is an
    interest in the stock itself or an interest in the corporation generally.” 8 Del. C. § 212(e). The
    language added in 1967 (“an interest in the corporation generally”) was intended to address a
    suggestion in In re Chilson, 
    168 A. 82
     (Del. Ch. 1933) that in order to support irrevocability, the
    holder had to have an interest in the stock itself.
    77
    Genger Trial, 
    2010 WL 2901704
    , at *20.
    30
    beneficial owner of the shares.78 Here, the Irrevocable Proxy does not run with the
    Majority Shares unless its plain language clearly and unambiguously provides that it
    does.79 The Court of Chancery read the Irrevocable Proxy as a whole, painstakingly
    examining the preamble, recitals, each operative provision, and the Addendum, and
    concluded that it does not. For the reasons discussed below, we agree.
    B. The Plain Language of the Irrevocable Proxy
    On appeal, Daniel contends that the plain language of the Irrevocable Proxy
    provides that it runs with the Majority Shares and that the Court of Chancery erred in three
    ways in concluding otherwise.           Daniel’s first two arguments concern the provision
    regarding non-termination of the Irrevocable Proxy (the “Non-Termination Provision”).
    His final argument concerns the provision governing assignment of rights under the
    Irrevocable Proxy (the “Assignment Provision”). Daniel does not challenge other of the
    Court of Chancery’s findings supporting its opinion.80
    78
    See 
    id.
     (finding that because “language of the Proxy itself does not plainly indicate that the Proxy
    was to run with the Shares if they are sold,” they did not and that “[e]ven if the language of the
    Proxy was ambiguous . . . public policy concerns require that the Proxy be strictly construed”).
    79
    See generally Urdan v. WR Cap. Partners, LLC, 
    2019 WL 3891720
    , at *11 (Del. Ch. Aug. 19,
    2019) (“If a seller wishes to retain a subset of the rights associated with the transferred shares, such
    as the right to assert a direct claim, then the parties to the transaction must provide specifically for
    that outcome.”), aff’d, 
    244 A.3d 668
     (Del. 2020); In re Activision Blizzard, Inc. S’holder Litig.,
    
    124 A.3d 1025
    , 1050 (Del. Ch. 2015) (“When a share of stock is sold, the property rights associated
    with the shares, including any claim for breach of those rights and the ability to benefit from any
    recovery or other remedy, travel with the shares.”).
    80
    The Irrevocable Proxy provides that its terms shall be governed by the law of the State of
    California “[e]xcept to the extent required by the corporate or other provisions of the laws of the
    Cayman Islands.” App. to Opening Br. at A035 (Irrevocable Proxy at 2, ¶ 3). Despite the
    Irrevocable Proxy’s choice of law provision, the parties have relied almost entirely on Delaware
    law in litigating this case. We, like the Court of Chancery, follow the parties’ lead and interpret
    the Irrevocable Proxy according to Delaware law. Chancery Opinion, 273 A.3d at 810 n.21.
    31
    We first address several findings of the Court of Chancery which Daniel does not
    challenge on appeal, but which support our conclusion that the Irrevocable Proxy does not
    run with the Majority Shares. We then address each of Daniel’s arguments in turn.
    1. The Court of Chancery’s Unchallenged Findings
    The Court of Chancery began its analysis of the Irrevocable Proxy with an overview
    of its plain language. It found that (1) the definitions of “Stockholder” and “Shares” in the
    preamble, (2) the plain language of the Appointment Provision (defined below), and (3)
    the presence of the Addendum, all weighed in favor of Appellee’s reading of the
    Irrevocable Proxy.81 Daniel does not challenge these findings on appeal. The force of
    these unchallenged findings undermines Daniel’s arguments that the Court of Chancery
    erred in finding that the Irrevocable Proxy runs with the Majority Shares.
    a. The Definitions of “Stockholder” and “Shares” Limit the Irrevocable Proxy to
    Only Those Shares Owned By Pike, Then By Old MedApproach, and Now By the
    Partnership
    The Irrevocable Proxy is the instrument by which the owner of the Majority Shares
    granted the Holders the authority to exercise the Majority Shares’ attendant voting rights.
    The preamble of the Irrevocable Proxy defines the “Stockholder” as “Joseph D. Pike.”82 It
    does not include language that would include subsequent holders of the Majority Shares.
    The Addendum provides that, at any time that Old MedApproach or a MedApproach
    81
    The trial court’s opinion discusses additional recitals which it analyzed in the context of Daniel’s
    suggestion that the Irrevocable Proxy was intended to be a permanent corporate governance
    arrangement. See supra note 29.
    82
    App. to Opening Br. at A034 (Irrevocable Proxy at 1).
    32
    Person holds the Proxy Shares, all references to “Stockholder” in the Irrevocable Proxy
    shall refer to the MedApproach stockholder.83 Therefore, every reference to “Stockholder”
    in the Irrevocable Proxy is only to Pike initially, then Old MedApproach, and now, to the
    Partnership.84
    The first recital in the Irrevocable Proxy defines the “Shares” as “an aggregate of
    100 shares [ ] of the Common Stock, $1.00 par value, of [Danco GP]” of which “the
    Stockholder is the sole beneficial owner.”85 In other words, they are the “Shares” that were
    owned by Pike at the time he executed the Irrevocable Proxy. 86 Now they are the “Shares”
    owned by the Partnership.
    The narrow definitions of “Stockholder” and “Shares,” carried through the
    Addendum and the Agreement To Be Bound, do not evince an intent by the parties for the
    Irrevocable Proxy to run with the Majority Shares. Instead, the two definitions cabin the
    applicability of the Irrevocable Proxy to those shares owned by Old MedApproach or any
    other MedApproach Person who has agreed to be bound by the Irrevocable Proxy and has
    become a “Stockholder.” In short, as the Court of Chancery found, “there is nothing in the
    83
    Id. at A039 (Irrevocable Proxy at 5).
    84
    See id. at A370 (Agreement To Be Bound By Irrevocable Proxy And Power Of Attorney) (“[The
    Partnership] hereby joins, becomes a party to, and agrees to be bound as a ‘Stockholder’ by the
    provisions, terms and conditions of, and shall be entitled to all rights, benefits and remedies as a
    ‘Stockholder’ under [the Irrevocable Proxy] . . . .”).
    85
    Id. at A034 (Irrevocable Proxy at 1).
    86
    Chancery Opinion, 273 A.3d at 813.
    33
    preamble or recitals standing alone that would suggest the Irrevocable Proxy runs with the
    Majority Shares.”87
    b. The Appointment Provision Indicates the Holders Are Only Appointed as to the
    Shares Pike Owned During the Term of the Irrevocable Proxy
    The first operative provision of the Irrevocable Proxy is the provision that grants
    Daniel, Freeman, and Rush the power to exercise the Proxy Shares’ voting rights (the
    “Appointment Provision”).88 The Appointment Provision states in relevant part:
    The Stockholder hereby constitutes and appoints each Holder, during the
    term of this Irrevocable Proxy, as the Stockholder’s true and lawful proxy
    and attorney-in-fact, with full power of substitution, to vote all of the Shares
    plus any additional Shares which Stockholder may own or hold as of the date
    of any such vote (and any all [sic] securities issued or issuable in respect
    thereof) which Stockholder is entitled to vote (collectively, the “Proxy
    Shares”), for and in the name, place and stead of the Stockholder, at any
    annual, special or other meeting of the stockholders of the Company, and at
    any adjournment or postponement thereof, or pursuant to any consent in lieu
    of a meeting or otherwise.89
    This Court examined a similar appointment provision in Genger,90 where it upheld
    the Court of Chancery’s finding that the proxy there did not run with the associated shares.
    The appointment provision of the proxy in Genger provided that:
    The [Sagi Trust] . . . does hereby constitute and appoint Arie Genger . . . to
    vote as its proxy, all shares of common stock of [Trans–Resources] which
    87
    Id. at 814.
    88
    The Appointment Provision creates the agency relationship under Delaware law. It both
    appoints someone — the Holders — to vote the shares, see Loboto v. Health Concepts IV, Inc.,
    
    606 A.2d 1343
    , 1347 (Del. Ch. 1991), and “identif[ies] the shares to be voted by the agent,”
    Eliason, 
    733 A.2d at 946
    .
    89
    App. to Opening Br. at A034 (Irrevocable Proxy at 1, ¶ 1).
