Tarpon Bay Partners LLC v. Zerez Holdings Corporation ( 2023 )


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  • 21-1916-cv (L)
    Tarpon Bay Partners LLC v. Zerez Holdings Corporation
    In the
    United States Court of Appeals
    For the Second Circuit
    August Term, 2022
    Nos. 21-1916-cv, 21-2010-cv
    TARPON BAY PARTNERS LLC,
    Plaintiff–Consolidated Defendant–Counterclaim Defendant–Appellant–
    Cross-Appellee,
    STEPHEN M. HICKS,
    SOUTHRIDGE ADVISORS II, LLC, a Delaware limited liability company,
    Consolidated Defendants–Counterclaim Defendants–Appellants–
    Cross-Appellees,
    v.
    ZEREZ HOLDINGS CORPORATION, an Oklahoma corporation, FKA
    DEFINITIVE REST MATTRESS COMPANY,
    Defendant–Consolidated Plaintiff–Counterclaim Plaintiff–Appellee–
    Cross-Appellant,
    DOES, 1–25,
    Consolidated Defendants–Counterclaim Defendants–Appellees. *
    Appeal from the United States District Court
    for the District of Connecticut
    ARGUED: MARCH 3, 2023
    DECIDED: AUGUST 11, 2023
    *  The Clerk of Court is respectfully directed to amend the caption
    accordingly.
    Before: NARDINI, MERRIAM, Circuit Judges, and KATZMANN, 1 Judge.
    Plaintiff-Appellant Tarpon Bay Partners LLC (“Tarpon Bay”)
    and Defendant-Appellee Zerez Holdings Corporation (“Zerez”)
    attempted to reach an investment deal in which Tarpon Bay would
    purchase Zerez’s debt obligations and, in return, receive stock in
    Zerez pursuant to section 3(a)(10) of the Securities Act of 1933. As
    part of this attempt, Zerez issued a promissory note that allowed
    Tarpon Bay to convert $25,000—the signing fee for the attempted
    transaction—into Zerez’s common stock at a 50 percent discount in
    stock price. After the deal broke down, Tarpon Bay demanded more
    than 278 million shares worth nearly $2.23 million on the date of
    conversion. Zerez refused to issue the shares.
    Tarpon Bay sued Zerez to enforce the note, and Zerez
    countersued Tarpon Bay, Southridge Advisors II, and Stephen Hicks
    (together, “Counterclaim Defendants”). On Tarpon Bay’s motion for
    summary judgment, the United States District Court for the District
    of Connecticut (Underhill, J.) held that although genuine issues of
    material fact remained as to whether the note lacked consideration,
    the note was unconscionable as a matter of law and therefore
    unenforceable. On Zerez’s later motion for summary judgment on its
    counterclaims, the district court held in relevant part that Zerez was
    not entitled to relief under the Connecticut Unfair Trade Practices Act
    (“CUTPA”). Tarpon Bay appeals and Zerez cross-appeals from the
    final judgment.
    We first vacate the district court’s holding that the note was
    unconscionable as a matter of law on the record before it at summary
    judgment. We next conclude the district court correctly determined
    that genuine issues of material fact remained as to whether
    1  Judge Gary S. Katzmann, of the United States Court of International
    Trade, sitting by designation.
    2
    consideration supported the note. Finally, we affirm the district
    court’s grant of summary judgment for the Counterclaim Defendants
    on CUTPA on the alternative ground that CUTPA does not apply to
    the case at bar. We VACATE in part, AFFIRM in part, and REMAND
    for further proceedings consistent with this opinion.
    GEORGE O. RICHARDSON, III, Sullivan &
    Worcester LLP, New York, NY, for Plaintiff–
    Appellant and Counterclaim Defendants–
    Appellants.
    JONATHAN M. SHAPIRO, (Evan K.
    Buchberger, on the brief), Aeton Law
    Partners, Middletown, CT, for Defendant–
    Cross-Appellant.
    GARY S. KATZMANN, Judge:
    Before us are the appeal of Plaintiff-Appellant Tarpon Bay
    Partners LLC (“Tarpon Bay”) and cross-appeal of Defendant-
    Appellee Zerez Holdings Corporation (“Zerez”) from the Judgment
    of the United States District Court for the District of Connecticut.
    Tarpon Bay and Zerez are commercial parties who regularly transact
    in the capital markets and attempted to reach an arm’s-length
    investment deal. After the deal broke down, Tarpon Bay sued to
    3
    enforce an allegedly valid promissory note issued by Zerez (the
    “Signing Fee Note”).    Among other defenses and counterclaims,
    Zerez raised the defense of unconscionability and counterclaimed
    that Tarpon Bay, Southridge Advisors II, LLC (“Southridge”), and
    Stephen M. Hicks (“Hicks”) (together, “Counterclaim Defendants”)
    had violated the Connecticut Unfair Trade Practices Act (“CUTPA”),
    
    Conn. Gen. Stat. §§ 42
    -110a to -110q.
    In September 2019, the district court denied summary
    judgment for Tarpon Bay on its enforcement claims because genuine
    issues of material fact remained as to whether the Signing Fee Note
    was supported by consideration. It then held in the same opinion that
    the   Signing   Fee   Note   was       unconscionable   and   therefore
    unenforceable. Tarpon Bay challenges these two holdings on appeal.
    In July 2021, the district court granted summary judgment for Tarpon
    Bay on Zerez’s CUTPA counterclaim, which Zerez challenges on
    4
    cross-appeal.
    We first hold that the record at the summary judgment stage
    did not establish that the Signing Fee Note was unconscionable under
    Connecticut law. We next hold that the district court correctly denied
    summary judgment for Tarpon Bay on its enforcement claims.
    Finally, we hold that the district court’s grant of summary judgment
    on Zerez’s CUTPA claim was warranted on the alternative grounds
    that CUTPA does not apply to the case at bar. Accordingly, we
    VACATE in part, AFFIRM in part, and REMAND for further
    proceedings consistent with this opinion.
    I.    Background
    A.    Factual Background
    Unless otherwise stated, the parties do not dispute the
    following facts. Zerez and Tarpon Bay are sophisticated commercial
    parties who are routine players in the capital markets. Zerez is a
    publicly traded holding company, formed in Oklahoma and operated
    out of California, that invests in and manages emerging technology
    5
    businesses. Joint App’x at 867, 915, 1149. Trading at fractions of a
    cent, Zerez’s common stock is a penny stock listed on the over-the-
    counter (“OTC”) market under the stock symbol “SCNA.” 2 
    Id. at 867, 870
    . Tarpon Bay is a Florida limited liability company managed by
    Southridge, an investment advisory firm based in Connecticut and
    headed by Hicks. 
    Id.
     at 867–68, 874.
    In January 2016, Zerez sought new capital to fund its continued
    2   OTC “securities are securities not listed on a national securities
    exchange.”            Over-the-Counter        (OTC)      Securities,   Investor.gov,
    https://www.investor.gov/introduction-investing/investing-basics/glossary/over-
    counter-otc-securities (last visited Aug. 10, 2023). And microcap stocks,
    commonly referred to as “penny stocks,” refer to shares in “companies with low
    or micro market capitalizations. . . . of less than $250 or $300 million.” Microcap
    Stock, Investor.gov, https://www.investor.gov/introduction-investing/investing-
    basics/glossary/microcap-stock (last visited Aug. 10, 2023).
    Due to the very low price, and to the lack of disclosure requirements that
    are generally applicable to securities listed on national exchanges, penny stocks on
    the OTC market are typically highly volatile in price and generally illiquid. See
    Joshua T. White, U.S. SEC, Outcomes of Investing in OTC Stocks 8–9 (Dec. 16, 2016),
    https://www.sec.gov/files/White_OutcomesOTCinvesting.pdf. Because it can be
    difficult to find a buyer, parties holding penny stock often cannot sell shares
    quickly without lowering the price.
    As of August 10, 2023, SCNA trades at $0.0007 per share. See SCNA,
    OTCMarkets, https://www.otcmarkets.com/stock/SCNA/overview (last visited
    Aug. 10, 2023). Zerez changed its name to “Smart Cannabis Corp.” in September
    2017. See Joint App’x at 972.
    6
    operations and growth. 
    Id. at 1150
    . The company had more than
    $500,000 of debt on its books, so it entertained offers from fundraising
    brokers to provide or procure new capital in exchange for stock or
    other debt. 
    Id.
     Juan Carlos Murga, Zerez’s then-CEO, was in contact
    with individuals from several venture capital and investment funds
    but ultimately proceeded with Anish Aswani of Southridge. 3 
    Id.
     at
    1149–51. The parties dispute how they were initially put in touch. 4
    However it happened, Aswani and Murga engaged in discussions
    that Tarpon Bay would purchase Zerez’s debt obligations and, in
    exchange, receive a commensurate amount of stock in Zerez. 
    Id.
     at
    915–16, 1296. The transaction would reduce Zerez’s carried debt and
    make the company more attractive for future lenders or investors. 
    Id. at 916, 1296
    . Because Zerez would need to issue equity in exchange
    3   Aswani was an employee who negotiated with Zerez on behalf of
    Southridge and Tarpon Bay. 
    Id. at 928
    .
    4 Tarpon Bay alleges that they connected “through a third party familiar
    with both companies that had recommended to Zerez that Tarpon might be able
    to assist Zerez in reducing its carried debt.” 
    Id. at 916
    . Zerez denies the
    involvement of a third party and insists that Aswani placed a “cold call” to Murga.
    
    Id. at 1302
    .
    7
    for its outstanding debt, the parties were aware that the transaction
    would require a court order approving the fairness of the terms
    pursuant to section 3(a)(10) of the Securities Act of 1933. 5 Joint App’x
    at 915–16, 1296.
    Aswani sent Murga a proposed term sheet outlining the key
    aspects of the deal (the “Term Sheet”). 
    Id. at 916, 1296
    . Under the
    Term Sheet, Tarpon Bay would individually engage and execute
    agreements with Zerez’s creditors to buy the debt; Tarpon Bay would
    seek court approval of the section 3(a)(10) transaction within five days
    5 Section 3(a)(10) of the Securities Act exempts issuers from registration for
    securities issued in exchange for outstanding securities or other qualifying value.
    Specifically, the provision exempts from registration:
    [A]ny security which is issued in exchange for one or more bona
    fide outstanding securities, claims or property interests, or partly in
    such exchange and partly for cash, where the terms and conditions
    of such issuance and exchange are approved, after a hearing upon
    the fairness of such terms and conditions at which all persons to
    whom it is proposed to issue securities in such exchange shall have
    the right to appear, by any court, or by any official or agency of the
    United States, or by any State or Territorial banking or insurance
    commission or other governmental authority expressly authorized
    by law to grant such approval . . . .
