Joseph Allen, IV v. Brown Advisory, LLC ( 2022 )


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  •                               In the
    United States Court of Appeals
    for the Seventh Circuit
    ____________________
    No. 21-1602
    JOSEPH P. ALLEN, IV,
    Plaintiff-Appellant,
    v.
    BROWN ADVISORY, LLC, and BROWN
    INVESTMENT ADVISORY & TRUST COMPANY,
    Defendants-Appellees.
    ____________________
    Appeal from the United States District Court for the
    Southern District of Indiana, Indianapolis Division.
    No. 1:19-cv-4160-RLM-DLP — Robert L. Miller, Jr., Judge.
    ____________________
    ARGUED JANUARY 6, 2022 — DECIDED JULY 20, 2022
    ____________________
    Before SYKES, Chief Judge, and ROVNER and SCUDDER,
    Circuit Judges.
    SYKES, Chief Judge. Joseph Allen granted a financial power
    of attorney to his daughter Elizabeth Key when he and his
    wife experienced declining health and he could no longer
    manage their finances. For several years Key used the power
    of attorney to make withdrawals from Allen’s investment
    accounts held by Brown Advisory, LLC, and Brown Invest-
    2                                                 No. 21-1602
    ment Advisory & Trust Company, two affiliated investment
    firms headquartered in Maryland. Five years later Allen
    revoked the power of attorney and sued the two investment
    companies in Indiana state court raising contract and
    fiduciary-duty claims under Maryland law. He alleged that
    Key’s withdrawals (or some of them) were not to his benefit
    and that the investment companies should not have honored
    them.
    The defendants (collectively “Brown Advisory”) re-
    moved the suit to federal court. After a procedural skirmish
    over whether Key was a necessary party, Allen amended his
    complaint to add his daughter as a defendant. Brown
    Advisory then moved to dismiss the amended complaint.
    The district judge granted the motion, reasoning that the
    investment firm could not be liable for breach of contract
    because the challenged withdrawals were directed by Key
    and authorized by her power of attorney. Regarding the
    fiduciary-duty claim, the judge held that Maryland law does
    not recognize a separate cause of action for breach of fiduci-
    ary duty arising from a contractual relationship. Allen
    moved for leave to amend his complaint again, but the judge
    denied the motion.
    We affirm, though on somewhat different reasoning. The
    judge correctly concluded that the power of attorney shields
    Brown Advisory from liability for breach of contract. But he
    misapprehended Maryland law regarding claims for breach
    of fiduciary duty. Just before he issued his dismissal order,
    the Maryland Court of Appeals clarified that a plaintiff may
    plead a claim for breach of fiduciary duty even when anoth-
    er cause of action (like breach of contract) is available to
    redress the conduct. Plank v. Cherneski, 
    231 A.3d 436
     (Md.
    No. 21-1602                                                  3
    2020). Still, the power of attorney shields Brown Advisory
    from liability for breach of fiduciary duty just as it does for
    breach of contract, so this claim too was properly dismissed.
    Finally, the judge was well within his discretion to deny
    Allen’s motion to file a second amended complaint. The
    deadline for amending the pleadings had expired, so Allen
    had to establish good cause for his late motion. See FED. R.
    CIV. P. 16(b). He did not do so.
    I. Background
    Joseph Allen is a native of Crawfordsville, Indiana, a
    small city northwest of Indianapolis. After graduating Phi
    Beta Kappa from nearby DePauw University in 1959, he
    earned a Ph.D. in physics from Yale University in 1965 and
    embarked on a successful career in the aerospace industry,
    first with NASA’s space program and later with several
    private companies, the last of which was headquartered in
    Arlington, Virginia. He retired in 2004.
    Shortly after retiring, Allen engaged Maryland-based
    Brown Advisory as an investment advisor, executing two
    agreements that are relevant here. Under the first, Allen
    authorized the company to “supervise and direct invest-
    ments” for the assets in his Brown Advisory investment
    accounts. In the second, he established a retirement trust
    account for which Brown Advisory would serve as the
    trustee. As of November 2013, Allen’s IRA accounts with the
    firm were valued at approximately $2.3 million (part of
    about $7.9 million in total assets belonging to Allen and his
    wife as listed in a summary prepared by Brown Advisory).