    90
    
    26 A.3d 180
    .
    34
    are now or hereafter owned by the Trust, at any and all meetings of the
    stockholders of Trans–Resources . . . .91
    This Court looked at the proxy’s plain language and agreed that the proxy “would
    attach only to those [Trans–Resources] shares that were ‘now or hereafter owned by the
    Trust.’”92 Because there was no provision explicitly providing that shares owned by a
    subsequent owner would be covered by the proxy and the proxy plainly only applied to
    those shares “owned by the Trust,” the proxy did not run with the shares at issue.93
    Here, the Appointment Provision states that Pike, as the Stockholder, appointed the
    Holders to be his proxy and attorney-in-fact “to vote all of the Shares plus any additional
    Shares which Stockholder may own or hold as of the date of any such vote (and any all [sic]
    securities issued or issuable in respect thereof) which Stockholder is entitled to vote.” The
    Appointment Provision here goes one step further than that in Genger, clarifying that the
    Holders may vote the shares “for and in the name, place and stead of the Stockholder.” As
    in Genger, by its plain language, the appointment is only with respect to shares of Danco
    GP owned by “the Stockholder” at the time of a vote and the authority only extends as far
    as that of the Stockholder. As discussed above, because “Stockholder” is defined only as
    Pike, and later Old MedApproach and the Partnership, the provision indicates that the
    Irrevocable Proxy does not run with the Majority Shares.
    91
    
    Id. at 198
     (alteration in original) (emphasis in original).
    92
    
    Id.
    93
    
    Id.
     (“The Proxy contains no provision that would bind any subsequent owner of those shares.
    Once sold or transferred to a subsequent owner, those shares were no longer ‘owned by the [Sagi]
    Trust’ and therefore, were no longer subject to the Proxy.”) (emphasis in original).
    35
    c. The Addendum Demonstrates That the Drafters Did Not Intend Subsequent Buyers
    to Be Bound by The Irrevocable Proxy Absent Their Agreement to Be Bound
    As discussed above, the initial Settlement Agreement contemplated that certain
    Participating Investors, defined as Old MedApproach, Freeman, Rush, and importantly,
    any other limited partner of Danco LP who wanted to sign onto the Settlement Agreement,
    would fund the Pike Loan to purchase the Majority Shares from Pike. Days later, the LP
    Representatives determined that offering the opportunity to all limited partners of Danco
    LP was impracticable and threatened to delay the deal, so the parties agreed instead that
    Old MedApproach alone would purchase the Majority Shares.                      As a result, Old
    MedApproach executed the Addendum, agreeing to be bound to the Irrevocable Proxy once
    it received the Majority Shares from Pike.94
    Daniel testified that the Addendum was prepared primarily by Popco’s attorney and
    executed at its request.95 The Addendum, described by the Court of Chancery as a “drafting
    monstrosity” and “not a model of clarity,”96 consists entirely of the following paragraph:
    At any time that [Old MedApproach], or its affiliates, owners, designees or
    nominees (or their respective successors or assigns) (each a “MedApproach
    Person”) is a beneficial or record holder of any of the Shares or any of the
    Proxy Shares, [Old MedApproach] hereby agrees (and agrees to cause each
    other MedApproach Person to agree) that references in this Irrevocable
    Proxy to “Stockholder” shall mean and include [Old MedApproach] (or such
    MedApproach Person) with references to “the date hereof” in Section 2(a)
    being instead a reference to the date of closing under the Agreement), and
    94
    Chancery Opinion, 273 A.3d at 829.
    95
    See id. at 829; App. to Opening Br. at A546 (W. B. Daniel Trial Testimony at 146–47). The
    trial court found that Popco’s attorney “did not believe that the language of the Irrevocable Proxy,
    standing alone, was sufficient to bind Old MedApproach to the Irrevocable Proxy.” Chancery
    Opinion, 273 A.3d at 829.
    96
    Chancery Opinion, 273 A.3d at 830.
    36
    that [Old MedApproach] is bound (and [Old MedApproach] agrees not to
    transfer any such shares to any other MedApproach Person unless such
    transferee agrees in writing satisfactory to the [ ] Holders (other than W.
    Bradley Daniel) to be bound) by this Irrevocable Proxy as the Stockholder;
    provided, however, no MedApproach Person shall be deemed the
    Stockholder for purposes of Section 2 hereof. [Old MedApproach] agrees to
    duly authorize, execute and deliver a restated Irrevocable Proxy reflecting
    the foregoing promptly after the closing under the Agreement and such other
    agreements or documents as are reasonably necessary or appropriate to carry
    out the intent of the foregoing.97
    The existence of the Addendum suggests that the parties to the Irrevocable Proxy,
    and Popco, understood at the time of its execution that the Irrevocable Proxy would not run
    with the Majority Shares. If the terms of the Irrevocable Proxy provided it would run with
    the Majority Shares, then there would be no need to execute an Addendum to bind Old
    MedApproach. In short, the court found that “the parties entered into the Addendum to
    ensure that the Irrevocable Proxy would bind the one subsequent owner that they knew
    about — Old MedApproach.”98
    The Addendum not only provides that Old MedApproach will become a
    “Stockholder” for purposes of the Irrevocable Proxy, but also, it contains a transfer
    restriction at the end of the first sentence (the “Transfer Restriction”). The Court of
    Chancery found that the Transfer Restriction (1) “applies to any transfer by one
    MedApproach Person to another MedApproach Person,” and (2) that “a MedApproach
    Person only means an entity or individual affiliated with Old MedApproach, not a third
    97
    App. to Opening Br. at A039–40 (Irrevocable Proxy at 5–6).
    98
    Chancery Opinion, 273 A.3d at 814.
    37
    party.”99 Accordingly, the Transfer Restriction obligates Old MedApproach to ensure that
    in any transfer to an affiliated entity, the affiliated entity agrees to be bound by the
    Irrevocable Proxy. Further, the Addendum does not restrict a transfer to an unaffiliated
    third party.100
    The Transfer Restriction demonstrates that the parties to the Irrevocable Proxy did
    not believe that it ran with the Majority Shares upon their sale. If it did run with the
    Majority Shares, then there would be no need for the Transfer Restriction, let alone the
    Addendum. Any buyer of the Majority Shares would already be bound by the Irrevocable
    Proxy by its terms and there would be no need for the MedApproach Person-seller to
    enforce the proxy against any MedApproach Person-buyer. The Transfer Restriction also
    demonstrates that the parties knew how to restrict a transfer of the Majority Shares but only
    elected to apply that restriction to a narrow set of transfers.101
    These three aspects of the Irrevocable Proxy — the definitions of Stockholder and
    Shares, the language in the Appointment Provision, and the presence of the Addendum and
    Transfer Restriction — all indicate that the parties did not intend the Irrevocable Proxy to
    run with the Majority Shares. In the face of these findings, along with the need to show in
    clear and unambiguous language that the Irrevocable Proxy runs with the Majority Shares,
    Daniel faces an uphill battle in demonstrating that the Court of Chancery erred. To win
    99
    Id. at 832.
    Id. The trial court’s unchallenged interpretation of the Transfer Restriction reinforces that the
    100
    Addendum does not restrict a transfer to an unaffiliated third party (i.e., persons other than a
    MedApproach Person).
    101
    Id.
    38
    the battle, he must show that the remaining provisions of the Irrevocable Proxy
    unambiguously overcome the foregoing plain language. As explained below, Daniel fails
    in his challenge.
    2. The Non-Termination Provision
    Daniel’s first two arguments on appeal concern the Non-Termination Provision in
    the Irrevocable Proxy. He argues that the Non-Termination Provision “memorialized the
    parties’ intent for the proxy to survive a sale of the shares and bind subsequent owners.”102
    The Non-Termination Provision, found in paragraph five of the Irrevocable Proxy, reads
    in its entirety, as follows:
    The Stockholder agrees that such Irrevocable Proxy is coupled with an
    interest sufficient in law to support an irrevocable power and shall not be
    terminated by any act of the Stockholder (other than in connection with the
    termination provisions of Section 4 hereof), by death or disability of the
    Stockholder, by lack of appropriate power or authority or by the occurrence
    of any other event or events other than as provided in Section 4 hereof.103
    Daniel argues that the words “by any act of the Stockholder” and “or by the occurrence of
    any other event or events” include the sale of the Majority Shares by the Stockholder.