    15 U.S.C. § 77c(a)(10).
    8
    of executing the agreements with Zerez’s creditors; and Zerez would
    issue a commensurate amount of stock to Tarpon Bay, subject to
    certain limitations not relevant here. Id. at 981–82. The Term Sheet
    also specified that Tarpon Bay would receive (1) a $25,000 fee payable
    in cash or a promissory note for stock at Tarpon Bay’s election
    (“Signing Fee”) and (2) a fee worth $75,000 at minimum upon judicial
    approval of the transaction. Id. at 983. But the signature page of the
    Term Sheet indicated that the Term Sheet “merely represent[s]
    proposed terms for possible liabilities satisfaction. Until definitive
    documentation is executed by all parties, there shall not exist any
    binding obligation,” other than two provisions relating to
    confidentiality and exclusivity. Id. at 984. Murga was personally
    involved in the discussions with Aswani, but Zerez alleges that it
    played no role in drafting the Term Sheet. Id. at 917, 1297, 1303. Zerez
    signed the Term Sheet on January 15, 2016. Id. at 984.
    On January 27, 2016, Zerez executed a convertible promissory
    9
    note to Tarpon Bay for the Signing Fee (“Signing Fee Note”). Id. at
    1005, 1012. The Signing Fee Note was issued pursuant to the Signing
    Fee provision in the Term Sheet. Id. at 917–18, 1296–98. Crucially, the
    Signing Fee Note was payable on demand and allowed Tarpon Bay
    “to convert all . . . of the Outstanding Principal Amount . . . into
    Common Stock at a conversion price . . . for each share of Common
    Stock at a 50% discount from the lowest closing bid price in the 30
    trading days prior to the day that [Tarpon Bay] requests conversion.”
    Id. at 1005–06. The Signing Fee Note also obligated Zerez “to reserve
    at least Five hundred million (500,000,000) shares of its Common
    Stock for issuance to Holder in connection with conversion of this
    Note.” Id. at 1011. Aswani told Murga that Zerez was issuing the
    Signing Fee Note solely for the services that Southridge and Tarpon
    Bay would provide as part of the section 3(a)(10) transaction, and that
    Murga would need to execute the Signing Fee Note to proceed
    because it was a prerequisite to entering into a definitive agreement.
    10
    Id. at 918, 1304. Zerez alleges that it played no role in drafting the
    Signing Fee Note and that it felt that it had no meaningful choice in
    negotiating its terms given its financial condition. Id. at 1304. One
    day after Zerez executed the Signing Fee Note, Hicks signed the Term
    Sheet on January 28, 2016. Id. at 984. Murga alleges that he was
    unaware of Hicks’s involvement prior to that point. Because Hicks
    had been the subject of unrelated lawsuits filed by federal and state
    securities regulators, Murga further alleges that Zerez would not have
    agreed to move forward with Tarpon Bay and Southridge had it
    known that Hicks was involved. Id. at 1151–52.
    Between February and April 2016, Tarpon Bay proceeded to
    reach out to Zerez’s creditors and ultimately executed agreements,
    termed “Claim Purchase Agreements,” with eight creditors to
    purchase a total of $512,874.06 of Zerez’s debt. Id. at 428, 919. Zerez
    has not disputed that it was aware of this process; two of Zerez’s
    largest creditors, whom Tarpon Bay had engaged with Claim
    11
    Purchase Agreements, were Murga himself and Claudia Lima
    (Zerez’s Secretary and Treasurer). Id. at 428, 919, 1000. On June 13,
    2016—more than five days after the last Claim Purchase Agreement
    was executed, which was the time period expressly required by the
    Term Sheet 6 —Tarpon Bay filed an action against Zerez in Florida
    state court seeking a fairness hearing to approve the securities
    transaction pursuant to section 3(a)(10) of the Securities Act. See
    Tarpon Bay Partners, LLC v. Zerez Holdings, No. 2016-CA-001300 (Fla.
    Cir. Ct. filed June 13, 2016); see also Joint App’x at 920–21, 1299.
    But the section 3(a)(10) transaction was never approved. Zerez
    did not appear at the hearing, and the parties dispute why. 7 Id. at 921,
    6  Moreover, the Claim Purchase Agreements required that Tarpon Bay file
    the section 3(a)(10) lawsuit within ten business days of execution. See, e.g., id. at
    1016. The latest Claim Purchase Agreement was executed on April 26, 2016. Id. at
    1063. While the Claim Purchase Agreements were binding on Tarpon Bay, Zerez
    was not a party to those agreements, and the agreements made clear that there
    were no third-party beneficiaries. See, e.g., id. at 1020.
    7 Tarpon Bay asserts that Murga confirmed via email that Zerez had
    obtained counsel to accept service of the section 3(a)(10) complaint but that Tarpon
    Bay never received the contact information of that attorney. Joint App’x at 921.
    Zerez counters that it was never told to retain counsel or pay the attorney’s fee in
    12
    1299. On September 22, 2016, Murga emailed Aswani stating that
    Zerez wished to “stop and cancel the [3(a)(10)] filing” and to “pull
    back on the filing.” Id. at 1067. The next day, Tarpon Bay was
    informed that three creditors were exercising their undisputed rights
    to cancel the Claim Purchase Agreements. 8 Id. at 1178–79.                       On
    October 10, 2016, Zerez sent a letter to Tarpon Bay on official
    letterhead informing Tarpon Bay that Zerez “HEREBY rescinds and
    cancels any and all consulting and/or services relationships with
    Southridge and/or Tarpon Bay . . . , and further HEREBY rescinds and
    cancels the $25,000” Signing Fee Note, citing the lack of “sufficient,
    adequate, []or material services” rendered to Zerez.                  Id. at 1069.
    Tarpon Bay responded via letter on October 17, 2016, asserting that
    Zerez had “no grounds to rescind” the Signing Fee Note and
    the Florida proceeding, and that it was never notified once litigation was filed. Id.
    at 1305, 1665. Zerez maintains that Murga followed up repeatedly with Tarpon
    Bay, and in a call from Murga to Aswani about the transaction’s progress, Aswani
    stated that the transaction was imminent. Id. at 1665.
    8 The Claim Purchase Agreements allowed either party to terminate the
    agreement if the section 3(a)(10) transaction was not approved within ninety days
    of the date of execution. See, e.g., id. at 1017.
    13
    demanding “immediate payment of all principal and interest due
    under the Note.” Id. at 1071–72 (emphasis removed). Zerez also
    changed control and management by the end of October 2016 after it
    had acquired a new principal subsidiary, Next Generation Farming
    Inc. Id. at 945.
    On November 29, 2016, Tarpon Bay sent Zerez a “Notice of
    Conversion” that demanded 278,958,900 shares of Zerez stock worth
    nearly $2.23 million on the date of conversion. Id. at 1074–76. Tarpon
    Bay relied on the Signing Fee Note provision that allowed payment
    in stock, rather than in cash; the cash value at the time, with accrued
    interest and fees, was $27,895.89. Id. at 1005–06, 1075. Tarpon Bay
    took advantage of very low stock pricing in the thirty days before
    November 29, 2016—specifically, the stock price of $0.0002 on
    October 17, 2016—and demanded conversion at the 50 percent
    discounted price per share of $0.0001 pursuant to the Signing Fee
    Note’s conversion formula. Id. at 1075. Hicks candidly stated in later
    14
    deposition testimony that Tarpon Bay timed the conversion to take
    advantage of a price dip: “[W]e wanted to get the lowest possible
    conversion price, receive the shares and sell them in the market at the
    highest possible price. If we waited too long with the stock moving
    up, we would lose the low prices.” Id. at 1228. Tarpon Bay’s request
    for 278,958,900 shares was approximately 55.6 percent of the
    500,000,000 reserve shares that the Signing Fee Note had required
    Zerez to set aside for potential conversion. See id. at 1011. Zerez
    refused to issue the shares to Tarpon Bay, and this litigation ensued.
    B.     Procedural History
    In January 2017, Zerez sued Counterclaim Defendants in the
    U.S. District Court for the Eastern District of California for a
    “judgment enforcing its rescission of the Term Sheet and Note for
    failure of consideration” and damages for unjust enrichment and
    fraud. See Compl. at 7, Zerez Holdings Corp. v. Tarpon Bay Partners LLC,
    No. 2:17CV00029(TLN)(DB) (E.D. Cal. filed Jan. 6, 2017); Joint App’x
    at 157–65. Tarpon Bay separately sued Zerez in Connecticut Superior
    15
    Court in March 2017 seeking specific performance of the conversion
    pursuant to the Signing Fee Note and Term Sheet. See Compl. at 11–
    12, Tarpon Bay Partners LLC v. Zerez Holdings Corp., No. DBD-CV17-
    6021890-S (Conn. Super. Ct. filed Mar. 3, 2017); Joint App’x at 38–39.
    Zerez successfully removed the Connecticut action to the U.S. District
    Court for the District of Connecticut in April 2017. Joint App’x at 20.
    The California case was transferred to the District of Connecticut in
    January 2018, see Zerez Holdings Corp. v. Tarpon Bay Partners LLC, No.
    2:17CV00029(TLN)(DB), 
    2018 WL 402238
     (E.D. Cal. Jan. 12, 2018), and
    the two cases were consolidated into the case from which this appeal
    was taken, Joint App’x at 10.
    In June 2018, Tarpon Bay filed the Amended Complaint seeking
    (1) immediate delivery of the 278,958,900 shares, (2) declaratory
    judgment in its favor, and (3) damages in the amount of $25.9 million
    (together, the “Affirmative Claims”). 
    Id.
     at 842–43. Zerez filed the
    16
    Answer in August 2018 and asserted twelve affirmative defenses 9 and
    eleven counterclaims against Counterclaim Defendants. 10 
    Id.
     at 865–
    66, 882–890.      Notable to this appeal, Zerez’s second affirmative
    defense alleged that the terms of the Signing Fee Note were
    “unconscionable and/or unenforceable.” 
    Id. at 865
    .
    Tarpon Bay moved for summary judgment in January 2019 on
    the Affirmative Claims and Zerez’s twelve affirmative defenses, and
    Counterclaim Defendants moved for summary judgment on all
    eleven of Zerez’s counterclaims. 
    Id. at 911
    . Zerez did not cross-move
    9  Zerez asserted the following affirmative defenses: (1) failure to state a
    claim; (2) unconscionability; (3) lack of consideration; (4) unclean hands; (5)
    estoppel; (6) failure to satisfy the conditions precedent of the Signing Fee Note; (7)
    waiver; (8) laches; (9) rescission of the contract; (10) unjust enrichment; (11)
    voidness for misrepresentations made by Plaintiff; and (12) bad faith. 
    Id.
     at 865–
    66.
    10 Zerez alleged the following counterclaims: (1) Breach of implied contract,
    against Tarpon Bay; (2) Declaratory relief, against Tarpon Bay; (3) Breach of
    fiduciary duty, against Southridge; (4) Usury, against Tarpon Bay; (5) Rescission
    for failure of consideration, against Tarpon Bay; (6) Fraudulent inducement,
    against Counterclaim Defendants; (7) Mistake, against Counterclaim Defendants;
    (8) Aiding and abetting, against Counterclaim Defendants; (9) Civil conspiracy,
    against Counterclaim Defendants; (10) Violation of the California Unfair
    Competition Law, 
    Cal. Bus. & Prof. Code §§ 17200
    –17210, against Counterclaim
    Defendants; and (11) Violation of CUTPA, 
    Conn. Gen. Stat. §§ 42
    -110a to -110q,
    against Counterclaim Defendants. Joint App’x at 882–90.