    In December 2014 Allen and his wife moved to the Grand
    Oaks Assisted Living Community in Washington, D.C. His
    4                                                  No. 21-1602
    wife was experiencing rapidly advancing dementia, and
    Allen—who was suffering from alcoholism and mild cogni-
    tive impairment—could no longer care for her at their home
    in the district.
    A year before this move, Allen had granted a durable
    power of attorney to his daughter Elizabeth Key so she
    could help manage his finances. The July 2013 instrument
    authorized Key to act in Allen’s name for a broad range of
    financial transactions, including those involving financial
    institutions, retirement accounts, trusts, real estate, personal
    and family maintenance, social security, Medicare, and tax
    matters. It also provided that “any third party who receives
    a copy of this document may act under it,” and further
    specified that Allen would indemnify third parties for “any
    claims that arise … because of reliance on this power of
    attorney.”
    In November 2014, a month before he moved to Grand
    Oaks, Allen granted a similarly sweeping but much more
    detailed durable power of attorney to Key, replacing the
    earlier one. Like the 2013 instrument, the 2014 version
    specified that “any third party receiving a duly executed
    copy of this document may rely on and act under it.” The
    2014 power of attorney also contained a similar indemnifica-
    tion clause in which Allen agreed to “indemnify and hold
    harmless any third party from any and all claims because of
    good faith reliance on this instrument.”
    Allen’s condition worsened at Grand Oaks. He attributes
    his decline to actions by the facility’s physicians placing him
    on powerful psychotropic drugs that are not meant for
    patients suffering from active alcoholism. His brother—a
    physician practicing in Louisville—eventually intervened
    No. 21-1602                                                 5
    and took steps to assist his brother in making changes to his
    care. In April 2019 Allen moved from Grand Oaks to
    Wellbrooke of Crawfordsville, an assisted-living facility in
    his Indiana hometown. The physicians at the new care center
    took him off the psychotropic medications, and he commit-
    ted to maintaining his sobriety. With those changes, his
    condition rapidly improved. Later that month he retained
    counsel and granted a new financial power of attorney to his
    brother, revoking the earlier ones he had granted to Key.
    The effectiveness of the revocation was contested, and in
    August 2019 Brown Advisory filed an interpleader action in
    federal court in Maryland in an attempt to settle the dispute.
    We steer clear of that controversy because the events rele-
    vant here occurred during Allen’s time at Grand Oaks, when
    Key’s power of attorney was unquestionably in effect.
    In October 2019 Allen sued Brown Advisory in Indiana
    state court asserting claims under Maryland law for breach
    of contract and breach of fiduciary duty. (All agree that
    Maryland law applies.) Brown Advisory removed the case to
    federal court based on diversity of citizenship. See 
    28 U.S.C. § 1332
    (a). Allen is a citizen of Indiana, the affiliated Brown
    Advisory companies are citizens of Maryland, and the
    amount in controversy exceeds $75,000.
    Following removal, Brown Advisory moved to dismiss
    the action for failure to join Key as a necessary party. See
    FED. R. CIV. P. 12(b)(7). The motion became moot when Allen
    filed an amended complaint adding Key (a citizen of
    Washington, D.C.) as a defendant. Allen and Key have since
    settled, and she is not a party to this appeal.
    6                                                  No. 21-1602
    The chief allegations in the amended complaint concern
    withdrawals from Allen’s accounts at Brown Advisory. He
    alleges that while he was at Grand Oaks, Key used the
    power of attorney to direct the withdrawals, many of which
    were not to his benefit. The challenged transactions include a
    one-time withdrawal of $125,000 as well as regular with-
    drawals of $5,000 ostensibly for “incidental expenses” for
    Allen’s wife. Allen further alleges that the withdrawals
    caused him to incur excess tax penalties of $90,000 per year
    (for at least two years). By the time Allen left Grand Oaks,
    his Brown Advisory IRA accounts were valued at less than
    $600,000.