    Therefore, a sale of the Majority Shares by the Stockholder would not terminate the
    Irrevocable Proxy. Under Daniel’s reading, the provision “communicates that only the
    circumstances of Section 4 may result in termination of the Irrevocable Proxy.”104
    102
    Opening Br. at 21.
    103
    App. to Opening Br. at A035 (Irrevocable Proxy at 2, ¶ 5) (emphasis added).
    Opening Br. at 21. The Court of Chancery referred to Section 4 as the “Termination Provision.”
    104
    The Termination Provision provides that:
    This Irrevocable Proxy shall terminate immediately upon the occurrence of any of
    the following: (i) the merger or other reorganization of [Danco GP] in connection
    39
    The Court of Chancery rejected Daniel’s reading of the Non-Termination Provision.
    It found that “the more natural reading is that the Non-Termination Provision confirms that
    the Stockholder cannot terminate the Irrevocable Proxy while owning the Majority Shares”
    but “does not say anything about whether the Irrevocable Proxy binds a subsequent
    owner.”105
    On appeal, Daniel argues that the Court of Chancery erred with respect to the Non-
    Termination Provision in two ways: (1) first, it erroneously read the provision, primarily
    the language “by any act of the Stockholder,” against default principles in the Restatement
    (Third) of Agency, which themselves are contrary to Delaware law,106 and (2) second, it
    effectively read additional language into the provision to conclude that the broad catch-all
    language “any other event or events” did not include a sale of the Majority Shares. 107 We
    address each argument in turn.
    a. The Court of Chancery’s Reference to Default Principles of Common Law Was
    Not Essential to its Holding
    Daniel argues that the phrase “any act of the Stockholder” in the Non-Termination
    Provision includes the sale of the Majority Shares by the Stockholder. The Court of
    with the formation of “Newco” as contemplated in the [Settlement Agreement], but
    only if and to the extent the terms and conditions of the documentation pursuant to
    which such merger or other reorganization is effected expressly refer to this
    Irrevocable Proxy and expressly provide that this Irrevocable Proxy shall terminate
    pursuant to such documents; or (ii) upon notice of termination given by the Holders
    to the Stockholder. App. to Opening Br. at A035 (Irrevocable Proxy at 2, ¶ 4).
    105
    Chancery Opinion, 273 A.3d at 819.
    106
    Opening Br. at 22–23.
    107
    Id. at 28.
    40
    Chancery concluded that Daniel’s reading was “one possible reading” but “[t]he better
    reading is that the concept of an ‘act of the Stockholder’ encompasses acts that the principal
    might take to terminate the agency relationship while remaining the owner of the Majority
    Shares.”108
    Explaining why its reading was the better one, the Court of Chancery determined
    that the Non-Termination Provision tracks the following categories in Section 3.13 of the
    Restatement (Third) of Agency wherein, “[u]nless otherwise agreed, neither a power given
    as security nor a proxy made irrevocable” will be terminated by:
    (a) a manifestation revoking the power or proxy made by the person who
    created it; or
    ...
    (c) loss of capacity by the creator or the holder of the power or proxy; or
    ...
    (e) death of the creator of the power or proxy, if the power or proxy is given
    as security for the performance of a duty that does not terminate with the
    death of its creator.109
    According to the Court of Chancery, the language “by any act of the Stockholder” reflects
    the common law principle stated in clause (a) of the Restatement that “a manifestation
    revoking the power or proxy made by the person who created it” will not terminate an
    irrevocable proxy “[u]nless otherwise agreed.”110 Thus, it found that the Non-Termination
    108
    Chancery Opinion, 273 A.3d at 820.
    109
    RESTATEMENT (THIRD) OF AGENCY § 3.13(2) (Am. Law. Inst. 2006), available at Westlaw
    (database updated Oct. 2022).
    110
    Chancery Opinion, 273 A.3d at 819, 820. Daniel similarly argued that the phrase “death or
    disability of the Stockholder” in the Irrevocable Proxy should be read to include the dissolution
    and winding up of the Partnership. The Court of Chancery rejected Daniel’s “death or disability”
    argument, concluding that “death or disability” is materially different than dissolution and that the
    phrase, instead, mirrored the common law principles stated in clause (c) and (e) of the Restatement.
    41
    Provision, “is not a bespoke provision designed to make the Irrevocable Proxy run with the
    Majority Shares.”111
    Moreover, it determined that Daniel’s reading of the phrase “any act of the
    Stockholder” conflicts with the common law principles in the Restatement.112 In Section
    3.13(1), the Restatement (Third) provides:
    A power given as security or an irrevocable proxy is terminated by an event
    that
    (a) discharges the obligation secured by the power or terminates the
    interest secured or supported by the proxy, or
    (b) makes its execution illegal or impossible, or
    (c) constitutes an effective surrender of the power or proxy by the
    person for whose benefit it was created or conferred.113
    Comment b to Section 3.13 explains that, under the above circumstances “irrevocable
    proxies will always terminate.”114
    Accordingly, the Court of Chancery concluded that, absent express language to the
    contrary, a sale of shares that is the subject of an irrevocable proxy terminates the
    irrevocable proxy under the principle stated in clause (b). This is because:
    Id. at 821–22 (“There are multiple difficulties with Daniel’s reading. First, death is not the same
    as dissolution . . . Second, the reference to ‘death or disability’ tracks the common law concepts
    framed in Sections 3.13(2)(c) and (e) of the Restatement . . . The clear distinction between the
    consequences of death or disability and the consequences of a sale mean that the reference to ‘death
    or disability’ in the Irrevocable Proxy does not cause the Irrevocable Proxy to run with the Majority
    Shares.”). Daniel does not challenge this finding on appeal.
    111
    Id. at 819–20.
    112
    Id. at 820.
    113
    RESTATEMENT (THIRD) OF AGENCY § 3.13(1).
    114
    Id. at § 3.13 cmt. b.
    42
    After a sale, the grantor no longer has the right to vote the shares that are the
    subject of the proxy. Instead, the right belongs to the subsequent owner. The
    proxyholder cannot exercise the grantor’s right to vote because the grantor
    no longer possesses that right. Consequently, absent specific and express
    language to the contrary, an irrevocable proxy terminates “when it is no
    longer possible for the proxyholder to vote because the grantor of the proxy
    no longer owns the securities or membership interest.”115
    The Court of Chancery added that “[o]nly if the purchaser both knows about an irrevocable
    proxy and the irrevocable proxy contains plain and unambiguous language binding a
    subsequent owner will the purchaser acquire the shares subject to the irrevocable proxy.”116
    Daniel articulates three reasons why the Court of Chancery’s reliance on the
    Restatement (Third) of Agency constitutes legal error. Although we address Daniel’s
    arguments for completeness, we conclude that the Court of Chancery’s discussion of the
    Restatement was not essential to its ultimate holding, and regardless of the merits (or lack
    thereof) of his contentions about the Restatement, Daniel still fails to show that the
    Irrevocable Proxy clearly and unambiguously provides that it runs with the Majority
    Shares.
    i.      Daniel’s Reliance on Stream TV is Misplaced
    First, Daniel argues that the trial court’s finding that the Irrevocable Proxy “tracked”
    three of the five termination events listed in the Restatement was erroneous, and therefore,
    115
    Chancery Opinion, 273 A.3d at 820 (quoting RESTATEMENT (THIRD) OF AGENCY § 3.13 cmt.
    b).
    116
    Id. (emphasis in original).
    43
    under this Court’s decision in Stream TV,117 it was improper for the trial court to rely on
    the Restatement (Third) to interpret the contractual language.118
    Daniel’s’ reliance on Stream TV is misplaced. The question before this Court in
    Stream TV was whether the approval of the Class B stockholders of Stream TV Networks,
    Inc. (“Stream Inc.”), was required before Stream Inc. could enter into an agreement to
    transfer and assign all rights, title and interest in all of the company’s assets for the benefit
    of certain of its creditors (the “Stream Omnibus Agreement”).119          Stream Inc.’s charter
    provided that a majority vote of the Class B stockholders was required for the company to
    undertake certain corporate actions, including an “Asset Transfer.” The charter defined
    “Asset Transfer” as a “sale, lease or other disposition of all or substantially all of the assets
    or intellectual property” of Stream Inc., and the granting of certain intellectual property
    licenses of Stream Inc.120 This Court found that the plain meaning of “other disposition”
    included the transfer and assignment of all rights, title and interest in all of the company’s
    assets for the benefit of its creditors.121 Therefore, the Stream Omnibus Agreement needed
    to be approved by the majority of Stream Inc.’s Class B stockholders.
