City of Cambridge Retirement v. Ersek ( 2019 )


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  •                                                                                FILED
    United States Court of Appeals
    PUBLISH                                Tenth Circuit
    UNITED STATES COURT OF APPEALS                       April 16, 2019
    Elisabeth A. Shumaker
    FOR THE TENTH CIRCUIT                          Clerk of Court
    _________________________________
    CITY OF CAMBRIDGE RETIREMENT
    SYSTEM; MARTA/ATU LOCAL 732
    EMPLOYEES RETIREMENT PLAN,
    derivatively on behalf of the Western
    Union company,
    Plaintiffs - Appellants,
    and
    STANLEY LIEBLEIN,
    Plaintiff,
    v.                                                        No. 17-1381
    HIKMET ERSEK; JACK M.
    GREENBERG; DINYAR S. DEVITRE;
    RICHARD A. GOODMAN; BETSY D.
    HOLDEN; LINDA FAYNE LEVINSON;
    ROBERTO G. MENDOZA; SOLOMON
    D. TRUJILLO; FRANCES M. FRAGOS
    TOWNSEND; THE WESTERN UNION
    COMPANY, a Delaware corporation,
    nominal defendant,
    Defendants - Appellees.
    _________________________________
    Appeal from the United States District Court
    for the District of Colorado
    (D.C. No. 1:14-CV-00144-MSK-KLM)
    _________________________________
    Jeroen Van Kwawegen of Bernstein Litowitz Berger & Grossmann LLP, New York, New
    York (David J. MacIsaac of Bernstein Litowitz Berger & Grossmann LLP, New York,
    New York; Jeffrey A. Berens of Berens Law LLC, Denver, Colorado; and Michael I.
    Fistel, Jr. of Johnson Fistel LLP, Marietta, Georgia, with him on the briefs), for Plaintiffs-
    Appellants.
    David F. Graham of Sidley Austin LLP, Chicago, Illinois (Hille R. Sheppard of Sidley
    Austin LLP, Chicago, Illinois; and Holly Stein Sollod and Christina Gomez of Holland &
    Hart LLP, Denver, Colorado, with him on the brief) for Defendants-Appellees.
    _________________________________
    Before MATHESON, PHILLIPS, and McHUGH, Circuit Judges.
    _________________________________
    PHILLIPS, Circuit Judge.
    _________________________________
    In this shareholder-derivative action, Shareholders of The Western Union
    Company aver that several of Western Union’s Officers and Directors breached their
    fiduciary duties to the company by willfully failing to implement and maintain an
    effective anti-money-laundering-compliance program (AML-compliance program),
    despite knowing of systemic deficiencies in the company’s AML compliance. The
    Shareholders didn’t make a pre-suit demand on Western Union’s Board of Directors
    to pursue this litigation, and the district court found no evidence that such demand
    would have been futile. The district court thus dismissed the case, reasoning that the
    Shareholders’ obligation to make a pre-suit demand on the Board was not excused.
    Exercising jurisdiction under 
    28 U.S.C. § 1291
    , we affirm.
    BACKGROUND
    Western Union is a public Delaware corporation that facilitates electronic
    money transfers through a sprawling international network of about 550,000
    “agents”—individuals and entities that serve as storefronts where customers can send
    2
    or receive funds—located in over 200 countries and territories. Appellants’ App. vol.
    4 at 854–55, ¶ 14. Western Union’s primary business flows through Western Union
    Financial Services, Inc. (WUFSI), a wholly-owned subsidiary which facilitates
    consumer-to-consumer money transfers. Western Union also offers business-to-
    business and business-to-consumer transfers through another wholly-owned
    subsidiary, Western Union Business Solutions.
    Given its vulnerability to criminal exploitation, the money-transmittal industry
    is heavily regulated. Under the Bank Secrecy Act of 1970 (BSA), 
    31 U.S.C. §§ 5311
    –
    5332, financial institutions—including “money services businesses” like Western
    Union1—must implement and maintain effective AML-compliance programs. See 
    id.
    § 5318(h)(1). At a minimum, these programs must provide for internal controls to
    guard against money laundering, for monitoring and independent compliance testing,
    and for personnel training. See 
    31 U.S.C. § 5318
    (h); 
    31 C.F.R. § 1022.210
    . A money-
    services business with foreign agents must also adopt risk-based approaches to cross-
    border transactions to help “guard against the flow of illicit funds.” 69 F.R. 74439,
    74440 (Dec. 14, 2004). Finally, financial institutions must maintain records and file
    reports on transmittals that exceed certain amounts or are “relevant to a possible
    violation of law or regulation.” 