    Allen additionally alleges that his children sold two of
    his real properties—Key sold one while his son sold the
    other—and did not fully credit the proceeds to his Brown
    Advisory accounts. He claims that the sales occurred “with
    Brown Advisory’s participation,” although he does not
    explain what this participation entailed. Finally, Allen
    alleges that Brown Advisory occasionally declined to take
    his phone calls, failed to provide him with (unspecified)
    “specific information” about his accounts “on multiple
    occasions,” and refused to cover unidentified expenses
    associated with his move to Crawfordsville.
    Brown Advisory moved to dismiss for failure to state a
    claim, see 
    id.
     R. 12(b)(6), arguing that it cannot be liable for
    breach of contract because its actions were taken at Key’s
    direction and in reliance on her power of attorney. The
    power of attorney was attached to the amended complaint,
    and Allen does not dispute that Brown Advisory carried out
    the complained-of withdrawals at Key’s direction. Brown
    Advisory also argued that Maryland does not recognize a
    No. 21-1602                                                7
    claim for breach of fiduciary duty as an independent cause
    of action arising out of a contractual relationship.
    Before the judge ruled on the motion, the Maryland
    Court of Appeals (the state’s highest court) issued an im-
    portant decision clarifying state fiduciary-duty law and
    recognizing breach of fiduciary duty as a stand-alone cause
    of action at law. Plank, 231 A.3d at 466. Especially relevant
    here, the court held that a plaintiff may assert a claim for
    breach of fiduciary duty even when another cause of action
    is available to redress the same conduct. Id. Brown Advisory
    promptly notified the court and Allen of this development
    and sent them a copy of the Plank decision. But Allen rested
    on his original briefing and did not explain the significance
    of Plank to the district court.
    Two months later the judge granted the motion and dis-
    missed the case. On the contract claim, the judge agreed with
    Brown Advisory that Key’s power of attorney shielded the
    company from liability. On the fiduciary-duty claim, he
    accepted the now-obsolete argument that Maryland does not
    recognize a cause of action for breach of fiduciary duty
    arising from a contractual relationship. He did not address
    Plank, apparently overlooking the notice from Brown
    Advisory.
    Allen moved to amend his complaint a second time. His
    proposed second amended complaint sought to implicate
    Brown Advisory in various other financial decisions made
    by him or his family. These include allegations that Brown
    Advisory “did nothing to stop” him from giving a deed of
    gift to his son and that the company improperly handled
    information about an unrelated trust not managed by Brown
    Advisory.
    8                                                   No. 21-1602
    The judge denied leave to amend. First, the motion was
    late. It came six weeks after the deadline to amend the
    pleadings had expired. Rule 16(b)(4) of the Federal Rules of
    Civil Procedure requires “good cause” for a late amendment;
    the judge ruled that Allen had no good excuse for his tardi-
    ness. Alternatively, the judge considered the motion under
    Rule 15(a)(2), the general rule for amending pleadings. As an
    independent ground for denying the motion, he held that
    any further amendment would unduly prejudice Brown
    Advisory.
    II. Discussion
    Allen challenges the dismissal of his amended com-
    plaint—both the contract and fiduciary-duty claims—and
    the denial of his motion to file a second amended complaint.
    The judge’s rulings are subject to different levels of appellate
    scrutiny. We review the dismissal order de novo, accepting
    as true the facts alleged in Allen’s amended complaint and
    drawing all reasonable inferences in his favor. W. Bend Mut.
    Ins. Co. v. Schumacher, 
    844 F.3d 670
    , 675 (7th Cir. 2016). To
    survive a motion to dismiss for failure to state a claim, a
    plaintiff must allege “enough facts to state a claim that is
    plausible on its face.” Bell Atl. Corp. v. Twombly, 
    550 U.S. 544
    ,
    570 (2007). “A claim has facial plausibility when the plaintiff
    pleads factual content that allows the court to draw the
    reasonable inference that the defendant is liable for the
    misconduct alleged.” Ashcroft v. Iqbal, 
    556 U.S. 662
    , 678
    (2009). We review the denial of the motion to amend for
    abuse of discretion. Zenith Radio Corp. v. Hazeltine Rsch., Inc.,
    
    401 U.S. 321
    , 330 (1971); Carroll v. Stryker Corp., 
    658 F.3d 675
    ,
    684 (7th Cir. 2011).