    In so holding, this Court reversed the Court of Chancery’s determination that Stream
    Inc.’s board of directors unilaterally could cause Stream Inc. to enter into the Stream
    117
    
    279 A.3d 323
    .
    118
    Opening Br. at 23–24.
    119
    Stream TV, 279 A.3d at 340.
    120
    Id. at 338 (emphasis added).
    121
    Id. at 340.
    44
    Omnibus Agreement. The Court of Chancery had found that although the Stream Omnibus
    Agreement contemplated an “Asset Transfer,” the charter provision “tracked” Section 271
    of the Delaware General Corporation Law and thus “warrant[ed] the same
    interpretation.”122 Rather than looking to the plain language of Stream Inc.’s charter, the
    Court of Chancery looked to Section 271 as an interpretive guide. It found that at the time
    of the enactment of Section 271’s predecessor statute, there was a common law insolvency
    exception in Delaware which allowed an insolvent company’s board of directors to
    unilaterally sell the assets of the company for the benefit of its creditors. In effect, the
    Court of Chancery overrode the plain language of Stream Inc.’s charter in favor of a
    common law exception it concluded existed in Delaware and was not superseded by
    Section 271. We also clarified in our Stream TV opinion that the insolvency exception
    identified by the Court of Chancery was superseded by the predecessor statute to Section
    271, if it ever existed in Delaware at all.123
    Daniel’s reliance on Stream TV fails because the Irrevocable Proxy is not plain and
    unambiguous that it runs with the Majority Shares. The Court of Chancery did not ignore
    the plain language of the Irrevocable Proxy in favor of the common law rules in the
    Restatement (Third). Rather, it found that “[i]n the abstract and read in isolation, the phrase
    ‘any act of the Stockholder’ is susceptible to two meanings” and it looked to the
    122
    Id. at 334 (quoting Stream TV Networks, Inc. v. SeeCubic, Inc., 
    250 A.3d 1016
    , 1045 (Del. Ch.
    2020)).
    123
    Id. at 343.
    45
    Restatement (Third) to determine the more “persuasive” reading.124 This is evident by the
    court’s stating that Daniel’s reading of that provision was only “one possible reading,” as
    well as by the various other provisions, including the Addendum, which it found created
    ambiguity. The Court of Chancery’s analysis could have stopped there because under
    Delaware law, ambiguity in an irrevocable proxy is construed against the rights of the
    proxy holder.125 If an irrevocable proxy does not unambiguously provide that it will run
    with the shares in a sale to a subsequent owner, then it does not do so. As the Court of
    Chancery concluded, “the presence of ambiguity alone is sufficient to defeat Daniel’s
    argument.”126
    ii.      The Date of Publication of the Restatement (Third) is Not Dispositive
    Second, Daniel places much weight on the fact that the Restatement (Third) was not
    published until 2006, nine years after the parties drafted and executed the Irrevocable
    Proxy. He argues that as a result, the parties could not possibly have drafted the Irrevocable
    124
    Chancery Opinion, 273 A.3d at 821 (“Read against the backdrop of the default common law
    rules concerning scenarios when irrevocable proxies terminate, given the presence of the
    Addendum, and without any explicit reference in the Non-Termination Provision to a sale of the
    Majority Shares, only Mrs. Hawkins’ reading is persuasive.”); see also Concord Real Estate CDO
    2006-1, Ltd. v. Bank of America N.A., 
    996 A.2d 324
    , 332 (Del. Ch. 2010) (“I look to the common
    law because this body of jurisprudence provides a backdrop of standard default rules that
    supplement negotiated agreements and fill gaps when a contract is incomplete, whether by
    inadvertence or design.”), aff’d, WL 743405 (Del. 2011) (TABLE).
    125
    In other words, it did not need to “confirm” what the “more natural reading” was. See Chancery
    Opinion, 273 A.3d at 819 (“Read in context and against the backdrop of the common law, the more
    natural reading is that the Non-Termination Provision confirms that the Stockholder cannot
    terminate the Irrevocable Proxy while owning the Majority Shares.”).
    126
    Id. at 821.
    46
    Proxy with the default principles articulated in the Restatement (Third).127 This argument
    is unpersuasive for the same reason stated above.
    Because the Restatement (Third) is an articulation of existing common law,128 the
    relevant question is whether at the time the Irrevocable Proxy was executed, Delaware
    common law supported the principle cited in the Restatement (Third). Daniel did not cite
    Delaware case law that establishes his view of the common law in Delaware in 1997 when
    the Irrevocable Proxy was executed. However, we observe that the Court of Chancery
    recognized a principle similar to that stated in comment b several times prior to 1997. In
    1941, the court recognized that “[t]he right to vote shares of corporate stock, having voting
    powers, has always been incident to its legal ownership.129 And in 1993, it stated that
    Delaware law presumes that “in the sale of the underlying stock . . . the seller is contracting
    to sell and assigns all of its rights, title and interest in the stock.”130 Similarly, in 1875, the
    127
    Opening Br. at 24.
    128
    See, e.g., Samson v. Smith, 
    560 A.2d 1024
    , 1027–28 (Del. 1989) (observing that the Restatement
    (Second) of Torts is “merely a formulation of well established common law principles”).
    129
    In re Giant Portland Cement Co., 
    21 A.2d 697
    , 701 (Del. Ch. 1941); see also Giuricich v.
    Emtrol Corp., 
    449 A.2d 232
    , 239 (Del. 1982) (“As a general rule the right to vote shares of
    corporate stock having voting powers at stockholders’ meetings is an incident of their legal and
    record ownership.”) (citing Tracy v. Brentwood Village Corp., 
    59 A.2d 708
    , 709 (Del. Ch. 1948)));
    Norton v. Digital Applications, Inc., 
    305 A.2d 656
    , 659 (Del. Ch. 1973) (“The right to vote shares
    of stock issued by a Delaware corporation is an incident of legal ownership.”).
    130
    Commonwealth Assocs., 
    641 A.2d at 158
    . In considering the validity and enforceability of a
    negotiated provision providing for the retention of a “dangling” right to vote as of the record date
    in a post-record date sale of corporate stock, Chancellor Allen stated that “the legally presumed
    implication, in a sale of the underlying stock, would be that the seller is contracting to sell and
    assign all of its rights, title and interest in the stock, including its right to grant a consent or a
    revocation with respect to a past record date, and that upon request the seller will, in good faith,
    take such ministerial steps as are necessary (e.g., granting proxies) to effectuate that transfer.” 
    Id.
    47
    United States Supreme Court recognized the principle that all rights and obligations follow
    shares in a transfer of stock.131 These cases stand for the general proposition that, when
    legal ownership of stock is transferred, the right to vote such stock is transferred too.
    Although Genger Trial came later, we note that the principle of law articulated in Genger
    Trial requiring an irrevocable proxy to clearly and unambiguously state that it runs with
    shares in a transfer to a third party,132 suggests that the default common law rule is that
    voting rights follow the shares in a stock transfer.
    In any event, we need not resolve the debate about whether the rule provided in
    comment b of the Restatement (Third) — or some other rule as Daniel contends — was
    firmly established common law in Delaware at the time the Irrevocable Proxy was executed
    because the Court of Chancery’s discussion of the Restatement (Third) was not essential
    to its finding that the Irrevocable Proxy does not clearly and unambiguously state that it
    shall run with the Majority Shares. 133 Daniel’s arguments fail because at the most, his
    arguments show only that there are two reasonable ways to read the Non-Termination
    131
    Webster v. Upton, 
    91 U.S. 65
    , 70 (1875) (“When an original subscriber to the stock of an
    incorporated company, who is so bound to pay the instalments on his subscription from time to
    time as they are called in by the company, transfers his stock to another person, such other person
    is substituted not only to the rights, but to the obligations, of the original subscriber, and he is
    bound to pay up the instalments called for after the transfer to him.”) (citing JOSEPH K. ANGELL &
    SAMUEL AMES, Treatise on the Law of Private Corporations § 534 (4th ed. 1852))).