    17
    for summary judgment and argued only that Tarpon Bay’s motion for
    summary judgment should be denied; regarding the Affirmative
    Claims, Zerez argued that its affirmative defenses precluded
    summary judgment in favor of Tarpon Bay.            
    Id. at 1120
    .   On
    unconscionability, Zerez submitted that, “[a]t a minimum, issues of
    fact remain as to whether the Note was unconscionable including a
    determination of whether the circumstances give rise to terms that are
    so one-sided as to be unconscionable.” 
    Id. at 1123
    . The motions for
    summary judgment were resolved in two decisions: one in September
    2019 on the Affirmative Claims and unconscionability, Tarpon Bay
    Partners LLC v. Zerez Holdings Corp. (Tarpon Bay I), No.
    3:17CV00579(SRU), 
    2019 WL 4646061
     (D. Conn. Sept. 24, 2019), and
    another in July 2021 on all eleven of Zerez’s counterclaims, Tarpon Bay
    Partners LLC v. Zerez Holdings Corp. (Tarpon Bay II), 
    547 F. Supp. 3d 195
     (D. Conn. 2021).
    In the first summary judgment decision, dated September 24,
    18
    2019, the district court denied summary judgment for Tarpon Bay on
    the Affirmative Claims. First, there remained “a question of material
    fact with respect to whether the” Signing Fee Note “was supported
    by adequate consideration.” Tarpon Bay I, 
    2019 WL 4646061
    , at *7.
    Second, the Signing Fee Note was “unconscionable and, therefore,
    unenforceable.” 
    Id. at *8
    . The district court held that the Signing Fee
    Note was procedurally unconscionable because “[t]he undisputed
    facts of the case show that Tarpon Bay very clearly exploited its
    superior bargaining power over Zerez, which was on the verge of
    financial collapse, in order to control the terms of the agreement, and
    resultant partnership, and deprive Zerez of any meaningful choice in
    the agreement.” 
    Id. at *10
    . It also concluded that the Signing Fee Note
    was substantively unconscionable because the “terms . . . are
    extremely one-sided in Tarpon Bay’s favor” and it would be entitled
    19
    to $25 million 11 “for little to nothing in return.” Tarpon Bay I, 
    2019 WL 4646061
    , at *10. But despite holding that the Signing Fee Note was
    unenforceable, the district court denied Tarpon Bay’s motion for
    summary judgment without expressly indicating that the Affirmative
    Claims were dismissed as a matter of law or entering partial judgment
    for any party.        The district court also denied without prejudice
    Counterclaim Defendants’ summary judgment motion on Zerez’s
    counterclaims because Zerez had indicated that it would likely
    abandon those counterclaims if the Signing Fee Note were deemed
    unconscionable. 
    Id. at *11
    .
    Shortly after the decision, Tarpon Bay moved to certify the
    11The September 2019 decision initially stated that Tarpon Bay would be
    “entitled to $25 million for little to nothing in return. . . . It cannot be that Tarpon
    Bay receives [a] $25 million windfall with no promise in return or, at most, a
    promise to attempt to retire Zerez’s debt.” Tarpon Bay I, 
    2019 WL 4646061
    , at *10.
    But the July 2021 decision acknowledged that the $25 million sum represents the
    damages that Tarpon Bay sought, not the value of the stock requested under the
    Signing Fee Note. The latter was valued at $2.23 million at the time of conversion.
    While it is unclear how Tarpon Bay calculated the $25 million sum for damages,
    we agree with the district court’s July 2021 decision that the appropriate number
    to consider is $2.23 million, not $25 million. Tarpon Bay II, 547 F. Supp. 3d at 209
    n.6.
    20
    September 2019 order for interlocutory appeal to this court pursuant
    to 
    28 U.S.C. § 1292
    (b). 12 Joint App’x at 13. The district court denied
    the motion to certify in October 2019, concluding that its ruling did
    “not involve a controlling question of law” but rather “the application
    of undisputed facts in this case to the well-settled Connecticut law of
    unconscionability.” Tarpon Bay Partners LLC v. Zerez Holdings Corp.,
    No. 3:17CV00579(SRU), 
    2019 WL 10984250
    , at *2 (D. Conn. Oct. 29,
    2019). Zerez decided to pursue its counterclaims notwithstanding the
    September 2019 decision, and Counterclaim Defendants renewed
    their motion for summary judgment on Zerez’s counterclaims. Joint
    App’x at 1438. Zerez also moved for partial summary judgment on
    12   Section 1292(b) states in relevant part:
    When a district judge, in making in a civil action an order not
    otherwise appealable under this section, shall be of the opinion that
    such order involves a controlling question of law as to which there
    is substantial ground for difference of opinion and that an
    immediate appeal from the order may materially advance the
    ultimate termination of the litigation, he shall so state in writing in
    such order.
    
    28 U.S.C. § 1292
    (b).
    21
    two of its eleven counterclaims, both of which it pursues on appeal:
    Counterclaim Two, seeking declaratory judgment as to Zerez’s
    obligations under the Signing Fee Note, and Counterclaim Eleven,
    alleging a violation of CUTPA. 
    Id.
     at 1806–07.
    In the second summary judgment decision, dated July 7, 2021,
    the district court granted in part and denied in part Counterclaim
    Defendants’ and Zerez’s motions for summary judgment. Tarpon Bay
    II, 547 F. Supp. 3d at 227. Notably, the court granted summary
    judgment for Zerez on Counterclaim Two and concluded that
    “[b]ecause the Signing Fee Note is unconscionable and unenforceable,
    Zerez has no rights or obligations under the Signing Fee Note.” Id. at
    217. The court also granted summary judgment for Counterclaim
    Defendants on the CUTPA claim for two reasons: the deceptive
    conduct alleged was duplicative of the unconscionability claim, and
    Zerez had not established that it suffered an ascertainable loss under
    the statute. Id. at 223–24. As to Zerez’s other counterclaims, judgment
    22
    was either entered for Counterclaim Defendants, or the counterclaims
    were dismissed as moot. Id. at 210, 227. The district court entered
    judgment on the eleven counterclaims and closed the case, but it did
    not enter judgment on the Affirmative Claims. Judgment at 1–2,
    Tarpon     Bay    Partners    LLC     v.   Zerez     Holdings    Corp.,   No.
    3:17CV00579(SRU) (D. Conn. July 8, 2021).
    The relevant dispositions from the district court’s September
    2019 and July 2021 opinions are summarized in the following table:
    AFFIRMATIVE CLAIMS
    Decided in September 2019
    Claim Asserted by                       Disposition of Tarpon Bay’s
    No.                     Defendant
    Tarpon Bay                               Mot. for Summ. J.
    Delivery of
    1.                              Zerez                  Denied
    278,958,900 shares
    2.      Declaratory relief      Zerez                  Denied
    3.   Award of damages           Zerez                  Denied
    COUNTERCLAIMS ON APPEAL
    Decided in July 2021
    Disposition of          Disposition
    Counterclaim                   Countercl.              of Zerez’s
    No.                           Defendant
    Asserted by Zerez              Defs.’ Mot. for         Partial Mot.
    Summ. J.              for Summ. J.
    23
    Tarpon
    2.      Declaratory relief                 Denied           Granted
    Bay
    Violation of       Countercl.
    11.                                         Granted          Denied
    CUTPA              Defs.
    Tarpon Bay timely appealed from the Judgment, and Zerez
    timely cross-appealed.         Joint App’x at 1970, 2006.     The parties
    participated in the Second Circuit’s mediation program, but the case
    was ultimately reinstated on March 24, 2022.
    II.      Jurisdiction and Standard Of Review
    Before turning to the merits of the dispute, we first address an
    issue that affects our jurisdiction. We have jurisdiction over “appeals
    from all final decisions of the district courts of the United States.” 
    28 U.S.C. § 1291
    . “Finality is determined on the basis of pragmatic, not
    needlessly rigid pro forma, analysis. . . . What essentially is required is
    some clear and unequivocal manifestation by the trial court of its
    belief that the decision made, so far as it is concerned, is the end of the
    case.”     Fiataruolo v. United States, 
    8 F.3d 930
    , 937 (2d Cir. 1993).
    Although the parties do not challenge jurisdiction in this case, see
    24
    Appellants’ Br. at 1; Cross-Appellant’s Br. at 2, “we are obliged to
    raise the issue of our jurisdiction nostra sponte when it is
    questionable.” Massaro v. Palladino, 
    19 F.4th 197
    , 208 (2d Cir. 2021)
    (internal quotation marks and citation omitted).
    The district court denied summary judgment for Tarpon Bay in
    its September 2019 order “with respect to [Tarpon Bay’s] three claims
    against Zerez because the purported agreement is unconscionable as
    a matter of law,” Tarpon Bay I, 
    2019 WL 4646061
    , at *12, but did not
    enter judgment on those three claims—the Affirmative Claims—in
    favor of any party.   See Judgment at 1–2.      Denials of summary
    judgment are “by their terms interlocutory” and ordinarily not
    reviewable absent a final judgment disposing of the claims. Ortiz v.
    Jordan, 
    562 U.S. 180
    , 188 (2011) (internal quotation marks and citation
    omitted). A denial of summary judgment for one party on the claims
    it has raised, without an accompanying grant of summary judgment
    for the opposing party on the same claims, would ordinarily mean
    25
    that the status quo is preserved and the claims proceed to trial. But
    we have clear indication here that the district court meant otherwise.
    The subsequent July 2021 order—which entered summary judgment
    only on Zerez’s counterclaims, not Tarpon Bay’s Affirmative
    Claims—stated that “[a]s a result of [the court’s] rulings, no claims
    remain[ed] live in this action.” 13 Tarpon Bay II, 547 F. Supp. 3d at 211.
    We therefore interpret the district court’s September 2019 order
    denying summary judgment for Tarpon Bay to also include a grant of
    summary judgment for Zerez on the Affirmative Claims. Summary
    judgment is appropriate “if the movant shows that there is no genuine
    dispute as to any material fact and the movant is entitled to judgment
    13  Moreover, in the October 2019 decision denying Tarpon Bay’s motion for
    certification to the Second Circuit, the district court suggested that the
    unconscionability ruling was dispositive of all three of Plaintiff’s breach of contract
    claims. See Tarpon Bay, 
    2019 WL 10984250
    , at *2 & n.1 (noting also that the
    September 2019 “Ruling is not dispositive of the case as a whole” because “Zerez’s
    eleven counterclaims [were] still pending”). But as mentioned earlier, the district
    court nonetheless refrained from characterizing its September 2019 decision as a
    ruling on “a controlling question of law” but rather viewed it as an “application
    of undisputed facts . . . to the well-settled Connecticut law of unconscionability.”
    
    Id. at *2
    .