    No. 21-1602                                                   9
    A. Breach of Contract
    To state a claim for breach of contract, Allen had to iden-
    tify a contractual obligation that Brown Advisory owed him
    and a breach of that obligation. RRC Ne., LLC v. BAA Md.,
    Inc., 
    994 A.2d 430
    , 442 (Md. 2010); Taylor v. NationsBank,
    N.A., 
    776 A.2d 645
    , 651 (Md. 2001). The amended complaint
    alleges that Brown Advisory allowed Key to make with-
    drawals from Allen’s accounts that were not ultimately for
    his benefit and increased his tax burden.
    As an initial matter, Allen struggles to identify a contrac-
    tual obligation pertinent to his allegations of breach. He
    points to Brown Advisory’s obligation to “supervise and
    direct investments” in his investment accounts. That provi-
    sion, however, imposes a contractual duty to manage assets
    in Allen’s accounts, not a duty to restrict withdrawals made
    by him or his attorney-in-fact. Allen also notes that the
    company had certain “powers” to manage and protect his
    retirement trust account. But those seem to be just that—
    powers to manage a trust—and not an obligation to restrict
    withdrawals made by those authorized to make them.
    Ultimately, however, the contract claim is foreclosed by
    Key’s power of attorney. A third party generally cannot be
    liable for allowing an action specifically authorized by a
    power of attorney. See Vinogradova v. Suntrust Bank, Inc.,
    
    875 A.2d 222
    , 228 (Md. Ct. Spec. App. 2005), abrogated on
    other grounds by Plank, 
    231 A.3d 436
    ; see also, e.g., Bank IV,
    Olathe v. Capitol Fed. Sav. & Loan Ass’n, 
    828 P.2d 355
    , 364–65
    (Kan. 1992). Here, the power of attorney granted Key the
    authority to make withdrawals from Allen’s accounts. And
    the instrument expressly invited third parties to rely on it by
    10                                                No. 21-1602
    promising to indemnify them for actions taken under and in
    reliance on it.
    Allen argues that Brown Advisory had a duty to assess
    the reasonableness and prudence of Key’s withdrawals
    notwithstanding her power of attorney. No such duty,
    however, is found in any of the relevant contracts. Indeed,
    Key’s power of attorney approved Brown Advisory’s con-
    duct by authorizing Key to withdraw money to the same
    extent that Allen could. See Vinogradova, 
    875 A.2d at 228
    ;
    3 AM. JUR. 2D Agency § 79 (2013) (“A financial institution has
    no duty to determine that the holder of a valid power of
    attorney is not engaging in self-dealing before honoring a
    request for a withdrawal of funds in the name of the princi-
    pal.”). It is true that the company might face liability for
    knowingly assisting Key in perpetrating a fraud against
    Allen or otherwise breaching a duty she owed to him. See
    Bank IV, 828 P.2d at 364–65; RESTATEMENT (SECOND) OF
    AGENCY § 312 (AM. L. INST. 1958). But the first amended
    complaint contains no allegations suggesting that Brown
    Advisory did any such thing. Accordingly, Key’s power of
    attorney shields Brown Advisory from liability for allowing
    the complained-of withdrawals.
    Moving on from the withdrawals, Allen argues that other
    allegations in the first amended complaint state a claim for
    breach of contract. He points first to Brown Advisory’s
    failure to ensure that the proceeds of two real-property sales
    directed by his children were credited to his accounts. This
    does not state a claim for breach of contract because Allen
    has not alleged that the company had any legal duty, let
    alone a contractual duty, with respect to the property sales.
    Indeed, he does not even allege that the properties were
    No. 21-1602                                                11
    under the company’s management and provides only the
    vague remark that the sales occurred “with Brown
    Advisory’s participation.”