    31 U.S.C. § 5318
    (g)(1). “Structuring” or breaking
    transactions into smaller denominations to avoid the BSA’s recordkeeping and
    reporting requirements is a crime. 
    Id.
     § 5324.
    1
    A “money services business” qualifies as a “financial institution” under the
    BSA. See 
    31 C.F.R. §§ 1010.100
    (t) & 1010(ff).
    3
    Regulators have long monitored Western Union’s compliance with these
    requirements. Between 2002 and 2006, when Western Union became a public
    company, WUFSI entered into four settlement agreements concerning alleged AML
    violations with federal regulators and state authorities in Arizona, California, and
    New York. Without admitting liability, WUFSI promised to remedy deficiencies in
    its recordkeeping, reporting, and monitoring practices. Yet WUFSI struggled to
    achieve these objectives, and in 2008, it reached a second settlement with Arizona
    regarding alleged recordkeeping violations. A third settlement with Arizona followed
    in 2010: the Southwest Border Agreement (SBA).
    The SBA centered on violations that occurred between 2003 and 2007 at 16
    agent locations in the Southwest Border region—Arizona and the area within 200
    miles north and south of the United States–Mexico border. WUFSI admitted that it
    had “reason to know” that agents at these locations had “knowingly engaged in a
    pattern of money laundering violations that facilitated human smuggling from
    Mexico into the United States through Arizona.” Appellants’ App. vol. 8 at 1933, ¶ 4.
    To remedy these violations, the SBA imposed a $94 million fine and mandated that
    WUFSI work with a court-appointed monitor to improve its AML compliance in the
    Southwest Border region. The SBA set a July 2013 completion deadline for this
    endeavor.
    Three monitors served between 2010 and 2013, recommending a bevy of
    improvements to WUFSI’s AML-compliance program. Western Union struggled to
    keep apace of these mounting proposals, implementing just 18 of (then) 80 proposals
    4
    by September 2011, 33 of 98 proposals by October 2012, and 54 of 98 proposals by
    April 2013. In July 2013—at the end of the initial monitorship—Western Union
    management advised the Board of Directors that certain improvements were “at a
    standstill.” 
    Id.
     vol. 3 at 777–78, ¶¶ 184–85. Management also reported the disturbing
    news that, in the first quarter of 2013, 28 of 335 high-risk agents in the Southwest
    Border region had “confirmed instances of Human Smuggling.” 
    Id. at 786, ¶ 214
    .
    When Western Union failed to complete all the monitors’ proposals by the
    July 2013 deadline, Arizona threatened to declare a willful and material breach of the
    SBA. Instead, recognizing their “mutual goal” that Western Union develop and
    maintain an effective AML-compliance program, the parties negotiated an amended
    SBA, extending the monitorship through December 2017. 
    Id.
     vol. 8 at 1986. The
    Amended SBA also mandated more rigorous recordkeeping and reporting practices
    for transactions in the Southwest Border region.
    As these events unfolded, numerous federal investigations into Western
    Union’s AML compliance began to ramp up. In 2012, the U.S. Attorney’s Office for
    the Central District of California named Western Union a “target” in an investigation
    into a California agent arrested for structuring transactions worth $65.7 million. 
    Id.
    vol. 3 at 763, ¶ 137. Also in 2012, the Federal Trade Commission (FTC) began
    investigating Western Union’s possible facilitation of fraudulent money transfers.
    Two years later, in 2014, the U.S. Attorney’s Office for the Southern District of
    Florida named Western Union a target in an investigation into allegations of money
    5
    laundering by agents in Central America. Meanwhile,2 the U.S. Attorney’s Offices
    for the Eastern and Middle Districts of Pennsylvania started investigating Western
    Union for anti-fraud and AML violations.