    26
    as a matter of law.” Fed. R. Civ. P. 56(a). “A material fact is one that
    would ‘affect the outcome of the suit under the governing law,’ and a
    dispute about a genuine issue of material fact occurs ‘if the evidence
    is such that a reasonable [factfinder] could return a verdict for the
    nonmoving party.’” Aetna Life Ins. Co. v. Big Y Foods, Inc., 
    52 F.4th 66
    ,
    72 (2d Cir. 2022) (alteration in original) (quoting Anderson v. Liberty
    Lobby, Inc., 
    477 U.S. 242
    , 248 (1986)). By ultimately holding that the
    Signing Fee Note was “unconscionable as a matter of law,” Tarpon Bay
    I, 
    2019 WL 4646061
    , at *12, the September 2019 decision necessarily
    concluded that any genuine issue of fact regarding consideration was
    not material. 14 See Anderson, 
    477 U.S. at 248
     (“Factual disputes that
    14 The district court reached two conclusions in the September 2019
    opinion: first, that “there is a question of material fact with respect to whether the
    Promissory Note was supported by adequate consideration,” and second, that
    “the Promissory Note was . . . unconscionable and, therefore, unenforceable.”
    Tarpon Bay I, 
    2019 WL 4646061
    , at *8 (emphasis added).
    But the second holding would have to render the “question of . . . fact with
    respect to whether the Promissory Note was supported by adequate
    consideration” not material. 
    Id.
              As discussed below, infra pp. 34–35,
    unconscionability is a defense to contract enforcement under Connecticut law. So
    even if Tarpon Bay had shown that there was no genuine issue of fact that
    27
    are irrelevant or unnecessary will not be counted.”). Put simply, the
    district court reasoned—without formally stating it—that summary
    judgment for Zerez on the Affirmative Claims was proper. Later, in
    July 2021, the district court entered judgment on Zerez’s
    counterclaims, which were the only live claims that remained in the
    case. See Judgment at 1–2. After that point, “there was nothing left
    for the district court to decide that would have affected the respective
    positions of the parties.” Massaro, 19 F.4th at 208–09. The July 2021
    Judgment was therefore “final” under 
    28 U.S.C. § 1291
    . And because
    the September 2019 summary judgment order merges into the July
    2021 final judgment on appeal, we have jurisdiction to review both
    decisions. See Gold v. N.Y. Life Ins. Co., 
    730 F.3d 137
    , 144 (2d Cir. 2013)
    (merging earlier summary judgment decisions into the judgment
    consideration supported the Signing Fee Note, the district court’s legal
    determination that the contract was unconscionable would have still meant that
    the contract is unenforceable. Facts relating to consideration should have,
    therefore, been deemed not material for summary judgment purposes. See
    Anderson, 
    477 U.S. at 248
     (“Only disputes over facts that might affect the outcome
    of the suit under the governing law will properly preclude the entry of summary
    judgment.”).
    28
    upon timely appeal).
    Tarpon Bay also asks us to review the district court’s denial of
    its motion for summary judgment on the Affirmative Claims. The
    denial of a motion for summary judgment is usually not immediately
    appealable. See 
    id.
     at 144 n.4; Spavone v. N.Y. State Dep’t of Corr. Servs.,
    
    719 F.3d 127
    , 133 (2d Cir. 2013) (applying the collateral order doctrine,
    which renders some summary judgment denials immediately
    appealable, in a qualified immunity case). But the more precise
    jurisdictional question here is not whether the denial is immediately
    appealable, but whether the denial becomes reviewable upon appeal
    from final judgment.      In cases where appeal is taken from final
    judgment, we have the discretion to review a denial of summary
    judgment that accompanies a grant of summary judgment on cross-
    motion. See Barhold v. Rodriguez, 
    863 F.2d 233
    , 237 (2d Cir. 1988) (“[A]s
    we have jurisdiction to decide [the appellants’] appeal from the
    granting of [the appellees’] motion for summary judgment, we
    29
    exercise our discretion to decide [the appellants’] claim of error in the
    denial of their summary judgment motion as well.”); see also Gary
    Friedrich Enters., LLC v. Marvel Characters, Inc., 
    716 F.3d 302
    , 320 (2d
    Cir. 2013) (“Because we have jurisdiction over the grant of summary
    judgment, we have the discretion to review the otherwise
    unappealable order denying [the appellants’] cross-motion for
    summary judgment.” (citing Barhold, 
    863 F.2d at 237
    )); see also Am.
    Motorists Ins. Co. v. United Furnace Co., 
    876 F.2d 293
    , 302 (2d Cir. 1989)
    (citing Barhold, 
    863 F.2d at 237
    ) (similar). 15
    Because we interpret the September 2019 order denying
    15 Gold does not compel a different result here. In that case, the court
    “decline[d] to review the district court’s decision” and explained that “[w]here a
    district court has denied summary judgment because resolution of such claim
    requires the adjudication of issues of fact that are inseparable from the merits, the
    denial of such motion is not immediately appealable notwithstanding the merger
    doctrine.” Gold, 
    730 F.3d at
    144 n.4. But the denial of summary judgment in Gold
    was not on cross-motion to the grant of summary judgment that the court
    reviewed; the motions underlying the grant and denial requested summary
    judgment on independent causes of action at different stages in the litigation
    before the district court. See 
    id.
     at 140–41.
    By contrast, Barhold’s line of cases establishes that we may review denials
    of summary judgment that accompany grants on cross-motion. And each of those
    cases reviewed denials of summary judgment for questions of fact or mixed
    30
    summary judgment for Tarpon Bay on the Affirmative Claims to also
    grant summary judgment for Zerez, the district court’s denial and
    corresponding sua sponte grant disposed of the Affirmative Claims
    on what effectively were cross-motions for summary judgment. Cf.
    Coach Leatherware Co. v. AnnTaylor, Inc., 
    933 F.2d 162
    , 167 (2d Cir. 1991)
    (“[I]t is most desirable that the court cut through mere outworn
    procedural niceties and make the same decision as would have been
    made had [the nonmoving party] made a cross-motion for summary
    judgment.” (quoting Local 33, Int’l Hod Carriers Bldg. & Common
    Laborers’ Union of Am. v. Mason Tenders Dist. Council of Greater N.Y.,
    
    291 F.2d 496
    , 505 (2d Cir. 1961))). Just as the merger doctrine extends
    our review from the final disposition in July 2021 to the earlier grant
    of summary judgment for Zerez in September 2019, see Gold, 
    730 F.3d at 144
    , it also extends our appellate jurisdiction to the corresponding
    denial of summary judgment for Tarpon Bay, see Marvel Characters,
    questions of law and fact. See Marvel, 
    716 F.3d at 320
    ; Am. Motorists, 
    876 F.2d at 303
    ; Barhold, 
    863 F.2d at 237
    .
    31
    
    716 F.3d at 320
    . For reasons of judicial economy, we exercise our
    discretion to review the denial here.
    We review the district court’s summary dispositions de novo.
    See 
    id.
       For summary judgment to be warranted, the evidence,
    construed in the light most favorable to the party against whom it was
    entered, must show that there is no genuine issue of material fact, and
    the moving party must be entitled to judgment as a matter of law. See
    Aetna Life Ins., 52 F.4th at 72; Fed. R. Civ. P. 56(a). The “mere existence
    of some alleged factual dispute” is insufficient to reverse a grant of
    summary judgment. Anderson, 
    477 U.S. at
    247–48.
    III.   Discussion
    The parties present three questions on appeal. First, Tarpon
    Bay challenges the district court’s ruling that the Signing Fee Note
    was unconscionable. Second, Tarpon Bay argues that the district
    court erred in determining that there remained a genuine issue of
    material fact as to whether consideration supported the Signing Fee
    Note. And third, Zerez challenges on cross-appeal the district court’s
    32
    grant of summary judgment for Tarpon Bay on Counterclaim Eleven,
    which alleged that Counterclaim Defendants violated CUTPA.
    For the reasons discussed below, we first vacate the district
    court’s ruling that the Signing Fee Note was unconscionable as a
    matter of law, on the record before it at summary judgment. We then
    conclude that the district court correctly determined that genuine
    issues of material fact remained as to whether consideration
    supported the Signing Fee Note. The district court’s dismissal of the
    Affirmative Claims is therefore also vacated, and the denial of
    summary judgment for Tarpon Bay is affirmed. 16 Finally, we affirm
    the district court’s grant of summary judgment on Zerez’s CUTPA
    counterclaim on the alternative ground that CUTPA does not apply
    16 The district court also dismissed as moot Counterclaims Five
    (Rescission), Six (Fraud), Seven (Mistake), Nine (Civil Conspiracy), and parts of
    Counterclaim Two (Declaratory Relief) because the relief sought by those
    counterclaims was duplicative of its September 2019 holding that the Signing Fee
    Note was unenforceable. Tarpon Bay II, 547 F. Supp. 3d at 216–18, 220. Zerez has
    not pursued those claims on appeal.
    33
    to the case at bar.
    A.     Unconscionability
    The Signing Fee Note makes clear that Connecticut law governs
    the dispute. Joint App’x at 1008. Under Connecticut law, the doctrine
    of unconscionability is a defense to contract enforcement that is
    intended “to prevent oppression and unfair surprise.” 17 Cheshire
    Mortg. Serv., Inc. v. Montes, 
    223 Conn. 80
    , 87–88 (1992) (internal
    quotation marks and citation omitted). “The classic definition of an
    unconscionable contract is one which no man in his senses, not under
    delusion, would make, on the one hand, and which no fair and honest
    man would accept, on the other.” Bender v. Bender, 
    292 Conn. 696
    ,
    731–32 (2009) (internal quotation marks and citation omitted). The
    question of whether a contract is unconscionable “is a matter of law
    to be decided by the court based on all the facts and circumstances of
    17In reviewing the district court’s unconscionability ruling, we assume
    arguendo that there are genuine issues of material fact regarding whether the
    Signing Fee Note was part of a validly formed contract between Tarpon Bay and
    Zerez. See infra section III.B.
    34
    the case.” Cheshire, 
    223 Conn. at 87
     (internal quotation marks and
    citation omitted).
    Like those of many other jurisdictions, Connecticut courts have
    parsed the unconscionability inquiry into procedural and substantive
    prongs. See Restatement (Second) of Conts. § 208 (Am. L. Inst. 1981)
    (collecting cases by jurisdiction).            A successful unconscionability
    defense “‘generally requires a showing that the contract was both
    procedurally and substantively unconscionable when made—i.e.,
    some showing of an absence of meaningful choice on the part of one
    of the parties together with contract terms which are unreasonably
    favorable to the other party.’” Bender, 
    292 Conn. at 732
     (quoting Hottle
    v. BDO Seidman, LLP, 
    268 Conn. 694
    , 719 (2004)). 18 Procedural
    18  The district court cited Bender but nonetheless stated that “only
    substantive unconscionability is required.” Tarpon Bay I, 
    2019 WL 4646061
    , at *9.