    Finally, Allen points to his allegations that Brown
    Advisory occasionally failed to take his calls or provide
    information and refused to cover unspecified expenses
    associated with his move to Crawfordsville. These sparse
    allegations do not support a plausible inference that the
    company breached any contractual obligation. The judge
    properly dismissed Allen’s claim for breach of contract.
    B. Breach of Fiduciary Duty
    Until recently Maryland law pointed in different direc-
    tions about the circumstances under which a plaintiff could
    plead breach of fiduciary duty as a stand-alone cause of
    action. The state’s intermediate appellate court struggled to
    interpret Kann v. Kann, 
    690 A.2d 509
     (Md. 1997), the once-
    leading case on the matter, and sometimes held that a breach
    of fiduciary duty was not cognizable as an independent
    claim for money damages. See, e.g., George Wasserman &
    Janice Wasserman Goldsten Fam. LLC v. Kay, 
    14 A.3d 1193
    ,
    1219 (Md. Ct. Spec. App. 2011).
    In Plank the Maryland Court of Appeals clarified the law.
    The court held that breach of fiduciary duty is a cause of
    action with three elements: (1) the existence of a fiduciary
    relationship; (2) the fiduciary’s breach of a duty owed to the
    beneficiary; and (3) harm to the beneficiary. Plank, 231 A.3d
    at 466. And importantly here, a plaintiff can plead the cause
    of action even when another cause of action, such as breach
    of contract, is available to redress the same conduct. Id. The
    remedies available, however, are limited to those historically
    12                                                   No. 21-1602
    available for the particular type of fiduciary relationship and
    breach at issue. See id. at 466–67.
    As we’ve explained, Plank was decided shortly before the
    judge issued his decision dismissing Allen’s case. Brown
    Advisory brought the opinion to the judge’s attention,
    sending a copy to Allen and the court. But Allen remained
    silent on the import of Plank, and the judge overlooked it.
    Nevertheless, our review is de novo, and we may affirm the
    decision on any ground supported by the record. Jones v.
    Cummings, 
    998 F.3d 782
    , 785 (7th Cir. 2021). Now that
    Maryland’s fiduciary-duty law has been clarified, we apply
    the new understanding to Allen’s claim.
    A fiduciary relationship arises when one party places
    special confidence in another who is bound to act for the
    interest of the first. See Anderson v. Watson, 
    118 A. 569
    , 575
    (Md. 1922); Travel Comm., Inc. v. Pan Am. World Airways, Inc.,
    
    603 A.2d 1301
    , 1320 (Md. Ct. Spec. App. 1992). The amended
    complaint adequately alleges the existence of a fiduciary
    relationship. Allen gave Brown Advisory money to manage
    investments on his behalf, thereby imposing on the company
    the obligation to act for Allen’s benefit within the scope of
    that relationship. See Travel Comm., 
    603 A.2d at 1320
    ; see also
    Green v. H&R Block, Inc., 
    735 A.2d 1039
    , 1048 (Md. 1999)
    (explaining that an agent is a fiduciary to his principal
    within the scope of the agency relationship).
    The difficulty for Allen is alleging a breach of a duty
    within the scope of the fiduciary relationship. A breach
    would surely arise if, for example, Brown Advisory invested
    Allen’s assets for its own benefit in an act of self-dealing. See,
    e.g., SEC v. Cap. Gains Rsch. Bureau, Inc., 
    375 U.S. 180
    , 194
    (1963). The amended complaint does not allege any facts that
    No. 21-1602                                                   13
    suggest self-dealing. Rather, Allen’s chief allegation is that
    the company should not have allowed Key to make certain
    withdrawals from his accounts. As we’ve already explained
    with respect to the contract claim, Key’s power of attorney
    shields Brown Advisory from liability for this conduct.
    Changing the theory of liability to breach of fiduciary duty
    does not expose the company to liability because it had no
    fiduciary obligation to refuse to carry out transactions
    authorized by the power of attorney.