    Genger Trial, 
    2010 WL 2901704
    , at *20 (“Even if the language of the Proxy was ambiguous–
    132
    which it is not–public policy concerns require that the Proxy be strictly construed.”).
    133
    For the same reasons, we need not address Daniel’s third and final argument that the
    Restatement (Second) of Agency § 139 cmt. a (Am. Law Inst. 1958), which was the provision in
    effect when the Irrevocable Proxy was executed, conflicts with comment b, which he contends
    “represented a material change in the default principles.” Opening Br. at 24–25; Reply Br. at 4.
    48
    Provision and, thus, the Irrevocable Proxy is ambiguous.134 For the public policy reasons
    discussed above, a showing of ambiguity requires us to construe the Non-Termination
    Provision narrowly, as the Court of Chancery did below, against the rights of the proxy
    holder.
    b. The Court of Chancery Did Not Err in Concluding that the Language “Any Other
    Event or Events” Does Not Include a Sale of the Majority Shares
    The Non-Termination Provision states that the Stockholder agrees that the proxy
    will not terminate in the specific situations discussed above, “or by the occurrence of any
    other event or events other than as provided in Section 4 hereof.”135 Daniel argues that this
    language serves as a catch-all for acts of the Stockholder and encompasses a sale of the
    Majority Shares.136 The Court of Chancery acknowledged the catch-all nature of this
    language but concluded that it was subject to “at least two interpretations.”137 Moreover,
    it concluded that “against the backdrop of the common law rules, in the presence of the
    Addendum, and in the absence of any reference to a transfer of the Majority Shares,” only
    one reading was reasonable, namely, that the catch-all encompassed only those actions
    taken by the Stockholder while the Stockholder owns the Majority Shares.138 On appeal,
    Daniel argues that the Court of Chancery improperly read the language “while the
    134
    See Cox Commc’ns, Inc. v. T-Mobile US, Inc., 
    273 A.3d 752
    , 760 (Del. 2022) (“Ambiguity is
    present ‘only when the provisions in controversy are reasonably or fairly susceptible of different
    interpretations or may have two or more different meanings.’”) (quoting Rhone-Poulenc Basic
    Chems. Co. v. Am. Motorists Ins. Co., 
    616 A.2d 1192
    , 1196 (Del. 1992))).
    135
    App. to Opening Br. at A035 (Irrevocable Proxy at 2, ¶ 5).
    136
    Opening Br. at 28.
    137
    Chancery Opinion, 273 A.3d at 822.
    138
    Id.
    49
    Stockholder owns the shares” into the Non-Termination Provision and did not give effect
    to the plain meaning of the catch-all language, which would include a sale of the Majority
    Shares as “any other event or events.”139
    First, Daniel’s contends that no Delaware authority requires the use of the word
    “transfer” or “sale” to manifest the parties’ intent for a proxy to run with the shares.140
    However, the Court of Chancery did not hold that, for an irrevocable proxy to run with
    shares, the proxy instrument must use the magic words “transfer” or “sale.” Rather, the
    Court of Chancery held that for an irrevocable proxy to run with shares, the proxy
    instrument must evince the parties’ clear and unambiguous intent for it to do so. In this
    case, the absence of the words “transfer” or “sale” supports the Court of Chancery’s finding
    that the Irrevocable Proxy did not evince such an intent, particularly in the face of how the
    word “transfer” is used elsewhere in the Irrevocable Proxy, the presence of the Addendum,
    and its unchallenged findings as to the Appointment Provision and the definitions of
    “Stockholder” and “Shares.”
    The Court of Chancery also relied on its opinion in Genger Trial,141 which we
    affirmed in relevant part.142 There, the Court of Chancery found that the absence of
    language regarding transferees in the assignment provision indicated the parties did not
    intend for the proxy to follow the shares. The Court of Chancery stated:
    139
    Opening Br. at 28.
    140
    Id. at 29; Reply Br. at 9.
    141
    
    2010 WL 2901704
    .
    Genger, 
    26 A.3d at 198
     (“The Proxy contains no provision that would bind any subsequent
    142
    owner of those shares.”) (emphasis in original).
    50
    If [the proxyholder] wanted to keep the Proxy after a transfer, he could have
    easily inserted clear language–such as “this Proxy shall bind any subsequent
    transferees”–into the Proxy to that effect. He did not, and thus there is no
    reason found in the text of the Proxy to indicate that it is binding upon the
    [subsequent transferee].143
    Daniel does not attempt to distinguish Genger Trial in his briefing on appeal, and the same
    reasoning applies here.
    Further, Daniel reads the Non-Termination Provision in a vacuum, apart from its
    context. Mrs. Hawkins more persuasively considers the Non-Termination Provision in the
    context of the structure of the entire Irrevocable Proxy. The Non-Termination Provision
    begins by saying that “[t]he Stockholder agrees,” meaning Pike.             The recitals and
    Appointment Provision indicate that the Irrevocable Proxy applies only to shares held by
    the Stockholder. Absent the explicit language of a “transfer” or “sale,” a reasonable
    reading of the language “any other event” is that, consistent with the rest of the Non-
    Termination Provision and the Irrevocable Proxy, it only applies to events occurring when
    the Stockholder (Pike and now the Partnership) owns the shares. Daniel’s response that
    “an Irrevocable Proxy always represents a commitment of the stockholder at the time of
    execution since such person is the only one that has the power to grant the authority to the
    proxy holders to vote the shares”144 is unavailing because the definition of “Stockholder”
    only references Pike, and as explained by the Addendum, Old MedApproach or any other
    MedApproach Person who holds any of the Shares or any of the Proxy Shares and agrees
    143
    Genger Trial, 
    2010 WL 2901704
    , at *20.
    144
    Reply Br. at 6.
    51
    to be bound by the Irrevocable Proxy. Again, the Court of Chancery’s unchallenged
    findings as to the significance of the definitions of “Shares” and “Stockholder,” or the
    Appointment Provision, support an alternative reasonable reading of the Irrevocable Proxy,
    and at the very least, render the contract ambiguous.
    We find Daniel’s counterargument that the “provision elsewhere makes clear that
    circumstances in which the Stockholder no longer owns the shares (e.g., the death of the
    Stockholder) will not affect a termination” more persuasive.145 Still, it only rises to the
    level of one possible interpretation of the Non-Termination Provision.             It does not
    overcome the Court of Chancery’s unchallenged findings and unambiguously provide that
    the Irrevocable Proxy shall run with the Majority Shares.
    Finally, Daniel claims that the Court of Chancery erred as a matter of law by relying
    on the existence of the Addendum because the Addendum was a separate agreement apart
    from the Irrevocable Proxy and it “was drafted by Popco and its counsel, not the giver of
    the Irrevocable Proxy.”146 He further argues that even if we were to consider the existence
    of the Addendum, the Addendum was only “belt and suspenders” and did not reflect an
    intent for the Irrevocable Proxy to run with the shares.
    To begin with, the Addendum is best viewed as part of the Irrevocable Proxy and
    not as extrinsic evidence, as Daniel claims.147 The Addendum is on “the face of the
    145
    Opening Br. at 29; Reply Br. at 8–9.
    146
    Opening Br. at 30.
    147
    See Chancery Opinion, 273 A.3d at 811 (“In broad strokes, the Irrevocable Proxy consists of a
    preamble with recitals, fifteen operative provisions, and the Addendum.”).
    52
    contract”148 and is within “its four corners.”149 It is found in a single paragraph on the
    signature page to the Irrevocable Proxy — the same signature page that Pike signed as the
    Stockholder.150 It was also executed on the same day as the Irrevocable Proxy.
    Moreover, other facts undercut Daniel’s argument, including the Court of
    Chancery’s factual finding that Popco saw a need for the Addendum because it did not
    believe the Irrevocable Proxy would otherwise run with the Majority Shares.151 Based on
    the record, the trial court’s findings are not clearly erroneous.
    Finally, we find Daniel’s “belt-and-suspenders” argument unpersuasive because of
    the lack of clear language in the proxy instrument that the Irrevocable Proxy will run with
    the shares and the presence of the Transfer Restriction. A “belt-and-suspenders” reading
    cuts against our preference to avoid redundancy in interpreting contracts. 152                   The
    148
    See Evidence, BLACK’S LAW DICTIONARY (11th ed. 2019) (defining “extrinsic evidence” as
    “[e]vidence relating to a contract but not appearing on the face of the contract because it comes
    from other sources, such as statements between the parties or the circumstances surrounding the
    agreement”).