    When determining the applicable law as it would be applied by the state courts in
    diversity cases, federal courts must consult the forum state’s constitution, statutes,
    and highest court. See Erie R. Co. v. Tompkins, 
    304 U.S. 64
    , 78 (1938); Chufen Chen v.
    Dunkin’ Brands, Inc., 
    954 F.3d 492
    , 497 (2d Cir. 2020); Travelers Ins. Co. v. 633 Third
    Assocs., 
    14 F.3d 114
    , 119 (2d Cir. 1994). We conclude that the district court’s
    35
    holding ultimately does not follow the Connecticut Supreme Court’s most recent
    authority on unconscionability.
    Noting that the quotation in Bender derived from Hottle v. BDO Seidman, a
    Connecticut Supreme Court case interpreting New York law, see 
    268 Conn. at
    719–
    20 (citing Gillman v. Chase Manhattan Bank, N.A., 
    73 N.Y.2d 1
    , 10 (1988)), the district
    court relied instead on an earlier case applying Connecticut law. See Smith v.
    Mitsubishi Motors Credit of Am., Inc., 
    247 Conn. 342
    , 353 (1998) (“Even in the absence
    of procedural unconscionability, [the defendant] might avoid liability . . . if he
    could establish that the clause was substantively unconscionable.”); Tarpon Bay I,
    
    2019 WL 4646061
    , at *9. But notwithstanding its New York origins, the Bender rule
    is controlling here. Bender interpreted Connecticut contract law, see 
    292 Conn. at
    730–31 (collecting Connecticut cases on unilateral mistake), and applied the Hottle
    quotation as part of Connecticut contract law, see 
    id.
     at 732–34 & n.26 (following its
    recitation of the Hottle quotation with an evaluation of both procedural and
    substantive unconscionability). What was once a statement of New York law is
    now adopted into Connecticut law. The Bender Court’s general requirement that
    both unconscionability prongs be established is, therefore, “state law as
    announced by the highest court of the State,” and we are compelled to apply it.
    Comm’r v. Bosch’s Est., 
    387 U.S. 456
    , 465 (1967).
    Smith may still supply an exception to the general rule in Bender. The
    Bender court only “generally require[d]” both unconscionability prongs and, in its
    statement of the rule on unconscionability, approvingly quoted another portion of
    Smith; the court did not appear to view the two cases in tension. See 
    292 Conn. at
    731–32 (emphasis added). The Connecticut Supreme Court has never overruled
    or otherwise cast doubt on its unconscionability analysis in Smith. Moreover, the
    Hottle case—from which Bender derived its standard—held that under New York
    law, a contract may be rendered “unenforceable solely on the ground of
    substantive unconscionability.” Hottle, 
    268 Conn. at
    720–21 (citing Gillman, 
    73 N.Y.2d at 12
    ).
    But acknowledging that Smith may provide an exception to Bender’s
    general rule is not to say that only substantive unconscionability is required.
    Equating the two elides a question of degree. Proving oppressive terms under
    two-pronged unconscionability is already a difficult task, but prevailing on
    substantive unconscionability alone would require an even more onerous showing
    of oppression. Cf. Hottle, 
    268 Conn. at 721
     (“[P]rocedural and substantive
    unconscionability operate on a ‘sliding scale’; the more questionable the
    36
    unconscionability relates to the “process by which the allegedly
    offensive terms found their way into the agreement.” Cheshire, 
    223 Conn. at
    87 n.14 (internal quotation marks and citation omitted). It
    applies when there was “an absence of meaningful choice” by one of
    the parties. Bender, 
    292 Conn. at 732
     (internal quotation marks
    omitted). Substantive unconscionability, by contrast, relates to “the
    content of the contract,” Cheshire, 
    223 Conn. at
    87 n.14 (internal
    quotation marks and citation omitted), and applies when contract
    terms are “unreasonably favorable” to one party, Bender, 292 Conn. at
    meaningfulness of choice, the less imbalance in a contract’s terms should be
    tolerated and vice versa.” (quoting State v. Wolowitz, 
    468 N.Y.S.2d 131
    , 145 (App.
    Div. 1983))). To date, no Connecticut appellate court has determined how extreme
    the facts may be to justify application of the Smith exception. And recent cases
    have all cited the Bender, not Smith, rule on unconscionability. See Hirsch v.
    Woermer, 
    184 Conn. App. 583
    , 589 (2018); Emeritus Senior Living v. Lepore, 
    183 Conn. App. 23
    , 29 (2018); Bank of Am., N.A., v. Aubut, 
    167 Conn. App. 347
    , 379–380 (2016);
    R.F. Daddario & Sons, Inc. v. Shelansky, 
    123 Conn. App. 725
    , 741 (2010). But see
    Velasco v. Comm’r of Corr., 
    214 Conn. App. 831
    , 841–42 (questioning but ultimately
    declining to clarify the status of Smith after Bender), cert. denied, 
    345 Conn. 960
    (2022); Shoreline Commc’ns, Inc. v. Norwich Taxi, LLC, 
    70 Conn. App. 60
    , 70–71 (2002)
    (stating that the court “know[s] of no case, and the defendant has cited none, in
    which a party may invoke unconscionability without a showing of some kind of
    relevant misconduct by the party seeking enforcement of a contract,” but then
    evaluating whether substantive unconscionability existed). The Smith exception
    ultimately falls far short of swallowing the Bender rule.
    37
    732 (internal quotation marks omitted). In short, the doctrine of
    procedural unconscionability is “intended to prevent unfair
    surprise,” and the doctrine of substantive unconscionability is
    “intended to prevent oppression.” Smith, 
    247 Conn. at 349
    .
    Prevailing on unconscionability is generally difficult, and for
    good reason. It asks the court to step in and undo the allocation of
    risk in a contract. While courts have the power “to police explicitly
    against     the   contracts   or   clauses   which   they   find   to   be
    unconscionable,” the principle underpinning unconscionability “is
    one of the prevention of oppression and unfair surprise . . . and not of
    disturbance of allocation of risks because of superior bargaining
    power.” U.C.C. § 2-302 cmt. 1 (Am. L. Inst. & Unif. L. Comm’n 1977)
    (citation omitted). 19
    Unconscionability has its origins in Roman law doctrines of
    Connecticut has adopted verbatim section 2-302 of the Uniform
    19
    Commercial Code (“UCC”), which reads in relevant part:
    38
    “just price” and in English courts of equity; it serves as a flexible last
    resort when other contract law doctrines are unable to redress the
    injustice at issue. See Robert E. Scott & Jody S. Kraus, Contract Law
    and Theory 501, 507–08 (2013); U.C.C. § 2-302 cmt. 1. Procedural
    unconscionability fills in the gaps left by other doctrines intended to
    regulate the bargaining process, such as incapacity, fraud, and duress.
    Substantive unconscionability is similar to, but more pliable than, the
    invalidation of contract on public policy grounds. But an overly
    expansive      unconscionability        doctrine      would      undermine        the
    countervailing principles that “courts do not unmake bargains
    If the court as a matter of law finds the contract or any clause of the
    contract to have been unconscionable at the time it was made the
    court may refuse to enforce the contract, or it may enforce the
    remainder of the contract without the unconscionable clause, or it
    may so limit the application of any unconscionable clause as to
    avoid any unconscionable result.
    Conn. Gen. Stat. § 42a-2-302(1). Although article 2 of the UCC applies only to
    “transactions in goods” and does not strictly apply here, id. § 42a-2-102,
    Connecticut courts have looked to the UCC as “a useful guide in examining a claim
    of unconscionability.” Texaco, Inc. v. Golart, 
    206 Conn. 454
    , 461–62 (1988); see also,
    e.g., Cheshire, 
    223 Conn. at
    88–89; Hamm v. Taylor, 
    180 Conn. 491
    , 495 (1980).
    39
    unwisely made,” and that parties have the autonomy to bargain and
    allocate risks as they please. Osborne v. Locke Steel Chain Co., 
    153 Conn. 527
    , 533 (1966); see also Kent Literary Club of Wesleyan Univ. v. Wesleyan
    Univ., 
    338 Conn. 189
    , 241 (2021) (“It is axiomatic that courts do not
    rewrite contracts for the parties.” (internal quotation marks and
    citation omitted)). In short, “‘unconscionability’ cannot be equated
    with ‘harshness’ as an abstract matter.”            Arthur Allen Leff,
    Unconscionability and the Code—the Emperor’s New Clause, 
    115 U. Pa. L. Rev. 485
    , 540 (1967).
    Moreover, an unconscionability claim is typically reserved for
    vulnerable consumers seeking to prevent enforcement of exploitative
    terms by relatively more sophisticated businesses. See Emlee Equip.
    Leasing Corp. v. Waterbury Transmission, Inc., 
    31 Conn. App. 455
    , 465
    (1993) (“Although [certain] provisions might be unconscionable in an
    ordinary consumer lease, a different conclusion may follow where, as
    here, the contract is a commercial finance lease executed by two
    40
    corporate entities.”); Iamartino v. Avallone, 
    2 Conn. App. 119
    , 126
    (1984) (“The loan was a commercial, not a consumer, transaction.”);
    cf. Cheshire, 
    223 Conn. at
    124–25 (Berdon, J., dissenting in part and
    concurring in part) (stating that the majority reviewed the case
    “through the lens of commercially savvy parties” instead of “between
    a professional mortgage lender and unsophisticated credit consumers
    who had a total monthly income below the poverty level”). Indeed,
    “[c]ourts do not generally find contracts unconscionable where the
    parties are businesspersons.” Stamford Hosp. v. Schwartz, 
    190 Conn. App. 63
    , 76 (2019) (quoting Emlee, 31 Conn. App. at 464); see also 1
    James J. White, Robert S. Summers & Robert A. Hillman, Uniform
    Commercial Code § 5:3 (6th ed. 2020) (“The modal successful
    unconscionability claimant is a consumer of small means who has
    purchased a television or the like for a price that well exceeds the price
    available at stores where the middle class shop.”). Where commercial
    parties engage in arm’s-length negotiations and are sufficiently
    41
    sophisticated to understand the agreements they execute, raising the
    unconscionability defense asks the court to reconstruct economic
    outcomes. We decline to do so in this case.
    First, the Signing Fee Note is not procedurally unconscionable.