    Allen’s other allegations fare no better under the new
    theory of liability. As to the challenged real-estate sales,
    Allen does not tell us what role Brown Advisory played in
    the sales, nor does he even provide allegations allowing us
    to infer that the properties were within the fiduciary rela-
    tionship. Likewise, the allegations regarding occasional
    failures to communicate and to cover unspecified moving
    expenses are too vague to infer that Allen is entitled to relief.
    The fiduciary-duty claim was properly dismissed.
    C. Motion to Amend the Pleadings
    Allen also challenges the denial of his motion for leave to
    file a second amended complaint. Rule 15(a), the general rule
    for amending pleadings, permits a plaintiff to amend once as
    a matter of course within certain time limits; after that the
    plaintiff must obtain the consent of his adversary or the
    leave of court. FED. R. CIV. P. 15(a). Allen’s motion, however,
    faced an additional hurdle because it came after the deadline
    for amending the pleadings had expired. See 
    id.
    R. 16(b)(3)(A) (providing that the district court must issue a
    scheduling order that limits the time to amend the plead-
    ings). Under Rule 16(b)(4), he had to establish “good cause”
    for the late amendment. A district judge is entitled apply
    14                                                  No. 21-1602
    Rule 16(b)(4)’s heightened standard before turning to
    Rule 15(a); failure to satisfy either rule is fatal to the motion
    to amend. See Alioto v. Town of Lisbon, 
    651 F.3d 715
    , 719 (7th
    Cir. 2011). In this case the judge considered and denied
    Allen’s motion under both Rule 16(b)(4) and Rule 15(a).
    We begin with Rule 16(b)(4), which provides that a party
    seeking to amend the pleadings after the expiration of the
    deadline in the scheduling order must show “good cause”
    for the late amendment. The central consideration in as-
    sessing whether good cause exists is the diligence of the
    party seeking to amend. 
    Id. at 720
    ; Trustmark Ins. Co. v. Gen.
    & Cologne Life Re of Am., 
    424 F.3d 542
    , 553 (7th Cir. 2005); see
    also FED. R. CIV. P. 6(b)(1) (providing that a district court may
    extend a missed deadline for “good cause” when a “party
    failed to act because of excusable neglect”).
    Allen claims that his proposed second amended com-
    plaint was inspired by documents that he had recently
    obtained from his old law firm (a third party to this litiga-
    tion). He received the documents in batches, with the last
    batch arriving about a month before the deadline to amend
    (and more than two months before he moved to amend).
    Allen claims that he needed the time to review and under-
    stand the documents before moving to amend.
    Generally speaking, it is reasonable to conclude that a
    plaintiff is not diligent when he in silence watches a deadline
    pass even though he has good reason to act or seek an
    extension of the deadline. See Bell v. Taylor, 
    827 F.3d 699
    , 706
    (7th Cir. 2016); Adams v. City of Indianapolis, 
    742 F.3d 720
    , 734
    (7th Cir. 2014); Brosted v. Unum Life Ins. Co. of Am., 
    421 F.3d 459
    , 463–64 (7th Cir. 2005). That is what happened here. As
    the deadline to amend approached, Allen received and
    No. 21-1602                                                 15
    reviewed the documents purportedly inspiring his motion to
    amend; yet he did not move to amend or seek an extension
    of the deadline to do so.
    Allen further argues that his lateness should be excused
    because he was locked in discovery disputes with Brown
    Advisory as the deadline approached. That is not a good
    excuse either. Allen’s motion to amend did not rely on any
    documents obtained through discovery, nor does he other-
    wise explain how the discovery disputes frustrated his
    ability to move to amend earlier. Allen provided no good
    excuse for his untimeliness, so the judge’s decision to deny
    the motion under Rule 16(b)(4) was comfortably within his
    discretion.