    149
    See GMG Cap. Invs., LLC v. Athenian Venture P’rs. I, L.P., 
    36 A.3d 776
    , 783 (Del. 2012)
    (observing that, when applied, “the parol evidence rule bars the admission of evidence from
    outside the contract’s four corners to vary or contradict [ ] unambiguous language”).
    150
    App. to Opening Br. at A039–40 (Irrevocable Proxy at 5–6).
    151
    Chancery Opinion, 273 A.3d at 829 (citing W. B. Daniel Trial Testimony at 146–47).
    152
    Compare Osborn, 
    991 A.2d at 1159
     (“‘We will read a contract as a whole and we will give
    each provision and term effect, so as not to render any part of the contract mere surplusage.’ We
    will not read a contract to render a provision or term ‘meaningless or illusory.’”) (first citing Kuhn
    Construction, Inc. v. Diamond State Port Corp., 
    2010 WL 779992
    , at *2 (Del. Mar. 8, 2010); then
    citing Sonitrol Holding Co. v. Marceau Investissements, 
    607 A.2d 1177
    , 1183 (Del. 1992))), with
    Julius v. Accurus Aerospace Corp., 
    2019 WL 5681610
    , at *11 (Del. Ch. Oct. 31, 2019) (“While
    redundancy is sought to be avoided in interpreting contracts, this principle of construction does
    not go so far as to counsel the creation of contract meaning for which there is little or no support
    in order to avoid redundancy.”) (citing U.S. W., Inc. v. Time Warner Inc., 
    1996 WL 307445
    , at *15
    (Del. Ch. June 6, 1996))), aff’d, 
    241 A.3d 220
     (Del. 2020). See also ANTONIN SCALIA & BRYAN
    A. GARNER, Reading Law: The Interpretation of Legal Texts 176 (2012) (“If a provision is
    53
    Addendum does not solely serve to clarify that the Irrevocable Proxy is binding on Old
    MedApproach; it also contains the Transfer Restriction. The Court of Chancery found that
    the Transfer Restriction applies only to MedApproach Persons, as defined in the
    Addendum, but not to unaffiliated third parties.               Daniel does not challenge this
    interpretation on appeal. Thus, the Addendum serves a further purpose, which itself
    demonstrates that the Irrevocable Proxy does not otherwise bind unaffiliated third parties.
    3. The Assignment Provision
    Daniel’s third and final argument on appeal is that the Court of Chancery erred by
    not giving “effect to all of the terms of the Irrevocable Proxy and improperly limiting the
    assignment clause of the Irrevocable Proxy so as not to bind assigns of the Stockholder.”153
    The Assignment Provision, found in paragraph 15 of the Irrevocable Proxy, states in its
    entirety:
    This Irrevocable Proxy and the rights of the Holders under this Irrevocable
    Proxy may not be assigned except that (a) any Holder may, with the consent
    of the remaining Holders, transfer such Holder’s rights to any person who is,
    or is affiliated with, a limited partner of the Partnership, and (b) the Holders
    may act pursuant to this Irrevocable Proxy, in voting the Proxy Shares or
    otherwise, through any duly authorized officer or employee of [Danco GP].
    This Irrevocable Proxy shall be binding upon and inure to the benefit of
    Stockholder and the Holders and their respective heirs, devises, legatees,
    personal representatives, agents and permitted assigns.154
    susceptible of (1) a meaning that gives it an effect already achieved by another provision, or that
    deprives another provision of all independent effect, and (2) another meaning that leaves both
    provisions with some independent operation, the latter should be preferred.”).
    153
    Opening Br. at 3; Reply Br. at 14.
    154
    App. to Opening Br. at A037 (Irrevocable Proxy at 4, ¶ 5).
    54
    The Assignment Provision begins with a blanket prohibition on assignment by the
    Holders in the first sentence (the “No-Assignment Clause”), followed by two exceptions
    to the blanket prohibition in clauses (a) and (b) (the “Holder Exceptions”). The final
    sentence identifies the beneficiaries of the Irrevocable Proxy and those who will be bound
    by the Irrevocable Proxy (the “Bound Parties Clause”).
    Daniel argues that the Bound Parties Clause causes the Irrevocable Proxy to bind
    the Stockholder and his permitted assigns, which includes purchasers of the Majority
    Shares. Rejecting this argument, the Court of Chancery first held that the phrase “permitted
    assigns” does not include purchasers of the Majority Shares. It then held that, even if
    Daniel is correct that the phrase “permitted assigns” included subsequent purchasers, the
    “only reasonable” reading of the Bound Parties Clause is that it binds only the “permitted
    assigns” of the Holders, not those of the Stockholder.155 The Court of Chancery explained
    that this reading was the “only reasonable” one because it applies the rule of the last
    antecedent,156 accords with the “more natural reading” of the sentence, and “better fits the
    155
    Chancery Opinion, 273 A.3d at 825–26.
    156
    The rule of the last antecedent is a canon of construction which provides that:
    Referential and qualifying words and phrases, where no contrary intention appears,
    refer solely to the last antecedent. The last antecedent is the last word, phrase, or
    clause that can be made an antecedent without impairing the meaning of the
    sentence. Thus a proviso usually applies to the provision or clause immediately
    preceding it. A qualifying phrase separated from antecedents by a comma is
    evidence that the qualifier is supposed to apply to all the antecedents instead of only
    to the immediately preceding one.
    2A NORMAN J. SINGER & SHAMBIE SINGER, Sutherland Statutes and Statutory Construction §
    47:33 (7th ed. 2010), available at Westlaw (database updated Nov. 2022) (internal quotation
    marks and footnotes omitted); see also Rubick v. Sec. Instrument Corp., 
    766 A.2d 15
    , 18 (Del.
    2000) (applying the rule that “[r]eferential and qualifying words and phrases, where no contrary
    55
    structure of the Assignment Provision, which starts with the No-Assignment Clause,
    continues with the Holder Exceptions, and finishes with the Bound Parties Clause and its
    specific reference to ‘permitted assigns.’”157
    a. The Court of Chancery Did Not Err in Finding That “Permitted Assigns” Does
    Not Include Transferees
    As a Delaware court, we interpret “contract terms according to their plain, ordinary
    meaning.”158 Daniel argues that the Court of Chancery committed legal error in finding
    that the terms “assigns” and “transferees” “are not equivalent and the Irrevocable Proxy
    needed to use the specific word ‘transferee,’ not ‘assign,’ to bind subsequent owners.”159
    He asserts that, although the Court of Chancery properly looked to the dictionary definition
    of “assignment,” its interpretation of the Bound Parties Clause was “inconsistent with the
    plain dictionary definition of an assignment as encompassing the transfer of property from
    one person to another,” a definition we recognized in Stream TV.160
    We disagree. Although it is true, as we discussed in Stream TV, that an assignment
    may be a “type of transfer or relinquishment of property[;]”161 context matters in
    intention appears, refer solely to the last antecedent”) (quoting 2A NORMAN J. SINGER, Sutherland
    Statutes and Statutory Construction, § 47.33 (6th ed. 2000))).
    157
    Chancery Opinion, 273 A.3d at 825–26.
    158
    Alta Berkeley VI C.V., 
    41 A.3d at 385
    .
    159
    Opening Br. at 34–35.
    160
    Id. at 35 (referencing Stream TV, 279 A.3d at 340–41).
    161
    Stream TV, 279 A.3d at 340. As discussed herein, the question before this Court in Stream TV
    was whether the “transfer and assignment of all rights, title and interest in all of [Stream TV Inc.’s]
    assets” for the benefit of creditors was “a sale, lease, or other disposition” such that it would require
    a majority Class B stockholder vote under Stream TV Inc.’s charter. Id. In interpreting the
    charter’s plain language, we looked to dictionary definitions of “disposition” and “assignment,”
    and read the charter as a whole, particularly looking to the definition of “[t]ransfer” and the usage
    56
    determining which “type” of transfer.162 “[I]t is well established that a court interpreting
    any contractual provision . . . must give effect to all terms of the instrument, must read the
    instrument as a whole, and, if possible, reconcile all the provisions of the instrument.”163
    In the context of the Irrevocable Proxy, Daniel’s plain reading of the term is not nuanced
    enough, particularly given the structure of the Assignment Provision, and how the term
    “transferee” is used elsewhere in the Irrevocable Proxy. His reading overlooks the
    fundamental nature of a proxy as an instrument that divides the economic rights and the
    voting rights that attach to share ownership.