    Both Zerez and Tarpon Bay are sophisticated commercial parties:
    Zerez is publicly traded, and both parties routinely invest in other
    companies. Murga, Zerez’s then-CEO, was personally involved in the
    discussions with Aswani and had the opportunity to review the terms
    before signing. While Zerez alleges that Murga played no role in
    drafting the Signing Fee Note, there is no indication that Murga ever
    asked to edit any of the Signing Fee Note’s provisions. See Joint App’x
    at 917, 1297, 1303; see also Smith, 
    247 Conn. at
    351–52 (“We have never
    held that principles of unconscionability supersede, in toto, the duty
    of a contracting party to read the terms of an agreement or else be
    deemed to have notice of the terms.”). Moreover, Zerez had counsel
    on retainer at the time of the Signing Fee Note’s execution. In an
    42
    invoice for services rendered from October 2015 to February 2016—
    which overlapped with the execution of the Term Sheet and Signing
    Fee Note in January 2016—attorney Mark H. Cheung billed $30,000
    to Zerez for legal work on “promissory notes” and “review of
    contractual matters.” Joint App’x at 1259. The record at this stage
    does not reveal whether Cheung reviewed or otherwise had a role in
    negotiating the Term Sheet and Signing Fee Note in January 2016.20
    But even if Cheung did not review the contracts for Zerez, Zerez
    cannot now claim hardship where it was able to solicit legal advice on
    the Signing Fee Note if it felt coerced or did not understand the terms’
    implications.     See Cheshire, 
    223 Conn. at
    90–91 (finding that an
    attorney’s explanation to the defendants of a loan’s terms supported
    the trial court’s finding that the loan was not procedurally
    20  Cheung must have been aware of the section 3(a)(10) transaction by April
    2016 because his law office was also a creditor of Zerez whom Tarpon Bay had
    engaged with a Claim Purchase Agreement; moreover, Cheung was the person
    who, in September 2016, emailed Aswani that he, along with two other creditors,
    were cancelling their Claim Purchase Agreements once the deal had broken down.
    See id. at 1178, 1245–46, 1248.
    43
    unconscionable). Zerez’s failure to consult with readily available
    counsel, in these circumstances, precludes a finding of procedural
    unconscionability.
    Zerez also argues that the Signing Fee Note was procedurally
    unconscionable because its business desperately needed to retire its
    debt, and the company was “susceptible to coercion” because “it was
    presented with only one choice to address its debt.”            Cross-
    Appellant’s Br. at 29. Zerez maintains that because Aswani told
    Murga that “signing of the Note was a prerequisite to entering in[to]
    a definitive agreement,” Murga understood that he “had no
    meaningful choice in negotiating its terms given Zerez’s financial
    condition.” Id. at 30 (citations to record omitted). But Zerez could
    have walked away or engaged other parties if it did not like Aswani’s
    terms. Zerez received cold calls from multiple entities yet nonetheless
    chose to proceed with Tarpon Bay. Joint App’x at 871. Murga himself
    suggested that Zerez had options. He stated in a sworn declaration
    44
    that “Zerez would not have agreed to move forward with Southridge
    or Tarpon” if it knew that Hicks, facing unrelated allegations of
    securities fraud, was involved in the transaction. Id. at 1151–52. And
    after the transaction with Tarpon Bay had failed, Zerez was able to
    merge in a newly acquired subsidiary, which involved the issuance of
    two billion new shares and a change in company management. See
    id. at 967. Zerez may not have had many options, but it had more
    than one.     See Marcus Dairy, Inc. v. Rollin Dairy Corp., No.
    3:05CV00589(PCD), 
    2008 WL 4425954
    , at *11 (D. Conn. Sept. 24, 2008)
    (finding no unconscionability where defendant received pricing
    information from several other suppliers before choosing plaintiff).
    Nor does Zerez argue that its financial distress—the $500,000 of debt
    on its books and resulting need for new capital—was somehow
    caused by Tarpon Bay’s actions. See Krishnamurti v. Tortorici, No. FST-
    CV19-6042031-S, 
    2021 WL 2403325
    , at *7 (Conn. Super. Ct. May 21,
    2021) (“Any financial pressure that the defendant was under was not
    45
    caused in any way by the plaintiff.”). Even when construed in favor
    of Zerez, the circumstances surrounding execution of the Signing Fee
    Note do not rise to the level of unfair surprise, lack of knowledge of
    terms, lack of legal representation, and absence of meaningful choice
    that characterizes procedural unconscionability.
    Nor are the terms of the Signing Fee Note substantively
    unconscionable. Zerez argues that the Signing Fee Note is oppressive,
    even if redemption were limited to $25,000 in cash, because it was
    redeemed “for nothing” in return. Cross-Appellant’s Br. at 24. That
    argument fails as a matter of law. “The general rule is that, in the
    absence of fraud or other unconscionable circumstances, a contract
    will not be rendered unenforceable at the behest of one of the
    contracting   parties   merely     because   of   an     inadequacy   of
    consideration.” Rockstone Cap., LLC v. Caldwell, 
    206 Conn. App. 801
    ,
    815 (2021) (quoting, ultimately, Osborne, 
    153 Conn. at 533
    ) (reversing
    trial   court’s   holding   that    agreement      was     substantively
    46
    unconscionable     because     defendant      received    “no    direct
    consideration”), cert. denied, 
    339 Conn. 914
     (2021) . To hold otherwise
    misappropriates the unconscionability doctrine, meant for vulnerable
    contracting parties, for what is substantively a challenge to the
    adequacy of consideration.
    Zerez further contends that the Signing Fee Note is “even
    more” unconscionable “under the Note’s conversion provision” that
    resulted in the claim of 278,958,900 shares, worth $2.23 million. Cross-
    Appellant’s Br. at 24. In other words, Zerez challenges the method of
    payment of the Signing Fee—the conversion provision—rather than
    the fact that Zerez had to render payment at all ($25,000 or 278,958,900
    shares). This argument, too, fails.
    The Signing Fee Note allowed for two payment methods: (1)
    payment of a fixed $25,000 fee, in addition to accrued interest and
    other fees, or (2) payment of the same value in stock using a
    predetermined cash-to-stock conversion ratio, which was a “50%
    47
    discount from the lowest closing bid price in the 30 trading days
    prior” to the conversion notice. Joint App’x at 1006. Zerez, short on
    cash, might have benefitted from paying out a Signing Fee in stock.
    But penny stocks “are considered to be particularly high risk and not
    suitable to all investors,” SEC v. Bronson, 
    14 F. Supp. 3d 402
    , 404 n.1
    (S.D.N.Y. 2014); see also supra note 2, so in choosing an alternative
    payment method, Zerez agreed to a risky bet. Specifically, Zerez
    wagered that its stock price would remain low enough that Tarpon
    Bay would prefer stock to cash, yet stable enough that Zerez could
    issue the shares quickly before prices appreciated.       By contrast,
    Tarpon Bay wagered that the stock price would also remain low
    enough to prefer stock to cash, but sufficiently volatile that Tarpon
    Bay could opportunistically convert shares after a drastic price dip.
    The parties could have agreed to a straightforward payment of cash
    but instead executed—assuming consideration arguendo—the
    Signing Fee Note, which introduced market risk in determining the
    48
    payment method.       And a bet on the public markets between
    commercial parties, without more, does not constitute a “contract
    term[] which [is] unreasonably favorable” to the profiting party.
    Bender, 
    292 Conn. at 732
     (quoting Hottle, 
    268 Conn. at 719
    ).
    Zerez’s reliance on the conversion amount of $2.23 million to
    establish substantive unconscionability as a matter of law is also
    misplaced. The district court calculated the $2.23 million sum by
    multiplying the 278,958,900 shares that Tarpon Bay requested by
    $0.008, Zerez’s stock price on November 28, 2016, one day before the
    Notice of Conversion. See Tarpon Bay II, 547 F. Supp. 3d at 208; supra
    note 11.   But unconscionability is evaluated at the time of the
    contract’s formation, not at any time thereafter when the oppression
    allegedly took place. See Cheshire, 
    223 Conn. at 89
    . At the time of the
    contract’s formation, the Signing Fee Note obligated Zerez “to reserve
    at least Five hundred million (500,000,000) shares of its Common
    Stock for issuance to [Tarpon Bay] in connection with conversion of
    49
    this Note.” Joint App’x at 1011. The quantity of 278,958,900 shares—
    constituting 55.6 percent of the total amount of reserved shares—
    could not have been oppressive at the time of execution because Zerez
    agreed to a provision that expressly contemplated a conversion of up
    to 500,000,000 shares. And on at least ten occasions from December
    2014 to January 2016, Zerez had issued common stock pursuant to
    convertible promissory notes and compensation packages at
    conversion prices ranging from $0.0001—the same as Tarpon Bay’s
    requested conversion price—to $0.003. 21 See Appellants’ Br. at 22–23;
    Joint App’x at 959. Where the allegedly problematic conversion was
    contemplated by another provision in the Signing Fee Note and
    executed at a price consistent with prior share issuances, we cannot
    conclude that the Signing Fee Note payment method was oppressive
    21 The record is silent as to how these conversion prices were determined,
    and it is likewise unclear whether Zerez has in the past agreed to a conversion
    formula comparable to the formula in this case.
    50
    to Zerez.
    This case does not involve vulnerable consumers seeking relief
    from unfairly surprising and oppressive terms. Instead, we are asked
    to undo an investment deal that unevenly distributed risk among
    sophisticated parties.      For a commercial party like Zerez,
    unconscionability demands much more. Yes, the Signing Fee Note
    may have been executed under confusing circumstances, and yes, it
    may have featured terms benefitting one side more than the other.
    But that does not compel us to conclude on the record as currently
    developed that the Signing Fee Note—if it was a valid contract—was
    either unfairly surprising or oppressive. We vacate the district court’s
    September 2019 order dismissing Tarpon Bay’s claims on the basis
    that the Signing Fee Note is unenforceable. For the same reasons, we
    also vacate the district court’s grant of summary judgment on
    51
    Counterclaim Two. 22
    B.     Consideration
    In the same September 2019 order, the district court denied
    Tarpon Bay’s motion for summary judgment on the Affirmative
    Claims because “there is a question of material fact with respect to
    whether the [Signing Fee Note] was supported by adequate
    consideration.” Tarpon Bay I, 
    2019 WL 4646061
    , at *7. We affirm that
    ruling. The factual issues regarding consideration may reasonably be
    resolved in favor of either party, and consideration is material to
    whether Tarpon Bay may prevail on its Affirmative Claims. The
    Affirmative Claims are accordingly remanded for trial.
    “Under the law of contract, a promise is generally not
    22 Counterclaim Two sought a declaration of Zerez’s “rights and duties, if
    any, under the [Signing Fee] Note and any implied in fact contract and [a]
    declaration as to Tarpon’s obligations to provide any performance.” Joint App’x
    at 883. In July 2021, the district court granted summary judgment on Counterclaim
    Two because it had held in September 2019 that the Signing Fee Note was
    unconscionable and unenforceable. Tarpon Bay II, 547 F. Supp. 3d at 217. Because
    we here vacate the underlying unconscionability holding, we also vacate the grant
    of summary judgment on Counterclaim Two.
    52
    enforceable unless it is supported by consideration.”         Stewart v.
    Cendant Mobility Servs. Corp., 
    267 Conn. 96
    , 104 (2003) (internal
    quotation marks and citation omitted). Consideration “consists of a
    benefit to the party promising, or a loss or detriment to the party to
    whom the promise is made.” Viera v. Cohen, 
    283 Conn. 412
    , 440–41
    (2007) (internal quotation marks and citation omitted). A return
    promise for performance is sufficient consideration, so long as the
    party making the return promise does not have a preexisting duty to
    honor that return promise. See, e.g., Bilbao v. Goodwin, 
    217 A.3d 977
    ,
    988 (Conn. 2019); Christophersen v. Blount, 
    216 Conn. 509
    , 511 n.3
    (1990); see also Conn. Gen. Stat. § 42a-3-303(a) (“An instrument is
    issued or transferred for value if . . . [t]he instrument is issued or
    transferred for a promise of performance, to the extent the promise
    has been performed . . . .”).      It is longstanding precedent in
    Connecticut that “[i]n the case of . . . promissory notes, the expression
    for value received[] raises a presumption of . . . legal consideration.”