    Against this backdrop, various Shareholders filed five derivative actions in
    2014 alleging that certain of Western Union’s Directors had caused the company to
    willfully violate AML laws and regulations. In 2015, the district court consolidated
    these actions, and the Shareholders filed a consolidated complaint, asserting
    violations of the Securities Exchange Act of 1934, breaches of fiduciary duties, and
    Delaware common-law claims. The Directors moved to dismiss under Rule 23.1 of
    the Federal Rules of Civil Procedure, arguing that the Shareholders had failed to
    plead facts sufficient to show the futility of making a pre-suit demand on the Board
    to pursue litigation. The court granted the motion but gave the Shareholders leave to
    amend. Accordingly, on May 2, 2016, the Shareholders filed a first amended
    complaint (FAC), asserting two breach-of-fiduciary-duties claims. The Directors
    again moved to dismiss for failure to plead demand futility.
    While that motion was pending, on January 19, 2017, Western Union entered
    into a deferred prosecution agreement (DPA) with the U.S. Department of Justice and
    the U.S. Attorney’s Offices for the Central District of California, Southern District of
    Florida, and Eastern and Middle Districts of Pennsylvania. The DPA alleged that,
    between 2004 and 2012, Western Union had willfully failed to implement an
    2
    The parties offer no evidence identifying when these investigations began.
    6
    effective AML-compliance program and take corrective action against agents
    engaged in fraud, money laundering, and structuring schemes. Western Union
    admitted these allegations, accepted responsibility, and agreed to penalties and
    conditions in exchange for having criminal charges dismissed after three years. That
    same day, Western Union also announced a settlement with the FTC in a related
    consumer-fraud enforcement action.
    In light of these developments, the district court granted the Shareholders
    leave to amend their pleading. Accordingly, on March 17, 2017, the Shareholders
    filed a second amended complaint (SAC), adding 13 paragraphs addressing the
    settlement agreements. On April 21, 2017, the Directors filed a renewed motion to
    dismiss for failure to plead demand futility, which the district court granted on
    September 29, 2017. This appeal followed.
    ANALYSIS
    The Shareholders concede that they made no pre-suit demand on Western
    Union’s Board of Directors to pursue this litigation. Thus, we need decide only
    whether such demand would have been futile. We first address the standard of review
    applicable to Rule 23.1 dismissals before considering the legal sufficiency of the
    Shareholders’ demand-futility allegations.
    I.    Standard of Review
    Our circuit has yet to decide what standard of review applies to dismissals
    under Rule 23.1 for failure to plead demand futility. See In re ZAGG Inc. S’holder
    Deriv. Action, 
    826 F.3d 1222
    , 1227 (10th Cir. 2016) (finding the standard of review
    7
    immaterial to the decision). The courts of appeals are split on this question, with the
    recent trend favoring de novo review over a discretionary standard.3 We tend to agree
    with the trend towards plenary review, given that the issue whether demand is futile
    depends on the legal sufficiency of the complaint’s allegations—a determination we
    typically review de novo. See Carabajal v. City of Cheyenne, 
    847 F.3d 1203
    , 1212
    (10th Cir. 2017). We see no sound reason to apply a different standard to a derivative
    pleading when we have “exactly the same task as when reviewing the dismissal of
    any other action.” Espinoza v. Dimon, 
    797 F.3d 229
    , 235 (2d Cir. 2015) (explaining
    that an appellate court takes the complaint’s allegations as true and decides whether
    3
    Many circuits historically applied abuse-of-discretion review in derivative
    actions, reasoning that a dismissal for failure to adequately plead demand futility is
    highly fact-intensive. But the more recent trend is to apply de novo review, and at
    least five circuits now use that standard. See, e.g., F5 Capital v. Pappas, 
    856 F.3d 61
    ,
    71 (2d Cir. 2017); Cottrell on behalf of Wal-Mart Stores, Inc. v. Duke, 
    829 F.3d 983
    ,
    990 (8th Cir. 2016); Union de Empleados de Muelles de Puerto Rico PRSSA Welfare
    Plan v. UBS Fin. Servs., 
    704 F.3d 155
    , 162–63 (1st Cir. 2013); Westmoreland Cnty.
    Emp. Ret. Sys. v. Parkinson, 
    727 F.3d 719
    , 724–25 (7th Cir. 2013); McCall v. Scott,
    
    239 F.3d 808
    , 817 (6th Cir. 2001). Still, several circuits have bucked this trend and
    continue to apply a discretionary standard. See, e.g., Louisiana Mun. Police Emps.’