    Comparing dictionary definitions of “transfer,”164 to definitions of “assignee,”165 the
    Court of Chancery found that an “assignee generally does not receive the full bundle of
    of “disposition” therein. From this analysis, we found that “[a]n assignment of all rights, title and
    interest in the assets of the [c]ompany to [another] is a ‘disposition’ because it is a type of transfer
    or relinquishment of property.” Id. (emphasis added). As the Court of Chancery found here, an
    assignment is a narrower term than transfer; it is a type of transfer. Chancery Opinion, 273 A.3d
    at 826 (explaining “[a] transfer is the broader term, and it generally refers to a change involving
    all aspects of ownership” whereas “[a]n assignment is the narrower term, and it generally refers to
    a change involving specific rights”). The Stream Omnibus Agreement provided for a broad type
    of transfer and assignment. By its language it “transferr[ed] and assign[ed] all rights, title and
    interest.” Stream TV, 279 A.3d at 340 (emphasis added). Here, “assigns” is used in a narrower
    sense.
    162
    See Chicago Bridge & Iron Co. N.V. v. Westinghouse Electric Co. LLC, 
    166 A.3d 912
    , 913–14
    (Del. 2017) (“In giving sensible life to a real-world contract, courts must read the specific
    provisions of the contract in light of the entire contract.”); see also SCALIA & GARNER, supra note
    152, at 69 (observing that the ordinary-meaning canon, that “[w]ords are to be understood in their
    ordinary, everyday meanings—unless the context indicates that they bear a technical sense,”
    “governs constitutions, statutes, rules, and private instruments”).
    163
    See Alta Berkeley VI C.V., 
    41 A.3d at
    385–86 (quoting Elliot Assoc., L.P. v. Avatex Corp., 
    715 A.2d 843
    , 854 (Del. 1998)).
    164
    Chancery Opinion, 273 A.3d at 826 (citing Transfer, BLACK’S LAW DICTIONARY (11th ed. 2019)
    (“A conveyance of title or property from one person to another.”).
    165
    Id. (citing Assignee, BLACK’S LAW DICTIONARY (11th ed. 2019) (“Someone to whom property
    rights or powers are transferred by another.”) and RESTATEMENT (SECOND) OF CONTRACTS § 316
    57
    rights associated with the underlying property interest, but rather only a subset of those
    rights.”166      Additional dictionary definitions suggest that an “assignee” is the word
    commonly used for someone who receives a “right” underlying the property interest.167
    Accordingly, the Court of Chancery found that the terms are used differently in
    different contexts.168 The court observed that this difference “is perhaps best reflected in
    our alternative entity statutes, where an effort to transfer an interest in a limited partnership
    or limited liability company results in the recipient becoming an assignee who possesses
    economic rights, but not governance rights.”169 The same is true in contract law, where, as
    the court observed, “the original counterparty remains bound under the contract
    notwithstanding the assignment, unless the new party is substituted through a novation.”170
    Although we agree with the Court of Chancery that “transferee” and “assigns” are
    used differently in different contents, we recognize that the terms can have overlapping
    meanings.171 Resolution here hinges on whether the terms were used differently in this
    (Am. Law. Inst. 1981), available at Westlaw (database updated Oct. 2022) (defining
    “[a]ssignment” as “the transfer of a right by the owner (the oblige or assignor) to another person
    (the assignee)”)).
    166
    Id.
    167
    Assignee, MERRIAM-WEBSTER, https://www.merriam-webster.com/dictionary/assignee (last
    visited Dec. 21, 2022) (“[A] person to whom a right or property is transferred.”).
    168
    See SCALIA & GARNER, supra note 152, at 70 (observing that most common English words
    have more than one ordinary meaning and stating that “[o]ne should assume the contextually
    appropriate ordinary meaning unless there is reason to think otherwise”).
    169
    Chancery Opinion, 273 A.3d at 826–27 (citing 6 Del. C. § 17-702(a)).
    170
    Id. at 827 (citing Schwartz v. Centennial Ins. Co., 
    1980 WL 77940
    , at *2 (Del. Ch. Jan. 16,
    1980) and P.C. Connection, Inc. v. Synygy Ltd., 
    2021 WL 57016
    , at *14 (Del. Ch. Jan. 7, 2021)).
    171
    See Transferee, MERRIAM-WEBSTER, https://www.merriam-webster.com/dictionary/transferee
    (last visited Dec. 21, 2022) (“[A] person to whom something is transferred or conveyed.”).
    58
    context.172 The structure of the Assignment Provision along with the divergent uses of the
    terms elsewhere in the Irrevocable Proxy support the Court of Chancery’s conclusion that
    they were used differently here, and that the term “permitted assigns” does not include
    transferees.
    The word “assigns” in the Assignment Provision takes on a different meaning than
    the word “transferee” does in the Addendum. Their respective uses are consistent with the
    Court of Chancery’s determination that, in the Irrevocable Proxy, an assignee is one who
    receives only a subset of property rights, whereas a transferee is one who receives all
    property rights associated with the underlying property interest.              In the Assignment
    Provision, “permitted assigns” are those who have been assigned the “Irrevocable Proxy”
    or the “rights of the Holders.” The Assignment Provision is structured as a prohibition on
    the assignment of “the rights of the Holders,” followed by two exceptions. The first
    exception allows a Holder who has the consent of the other Holders to “transfer such
    Holder’s rights” to “any person affiliated with a limited partner of the Partnership.” The
    second exception allows a Holder “in voting the Proxy Shares or otherwise” to do so
    through a duly authorized officer or employee of Danco GP.
    On the other hand, “transferee” is used in the Addendum to refer to someone who
    has been transferred legal ownership of the shares, rather than only the underlying voting
    172
    Lorillard Tobacco v. Am. Legacy Found., 
    903 A.2d 728
    , 740 (Del. 2006) (“There may be more
    than one dictionary definition, and parties may disagree on the meaning of the definition as applied
    to their case, but if merely applying a definition in the dictionary suffices to create ambiguity, no
    term would be unambiguous. A court must accept and apply the plain meaning of an unambiguous
    term in the context of the contract language and circumstances, insofar as the parties themselves
    would have agreed ex ante.”) (internal quotation marks and footnotes omitted)).
    59
    rights. The Addendum documents Old MedApproach’s agreement “not to transfer any
    such shares to any other MedApproach Person unless such transferee agrees in writing
    satisfactory to the [ ] Holders (other than W. Bradley Daniel) to be bound).” 173 The fact
    that the parties could have used “transferee” in the Assignment Provision, as they did
    elsewhere in the Irrevocable Proxy, but chose not to, supports the Court of Chancery’s
    reading as a reasonable one.
    The Court of Chancery also relied on its decision in Genger Trial with respect to
    transferee language, discussed above. Daniel argues that no Delaware court has held that
    the drafters of an irrevocable proxy need to use the magic word “transferee” for the
    irrevocable proxy to run with the shares and be binding on a subsequent owner.174 But the
    Court of Chancery did not require the use of the word “transferee” for an irrevocable proxy
    to be binding. Rather, it found that the absence of the words “transferee,” “transfer,” or
    “sale,” in the context of the plain language of the Irrevocable Proxy, indicated that the
    instrument was not intended to run with a transfer of the underlying shares. Here, the
    language of the Assignment Provision does not clearly provide that the Irrevocable Proxy
    will run with the shares. In sum, considering that the fundamental nature of an irrevocable
    proxy involves a division of property rights, the structure of the Assignment Provision, and
    the divergent uses of the terms in the Irrevocable Proxy, the Court of Chancery’s finding
    that permitted assigns does not include transferees was not legal error.
    173
    App. to Opening Br. at A039 (Irrevocable Proxy at 5).
    174
    Opening Br. at 35–36.