    53
    Alcantara v. Pimentel, No. UWY-CV13-6020129-S, 
    2017 WL 4621386
    , at
    *2 (Conn. Super. Ct. Aug. 21, 2017) (quoting Raymond v. Sellick, 
    10 Conn. 480
    , 484 (1835)). But a formal recitation of consideration, such
    as “for value received,” “is simply prima facie evidence, shifting the
    burden of proof to the party disputing the consideration.”           TIE
    Commc’ns, Inc. v. Kopp, 
    218 Conn. 281
    , 292 (1991) (citing Raymond, 
    10 Conn. at 483
    ).
    The Signing Fee Note reads in relevant part:
    FOR VALUE RECEIVED, the Company promises to pay
    Tarpon Bay Partners, LLC . . . the principal sum of
    Twenty Five Thousand Dollars and No Cents
    ($25,000.00) . . . or such lesser principal amount
    following the conversion or conversions of this Note in
    accordance        with  Paragraph   2 . . . payable on
    demand . . . .
    Joint App’x at 1005. Because this language “raises a presumption
    of . . . legal consideration,” Alcantara, 
    2017 WL 4621386
    , at *2 (quoting
    Raymond, 
    10 Conn. at 484
    ), the burden shifts to Zerez to establish a
    genuine issue of material fact which, if taken as true, would rebut the
    presumption. See Taft Realty Corp. v. Yorkhaven Enters., Inc., 
    146 Conn. 54
    338, 342–43 (1959); cf. Fieldpoint Priv. Sec. v. Fed. Ins. Co., No. FST-
    CV21-6049713-S, 
    2021 WL 5919792
    , at *5 (Conn. Super. Ct. Nov. 29,
    2021) (“In connection with a hypothetical summary judgment motion,
    the court presumably would have before it a factual record, such that
    if the defendant were to present evidence affirmatively establishing
    (on a prima facie basis) that no consideration had been paid to the
    plaintiff by the Bermuda claimants, the burden would shift to the
    plaintiff to establish a material issue of fact as to payment of fees (or
    establish the non-materiality of the issue of payment).”). Tarpon Bay
    contends on appeal that Zerez failed to rebut the “for value received”
    presumption, and accordingly argues that summary judgment on the
    Affirmative Claims should enter in its favor. See Appellants’ Br. at
    39–40, 45; Appellants’ Reply at 14–17.
    We disagree. Zerez raises genuine issues of material fact that
    may, if resolved in its favor at trial, rebut the presumption of
    consideration.   We discern from the parties’ summary judgment
    55
    arguments that there are three possible ways a contract could have
    been formed:
    1. The Term Sheet is an unenforceable agreement to agree.
    But the Signing Fee Note was executed by Zerez in
    exchange for a return promise by Tarpon Bay—made at
    some point after the Term Sheet was signed but before
    the Signing Fee Note was executed—to begin the section
    3(a)(10) transaction pursuant to the Term Sheet’s
    contemplated deal structure.
    2. The Term Sheet is an unenforceable agreement to agree.
    But the Signing Fee Note was an offer by Zerez to induce
    Tarpon Bay to proceed with the section 3(a)(10)
    transaction.    Tarpon Bay accepted that offer by
    commencing performance when it contacted creditors,
    executed Claim Purchase Agreements, and filed suit in
    Florida state court.
    3. The Term Sheet itself is a binding agreement. It includes
    a return promise by Tarpon Bay to begin the debt-for-
    equity transaction pursuant to the Term Sheet’s
    contemplated deal structure. The Signing Fee Note is
    effectively an addendum that specifies the Signing Fee
    provision of the Term Sheet in greater detail.
    We analyze the three possibilities in turn and conclude that Zerez
    meets its burden of production on rebutting each.
    The first option is precluded because Zerez submitted
    56
    deposition evidence that raised a genuine issue of material fact as to
    whether Tarpon Bay ever made a valid return promise to begin the
    section 3(a)(10) transaction. Hicks stated in his deposition testimony:
    Q. Did Tarpon Bay have any obligation to purchase the
    liabilities of Zerez at the time the note was executed?
    A. That certainly was the plan, and that’s what
    happened.
    Q. Do you have an understanding of whether that
    obligation existed at the time the promissory note was
    executed?
    A. I believe—I’m not a lawyer, but I believe that it was a
    valid note regardless of whether or not Tarpon Bay
    ultimately performed work.
    Joint App’x at 1203. If Tarpon Bay was entitled to the Signing Fee
    Note “regardless of whether or not Tarpon Bay ultimately performed
    work,” then there was no return promise to perform made by Tarpon
    Bay. 
    Id.
     The Signing Fee Note would then be an unenforceable
    executory promise. To be clear, there is record evidence suggesting
    that Tarpon Bay made a return promise. Aswani stated to Murga
    during the Signing Fee Note negotiations that Murga would need to
    57
    sign the Signing Fee Note in order to proceed because it was a
    prerequisite to entering into a definitive agreement. 
    Id. at 1152
    .
    Tarpon Bay also signed the Term Sheet one day after Zerez executed
    the Signing Fee Note, which could reflect the existence of a return
    promise.   And Tarpon Bay’s subsequent performance—when it
    contacted creditors, executed eight Creditor Purchase Agreements,
    and initiated a lawsuit in Florida state court—may also be evidence
    of a return promise. But because the factual issue of whether there
    was a return promise may reasonably be resolved in favor of either
    party, summary judgment under option one is unwarranted.
    The second option is precluded because the record does not
    clearly establish that the Signing Fee Note (separate and apart from
    the Term Sheet) was an offer that Tarpon Bay accepted by beginning
    performance. In its July 2021 decision, the district court evaluated
    Zerez’s counterclaim for “breach of implied contract” and reasoned:
    Some implied contract likely existed between the parties.
    Without executing the definitive documentation that the
    58
    Term Sheet called for, Tarpon Bay entered into Claim
    Purchase Agreements to acquire over $500,000 of Zerez’s
    outstanding debt and filed the Florida Case. It is difficult
    to believe that Tarpon Bay would have undertaken those
    actions if it thought that Zerez had made no return
    promises.
    Tarpon Bay II, 547 F. Supp. 3d at 212. Under this theory of implied
    contract, the Term Sheet was a nonbinding agreement to agree, and
    the Signing Fee Note was an offer by Zerez.          Tarpon Bay then
    accepted Zerez’s offer by return promise: not by verbally
    communicating a return promise, but by performance—namely
    contacting creditors, executing Claim Purchase Agreements, and
    filing the Florida lawsuit. See Restatement (Second) of Conts. § 50
    cmt. b (“[T]he beginning of performance or a tender of part
    performance    operates    as   a    promise    to   render   complete
    performance.”). Zerez was aware of Tarpon Bay’s actions—two of its
    corporate officers were creditors whom Tarpon Bay had engaged—
    yet never objected or attempted to revoke the Signing Fee Note.
    Under this implied contract theory, Zerez’s promise to pay the
    59
    Signing Fee was exchanged for Tarpon Bay’s return promise to
    initiate the section 3(a)(10) proceeding.
    But genuine issues of material fact remain as to whether there
    was valid offer and acceptance under this theory. An offer is a
    “manifestation of willingness to enter into a bargain, so made as to
    justify another person in understanding that his assent to that bargain
    is invited and will conclude it.” U.S. Bank Nat’l Ass’n v. Eichten, 
    184 Conn. App. 727
    , 773 (2018) (quoting Restatement (Second) of Conts. §
    24); see also Restatement (Second) of Conts. § 2 cmt. b (“A promisor
    manifests an intention if he believes or has reason to believe that the
    promisee will infer that intention from his words or conduct.”
    (emphasis added)). A factfinder may well conclude that, independent
    of Zerez’s subjective intent, Tarpon Bay was justified in
    understanding the Signing Fee Note to be an invitation to initiate the
    transaction.   Its execution, after all, shortly followed Aswani’s
    statement to Murga that the Signing Fee Note was meant to
    60
    compensate Tarpon Bay for transaction services and was a
    prerequisite to entering into a definitive agreement, and Murga did
    not say anything to the contrary. See Joint App’x at 1152. But as
    mentioned above, Hicks stated in deposition testimony that he
    believed Tarpon Bay was entitled to the Signing Fee Note “regardless
    of whether or not Tarpon Bay ultimately performed work.” Id. at
    1203. That evidence supports the contrary conclusion that Tarpon
    Bay did not understand the Signing Fee Note as an offer that, once
    accepted, would compel performance.         There is ultimately little
    evidence of “[t]he parties’ intentions manifested by their acts and
    words,” which “are essential to the court’s determination of whether
    a contract was entered into and what its terms were.” Auto Glass Exp.,
    Inc. v. Hanover Ins. Co., 
    293 Conn. 218
    , 225 (2009) (internal quotation
    marks and citation omitted). Because the questions of offer and
    acceptance are at the heart of this case and will benefit from a full
    61
    record at trial, the second option is foreclosed at summary judgment.
    Finally, the third option is precluded because the record does
    not clearly establish that the Term Sheet was a binding agreement.
    Indeed, the Term Sheet contains a caveat:
    The terms set forth above do not constitute a contractual
    commitment of the Company or the Purchaser, but
    merely represent proposed terms for possible liabilities
    satisfaction. Until definitive documentation is executed by
    all parties, there shall not exist any binding
    obligation . . . .
    Id. at 984 (emphasis added). The parties dispute the meaning and
    importance of “definitive documentation.” Zerez argues that because
    there was no “definitive documentation,” the Term Sheet does not
    represent a “binding obligation.” See Cross-Appellant’s Br. at 34.
    Hicks    testified   that   this paragraph was “leftover        from   a
    different . . . strategy” and unintentionally integrated into this
    transaction.    Joint App’x at 1206.     Yet he also testified that the
    “definitive agreement is the complaint” filed in state court, and that
    “the claims purchase agreements are really the first thing as far as
    62
    documentation is concerned.” Id. at 1204. Because the meaning and
    satisfaction of the “definitive documentation” requirement raise
    genuine issues of material fact as to whether the Term Sheet was
    binding, option three does not support summary judgment for
    Tarpon Bay. 23
    The record in this case presents several genuine issues of
    material fact as to whether there was consideration supporting the
    Signing Fee Note. Because these factual issues “may reasonably be
    resolved in favor of either party,” Anderson, 
    477 U.S. at 250
    , the district
    court correctly held that Zerez established a genuine dispute of
    material fact as to whether the Signing Fee Note was supported by
    consideration.     We affirm the district court’s denial of summary
    judgment and remand the issue of contract formation for further
    23 Tarpon Bay does not appear to argue that the Signing Fee Note was itself
    the “definitive documentation” that would render the Term Sheet binding. Hick’s
    deposition testimony, as well as Aswani’s statement to Murga that the Signing Fee
    Note was a prerequisite to entering into a definitive agreement, both suggest that
    “definitive documentation” referred to a document after the Signing Fee Note. Id.
    at 1152.