    Though Rule 16(b)(4) alone justifies the denial of Allen’s
    motion to amend, the judge additionally concluded that the
    motion should be denied under the more lenient standard in
    Rule 15(a)(2), which provides that “[t]he court should freely
    give leave [to amend] when justice so requires.” As the text
    indicates, the rule favors amendment as a general matter. See
    Foman v. Davis, 
    371 U.S. 178
    , 182 (1962). Nevertheless, a
    district court is within its discretion to deny leave to amend
    when it has a “good reason” for doing so, such as futility,
    undue delay, prejudice to another party, or bad-faith con-
    duct. Liebhart v. SPX Corp., 
    917 F.3d 952
    , 964 (7th Cir. 2019).
    Prejudice to the nonmoving party caused by undue delay is
    a particularly important consideration when assessing a
    motion under Rule 15(a)(2). See, e.g., id. at 965; Dubicz v.
    Commonwealth Edison Co., 
    377 F.3d 787
    , 792 (7th Cir. 2004).
    An amended pleading is less likely to cause prejudice if it
    comes without delay or asserts claims related to allegations
    asserted in prior pleadings. See Empress Casino Joliet Corp. v.
    16                                                  No. 21-1602
    Balmoral Racing Club, Inc., 
    831 F.3d 815
    , 832 (7th Cir. 2016).
    Conversely, prejudice is more likely when an amendment
    comes late in the litigation and will drive the proceedings in
    a new direction. See, e.g., McCoy v. Iberdrola Renewables, Inc.,
    
    760 F.3d 674
    , 687 (7th Cir. 2014) (affirming the denial of a
    motion to amend brought at a late stage that introduced new
    theories of liability); Johnson v. Cypress Hill, 
    641 F.3d 867
    ,
    872–73 (7th Cir. 2011) (similar). Such an amendment will
    often require significant discovery on new issues.
    Allen’s proposed second amended complaint sought to
    take the litigation into new factual territory, implicating
    Brown Advisory in various financial decisions made by
    Allen or his family. Those allegations are arguably futile
    because they appear to rest on the questionable assumption
    that the company had a duty to stop decisions made by
    others. In any case, inserting these issues into the case so late
    in the day would have prejudiced Brown Advisory by
    driving the litigation in a new direction as discovery on the
    original issues was nearing completion. Furthermore, once
    the judge issued his dismissal order—which came after the
    deadline for amending the pleadings had passed—Brown
    Advisory withdrew actions it had initiated in other jurisdic-
    tions to enforce subpoenas to uncooperative third parties. If
    the judge had granted Allen’s motion to file a second
    amended complaint, the revived suit would have required
    Brown Advisory to refile those actions.
    Moreover, Allen has not said why he could not have ob-
    tained the documents from his own law firm earlier in the
    litigation. Without any explanation, the proposed second
    amended complaint looks more like an effort to keep Brown
    No. 21-1602                                                  17
    Advisory locked in litigation rather than an understandable
    delay beyond Allen’s control. See McCoy, 760 F.3d at 687.
    Resisting this conclusion, Allen points to our precedents
    explaining that ordinarily a plaintiff whose original com-
    plaint has been dismissed for failure to state a claim should
    be given at least one chance to amend. E.g., Runnion ex rel.
    Runnion v. Girl Scouts of Greater Chi. & Nw. Ind., 
    786 F.3d 510
    ,
    519 (7th Cir. 2015). Amendment is often warranted under
    those circumstances because the dismissal order may reveal
    deficiencies that the plaintiff can rectify with an amended
    pleading, allowing the dispute to be resolved on the merits.
    See, e.g., Bausch v. Stryker Corp., 
    630 F.3d 546
    , 562 (7th Cir.
    2010). Allen’s situation does not fit with those cases, howev-
    er, because he had already amended once and because the
    deadline for amending the pleadings had passed. Adams,
    742 F.3d at 734. It’s also worth noting that the rationale of
    those cases does not apply here because the proposed sec-
    ond amended complaint would have added new theories of
    liability rather than shored up the deficiency of the allega-
    tions in the prior complaint.
    Accordingly, the judge justifiably denied Allen’s motion
    to file a second amended complaint under both Rule 15(a)(2)
    and Rule 16(b)(4). And because Allen’s first amended com-
    plaint failed to state a claim, the judgment of the district
    court is AFFIRMED.