    60
    b. Nor does the Bound Parties Clause Provide that the Irrevocable Proxy Runs with
    the Majority Shares
    Even if Daniel is right that the term “assigns” includes “transferees” in this case, his
    reliance on the Assignment Provision fails because the term “permitted assigns” does not
    clearly apply to those of the Stockholder. The Court of Chancery found that the plain
    language of the sentence was ambiguous as to whether it bound permitted assigns of the
    Stockholder in addition to those of the Holders. It then looked to the structure of the
    provision and applied the rule of the last antecedent and grammatical canons to conclude
    that the Bound Parties Clause only binds permitted assigns of the Holders, not those of the
    Stockholder.
    The rule of the last antecedent is a settled principle of interpretation.175 It provides
    that “referential and qualifying words and phrases, where no contrary intention appears,
    refer solely to the last antecedent.”176 Read according to the rule, the adjective “their” in
    the Bound Parties Clause modifies the only the nearest antecedent: “the Holders.”
    Therefore, only the permitted assigns of the Holders are bound, not the permitted assigns
    of the Stockholder.
    On appeal, Daniel argues that reliance on the rule of the last antecedent was legal
    error because application of the rule here, “violate[s] [the] cardinal principle” that courts
    175
    See, e.g., Rag Am. Coal Co. v. AEI Res., Inc., 
    1999 WL 1261376
    , at *4 (Del. Ch. Dec. 7, 1999)
    (observing that ordinarily, qualifying words or phrases, where no contrary intention appears,
    usually relate to the last antecedent) (internal quotation marks omitted).
    176
    Rubick, 
    766 A.2d at 18
     (quoting SINGER, supra note 156).
    61
    are “to give effect to all terms of the instrument.”177 According to Daniel, the Stockholder
    is already bound by the Irrevocable Proxy so if the adjective “their” does not reach back
    through “Holders” to modify “Stockholder” then the word “Stockholder” serves no purpose
    in the sentence. It becomes surplusage.
    The Court of Chancery acknowledged that Daniel’s reading is reasonable, but it
    concluded that the Bound Parties Clause is ambiguous. It noted that the placement of an
    adjective often creates ambiguity.178 Here, the ambiguity is compounded by the omission
    of an Oxford comma.179 The Court of Chancery reconstructed the Bound Parties Clause,
    this time eliminating an “and” and placing an Oxford comma:
    If “their” applied to both “Stockholder” and “the Holders,” then the natural
    way to write the sentence would be to say that “[t]his Irrevocable Proxy shall
    be binding upon and inure to the benefit of Stockholder, the Holders, and
    their respective heirs, devises, legatees, personal representatives, agents and
    permitted assigns.”180
    If the drafters of the Irrevocable Proxy had written the Bound Parties Clause as laid
    out above, Daniel’s reading would be the most natural one. But they did not do so. Daniel
    argues that “[a] court applying Delaware law will not allow the imprecise placement of
    177
    Opening Br. at 33–34 (citing Elliot Assocs., 
    715 A.2d at 854
    ).
    178
    Chancery Opinion, 273 A.3d at 825.
    179
    An Oxford comma (aka a serial comma or Harvard comma) is a comma that separates the last
    from the next-to-last item in a list of more than two. It normally follows a conjunction. See BRYAN
    A. GARNER, Garner’s Modern English Usage 897, 981 (5th ed. 2022)).
    180
    Chancery Opinion, 273 A.3d at 825–26. Accord GARNER, supra note 179, at 982, 985.
    Garner explains that proponents of the Oxford comma “point out that including it never creates
    an ambiguity, whereas omitting it fairly often does.” GARNER, supra note 179, at 982. In line
    with the weight of authority, Garner himself favors a bright line rule of including an Oxford
    comma to ensure consistency and clarity. GARNER, supra note 179, at 985.
    62
    adverbs and commas to alter the otherwise plain meaning of a contractual provision or to
    frustrate the overall plan or scheme memorialized in the parties’ contract.”181 But the Court
    of Chancery’s reasoning for applying the rule of the last antecedent and other grammatical
    canons was precisely because the provision was ambiguous.182
    Mrs. Hawkins interpretation also fits better with the grammatical rule of pronoun-
    antecedent agreement. The plural possessive “their” agrees with the plural antecedent “the
    Holders,” not the singular antecedent “Stockholder.”183 Moreover, it brings the Bound
    Parties Clause into compliance with the grammatical rules governing determiners.184
    181
    Reply Br. at 15 (citing Symbiont.iO, Inc. v. Ipreo Hldgs., LLC, 
    2021 WL 3575709
    , at *35 (Del
    Ch. Aug. 13, 2021) (internal quotation marks omitted)). Accord E.I. du Pont de Nemours & Co.
    v. Green, 
    411 A.2d 953
    , 956 (Del. 1980) (“[T]he [last antecedent] rule has its limitations, as stated
    in 2A Sutherland, Statutes and Statutory Constructions, § 47.33 (4th [e]d. 1973), ‘When the sense
    of the entire act requires that a qualifying word or phrase apply to several preceding or succeeding
    sections, the word or phrase will not be restricted to its immediate antecedent.’”) (emphasis
    added)); MicroStrategy Inc. v. Acacia Research Corp., 
    2010 WL 5550455
    , at *7 (Del. Ch. Dec.
    30, 2010) (“In reaching that conclusion, I am mindful that grammar and punctuation are of
    secondary importance to a court in interpreting a contract where such grammar and punctuation
    reasonably would frustrate the parties’ clear intent as evinced from the language used in the
    contract. Indeed, a court should ‘not allow the imprecise placement of adverbs and commas to
    alter the otherwise plain meaning of a contractual provision or to frustrate the overall plan or
    scheme memorialized in the parties’ contract.’”) (citing Interim Healthcare, Inc. v. Spherion
    Corp., 
    884 A.2d 513
    , 555–56 (Del. Super. 2005), aff’d, 
    886 A.2d 1278
     (Del. 2005))); Facebook,
    Inc. v. Duguid, 
    141 S. Ct. 1163
    , 1170 n.5 (2021) (“Linguistic canons are tools of statutory
    interpretation whose usefulness depends on the particular statutory text and context at issue.”); see
    also Barnhart v. Thomas, 
    540 U.S. 20
    , 26 (2003) (observing that the rule is “not absolute” and can
    be “overcome by other indicia of meaning”).
    182
    Chancery Opinion, 273 A.3d at 825, 828; see also Stream TV, 279 A.3d at 341, 341 n.99
    (collecting cases standing for the proposition that if a contractual provision is unambiguous, the
    court need not interpret it and the language of the provision itself controls).
    183
    See GARNER, supra note 179, at 239 (“[A] relative pronoun is supposed to agree with its
    antecedent in both number and person.”). But cf. GARNER, supra note 179, at 239 (recognizing
    that the matching of “they” with a singular noun is now a common way to avoid sexist or gendered
    language).
    184
    A determiner is “[a] type of adjective that limits how a noun element applies.” GARNER, supra
    note 179, at 1204. Examples of determiners “are articles (a, an, and the), demonstrative adjectives
    63
    Those rules state that “[w]ith postpositive modifiers, the insertion of a determiner before
    the second item tends to cut off the modifying phrase so that its backward reach is
    limited.”185 Here, the second item is “Holders” and the determiner is “the,” which cuts off
    the modifying phrase “their” from reaching back to modify “Stockholder.”
    Finally, Daniel’s reading is inconsistent with the structure of the Assignment
    Provision. As discussed above, the Assignment Provision is a prohibition on the rights of
    the Holders. It provides for two exceptions. Both only apply to the Holders because only
    the Holders are prohibited from assigning their rights. In a provision addressing a
    prohibition on the Holders’ ability to assign their rights, the most natural reading is that
    “permitted assigns” refers to those assigns permitted by the Holders under the exceptions
    provided for in the previous sentence.
    IV.    CONCLUSION
    For the foregoing reasons, we hold that the Irrevocable Proxy does not run with the
    Majority Shares. Delaware law requires that the irrevocable proxy instrument clearly and
    unambiguously state that such proxy will continue with the shares upon their sale or
    transfer. The Irrevocable Proxy does not do so. Accordingly, we AFFIRM the judgment
    of the Court of Chancery.
    (this, that, these, and those), and indefinite adjectives (e.g., all, any, each, every, some, few).”
    GARNER, supra note 179, at 1204.
    185
    SCALIA & GARNER, supra note 152, at 149 (acknowledging that the effect of a determiner in
    these instances is “not entirely clear” and that a competent drafter will position it earlier in the
    phrase).
    64