    63
    proceedings.
    C.     CUTPA
    Zerez also argues that the district court erred in granting
    summary judgment on Counterclaim Eleven, which alleged that
    Counterclaim Defendants violated CUTPA. See 
    Conn. Gen. Stat. §§ 42
    -110a to -110q.       A party seeking to “prevail on a CUTPA
    claim . . . must prove that (1) the defendant engaged in unfair or
    deceptive acts or practices in the conduct of any trade or commerce;
    and (2) each class member claiming entitlement to relief under
    CUTPA has suffered an ascertainable loss of money or property as a
    result of the defendant’s acts or practices.” Artie’s Auto Body, Inc. v.
    Hartford Fire Ins. Co., 
    287 Conn. 208
    , 217 (2008) (internal quotation
    marks and citations omitted); see also 
    Conn. Gen. Stat. § 42
    -110b(a), -
    110g(a). 24 The district court concluded that “Zerez simply assert[ed]
    24Under the CUTPA provisions relevant here, “[n]o person shall engage in
    unfair methods of competition and unfair or deceptive acts or practices in the
    conduct of any trade or commerce.” 
    Conn. Gen. Stat. § 42
    -110b(a). “Any person
    who suffers any ascertainable loss of money or property, real or personal, as a
    64
    a breach of contract claim in the guise of a CUTPA claim” and did not
    demonstrate an “ascertainable loss” cognizable under the statute.
    Tarpon Bay II, 547 F. Supp. 3d at 223. Because Zerez failed to establish
    a CUTPA claim, the district court determined that it “need not decide
    whether . . . CUTPA applies to the Signing Fee Note.” Id. Summary
    judgment entered for Counterclaim Defendants on that count
    accordingly. Judgment at 2.
    We affirm the district court’s grant of summary judgment on
    the alternative grounds that CUTPA does not apply to the case at
    bar. 25 “CUTPA does not apply to deceptive practices in the purchase
    result of the use or employment of a method, act or practice prohibited by section
    42-110b, may bring an action . . . to recover actual damages.” 
    Conn. Gen. Stat. § 42
    -
    110g(a).
    25 While the parties raised the issue of CUTPA’s applicability before the
    district court, see Joint App’x at 1867–68, they did not do so in their briefing before
    this court. An argument not raised on appeal is generally deemed abandoned. See
    United States v. Joyner, 
    313 F.3d 40
    , 44 (2d Cir. 2002). But rules concerning waiver
    are “prudential, not jurisdictional,” and we have exercised our discretion to review
    waived or abandoned arguments “where . . . the argument presents a question of
    law and there is no need for additional fact-finding.” Sniado v. Bank Aus. AG, 
    378 F.3d 210
    , 213 (2d Cir. 2004); see also United States v. Babwah, 
    972 F.2d 30
    , 35 (2d Cir.
    1992) (noting that a court of appeals has discretion to consider argument not raised
    on appeal “if manifest injustice otherwise would result”).
    65
    and sale of securities.” Russell v. Dean Witter Reynolds, Inc., 
    200 Conn. 172
    , 180 (1986).     Despite the broad sweep of CUTPA’s text
    encompassing “deceptive acts . . . in the conduct of any trade or
    commerce,” 
    Conn. Gen. Stat. § 42
    -110b(a) (emphasis added), “Federal
    Trade Commission (FTC) rulings and cases under the Federal Trade
    Commission Act . . . serve as a lodestar for interpret[ing]” CUTPA,
    Russell, 
    200 Conn. at 179
    . Because “[t]he FTC has never undertaken
    to adjudicate deceptive conduct in . . . transactions fall[ing] under the
    comprehensive regulatory umbrella of the Securities and Exchange
    Commission,” transactions governed by the federal securities laws
    likewise fall outside CUTPA’s ambit. 
    Id. at 180
    . That said, the
    securities carveout is not so broad that the mere involvement of stock
    in an allegedly deceptive act is sufficient to preclude CUTPA’s
    application.   See, e.g., Halo Tech Holdings, Inc. v. Cooper, No.
    3:07CV00489(AHN), 
    2008 WL 877156
    , at *19 (D. Conn. Mar. 26, 2008)
    (“[U]se of a stock sale simply as the means for effecting the transfer of
    66
    a corporation should not remove it from the purview of CUTPA,
    when CUTPA would clearly apply if a sale of assets occurred
    instead.” (internal quotation marks omitted) (quoting TIE/Commc’ns,
    Inc. v. Kopp, No. 64983, 
    1993 WL 515680
    , at *8 (Conn. Super. Ct. Nov.
    29, 1993)).
    CUTPA does not apply to the alleged deception in this case.
    Zerez alleges that “Counterclaim Defendants’ . . . acts violate the
    Connecticut Unfair Trade Practices Act . . . , in that their conduct was
    unfair, immoral, oppressive, unethical, unscrupulous and/or
    deceptive and has caused substantial injury to Zerez.” Joint App’x at
    890. But any deceptive conduct would have been in furtherance of
    the parties’ transaction, which intended a sale of debt for equity
    pursuant to section 3(a)(10) of the Securities Act.       Because the
    antifraud provisions of the federal securities laws would regulate
    allegedly deceptive conduct in section 3(a)(10) transactions, the
    dispute at bar falls outside of CUTPA’s scope. See Russell, 
    200 Conn. 67
    at 179–80.
    Upon supervision and approval by a judicial or administrative
    body, section 3(a)(10) of the Securities Act of 1933 may exempt an
    issuer from registering securities issued in exchange for outstanding
    securities or other qualifying value. See 15 U.S.C. § 77c(a)(10). The
    provision specifically exempts from registration:
    [A]ny security which is issued in exchange for one or
    more bona fide outstanding securities, claims or
    property interests, or partly in such exchange and partly
    for cash, where the terms and conditions of such issuance
    and exchange are approved, after a hearing upon the
    fairness of such terms and conditions at which all
    persons to whom it is proposed to issue securities in such
    exchange shall have the right to appear, by any court, or
    by any official or agency of the United States, or by any
    State or Territorial banking or insurance commission or
    other governmental authority expressly authorized by
    law to grant such approval . . . .
    Id.   Section 3(a)(10) transactions arise most frequently in three
    contexts: litigation settlement involving an exchange of shares,
    bankruptcy proceedings not subject to Chapter 11 of the Bankruptcy
    Code, or, as here, the reorganization or capital restructuring of solvent
    68
    businesses. See 7 J. William Hicks, Exempted Transactions Under the
    Securities Act of 1933 § 3:1 (2023).
    Despite their exemption from registration, see 15 U.S.C.
    § 77c(a), section 3(a)(10) transactions are still subject to the antifraud
    provisions of the Securities Act, see id. § 77q(c). Section 17(a) makes it
    illegal for “any person in the offer or sale of any securities . . . to
    employ any device, scheme, or artifice to defraud,” or “to engage in
    any transaction, practice, or course of business which operates or
    would operate as a fraud or deceit upon the purchaser.” 15 U.S.C.
    § 77q(a)(1), (3). Although there is a paucity of case law on point, it
    appears undisputed that allegedly fraudulent or deceptive conduct in
    the course of executing section 3(a)(10) transactions may indeed
    violate section 17(a) upon meeting all the requisite elements. See, e.g.,
    In re Am. Trailer Rentals Co., 
    325 F.2d 47
    , 52 & n.11 (10th Cir. 1963),
    rev’d on different grounds sub nom. SEC v. Am. Trailer Rentals Co., 
    379 U.S. 594
     (1965); SEC v. Johnson, No. 2:20CV08985(FWS), 
    2023 WL 69
    2628680, at *6–8 (C.D. Cal. Mar. 2, 2023); SEC v. Currency Trading Int’l,
    No. 02CV05143(PA), 
    2004 WL 2753128
    , at *6, 10 (C.D. Cal. Feb. 2,
    2004); SEC v. Granco Prods., 
    236 F. Supp. 968
    , 970 (S.D.N.Y. 1964); see
    also Staff Legal Bulletin No. 3A (CF), U.S. SEC (June 18, 2008),
    https://www.sec.gov/corpfin/staff-legal-bulletin-3a (stating the SEC’s
    view that “the anti-fraud requirements of the federal securities laws
    would govern disclosure” to parties to whom securities would be
    issued after a section 3(a)(10) transaction).
    Any attempt to separate the Signing Fee Note from the
    underlying scheme to effectuate a section 3(a)(10) transaction is
    ultimately unconvincing.      While one may confine the allegedly
    deceptive conduct to the Signing Fee Note rather than the transaction
    writ large, all parties agreed that the Signing Fee Note was executed
    pursuant to the Signing Fee provision in the Term Sheet. See Joint
    App’x at 1445 (“[I]n satisfaction of its obligation to pay Tarpon the
    Signing Fee, Zerez executed . . . the Signing Fee Note.”); 
    id.
     at 1298
    70
    (“Admitted and Zerez respectfully refers the Court to the referenced
    document for its complete terms.”). The Term Sheet, in turn, makes
    clear that the parties contemplated a debt-for-equity transaction
    under section 3(a)(10) that would be exempt from registration. See 
    id. at 981
    . Moreover, even if the motives behind the Signing Fee Note
    were limited to the Term Sheet’s stated purpose of covering Tarpon
    Bay’s “legal fees due upon the execution of the term sheet,” 
    id. at 983
    ,
    the Signing Fee Note’s option to convert the Signing Fee into Zerez
    stock renders it part of the larger securities transaction. See 15 U.S.C.
    § 77b(a)(3) (“Any security given or delivered with, or as a bonus on
    account of, any purchase of securities or any other thing, shall be
    conclusively presumed to constitute a part of the subject of such
    purchase and to have been offered and sold for value.”).
    CUTPA may not exceed its broad yet well-defined limits where
    the transactions “for the purchase and sale of securities” are such that
    the federal securities laws would apply. Russell, 
    200 Conn. at 180
    .
    71
    Because section 17(a) of the Securities Act would apply to allegedly
    deceptive behavior in a section 3(a)(10) transaction, CUTPA does not
    apply to Counterclaim Defendants’ alleged actions.      The district
    court’s grant of summary judgment for Counterclaim Defendants on
    Counterclaim Eleven is accordingly affirmed.
    IV.   Conclusion
    For the foregoing reasons, we VACATE the district court’s
    holding that the Signing Fee Note was unconscionable and therefore
    unenforceable as a matter of law, AFFIRM the district court’s denial
    of summary judgment because genuine issues of material fact remain
    as to whether consideration supported the Signing Fee Note, and
    AFFIRM the Judgment as to the CUTPA counterclaim. Without
    intimating a view on Zerez’s counterclaims not raised on appeal, we
    accordingly REMAND to the district court for further proceedings
    consistent with this opinion.
    72