    Ret. Sys. v. Wynn., 
    829 F.3d 1048
    , 1058 (9th Cir. 2016); Freedman v. Redstone, 
    753 F.3d 416
    , 423 (3d Cir. 2014); Kammona v. Onteco Corp., 587 F. App’x 575, 581
    (11th Cir. 2014); Pirelli Armstrong Tire Corp. Retiree Med. Benefits Trust ex rel.
    Fed. Nat’l Mortg. Ass’n v. Raines, 
    534 F.3d 779
    , 783 n.2 (D.C. Cir. 2008).
    8
    they state a claim under the appropriate demand-futility standard).4 We therefore hold
    that dismissals under Rule 23.1 are subject to de novo review.5
    II.   Demand Futility
    Derivative actions empower shareholders to “enforce a corporate cause of
    action against officers, directors, and third parties.” Kamen v. Kemper Fin. Servs.,
    Inc., 
    500 U.S. 90
    , 95 (1991) (quoting Ross v. Bernhard, 
    396 U.S. 531
    , 534 (1970)).
    Because the cause of action belongs to the corporation, shareholders, as a
    “precondition for the suit,” must make a pre-suit demand on the corporation’s board
    of directors to pursue the litigation, “unless excused by extraordinary conditions.” 
    Id. at 96
     (quoting Ross, 396 U.S. at 534). Rule 23.1 requires the complaint to “state with
    particularity” “any effort” to “obtain the desired action from the [corporation’s]
    4
    Notably, some courts of appeals have questioned the logic of deferential
    review in this context—even as precedent binds them to apply it. See, e.g., Israni v.
    Bittman, 473 F. App’x 548, 550 n.1 (9th Cir. Apr. 2, 2012) (“We question whether
    abuse of discretion review is appropriate.”), overruled in part on other grounds by
    Lightfoot v. Cendant Mortg. Corp., 
    137 S. Ct. 553
     (2017); Raines, 
    534 F.3d at
    783
    n.2 (“We tend to agree . . . that an abuse-of-discretion standard may not be logical in
    this kind of case . . . because the question whether demand is excused turns on the
    sufficiency of the complaint’s allegations . . . .”).
    5
    As we noted in In re ZAGG, 826 F.3d at 1227, one of our earlier cases
    suggested that an abuse-of-discretion standard might be appropriate for dismissals
    under Rule 23.1. See deHaas v. Empire Petroleum Co., 
    435 F.2d 1223
    , 1228 (10th
    Cir. 1970) (holding, in assessing demand futility, that nothing in the record “would
    indicate an abuse of discretion”). But in deHaas, the demand-futility question came
    before this court after a full trial, and the issue revolved around a “factual dispute.”
    
    Id.
     Accordingly, deHaas does not prescribe our standard of review when a demand-
    futility issue arises on a motion to dismiss the complaint. See Smith v. United States,
    
    561 F.3d 1090
    , 1098 (10th Cir. 2009) (“The legal sufficiency of a complaint is a
    question of law . . . [that] is reviewed de novo.”).
    9
    directors” and “the reasons for not obtaining the action or not making the effort.”
    Fed. R. Civ. P. 23.1(b)(3). Whether the complaint’s particular allegations suffice
    depends upon the substantive law of the state in which the entity is incorporated—
    here, Delaware. See Kamen, 
    500 U.S. at
    108–09.6
    Because the Shareholders didn’t make a pre-suit demand on Western Union’s
    Board, Rule 23.1 requires that they plead the reasons such demand would have been
    futile under Delaware law. In evaluating the Shareholders’ pleading, we accept as
    true all particularized allegations of fact and give the Shareholders all reasonable
    inferences logically flowing from them. See City of Birmingham Ret. & Relief Sys. v.
    Good, 
    177 A.3d 47
    , 55–56 (Del. 2017). But “conclusory allegations are not
    considered as expressly pleaded facts or factual inferences.” White v. Panic, 
    783 A.2d 543
    , 549 (Del. 2001) (citation omitted).7
    Delaware law employs two tests for demand futility, the application of which
    turns on the nature of the allegations against the board. For allegations that the board
    6
    Rule 23.1 pertains only to the “adequacy of the shareholder representative’s
    pleadings”—it doesn’t “create a demand requirement of any particular dimension.”
    Kamen, 
    500 U.S. at 96
    . Rather, it “clearly contemplates” that such a requirement may
    apply under state substantive law. 
    Id.
    7
    The Shareholders downplay Rule 23.1’s rigorous pleading requirements,
    arguing that the standard is “plaintiff-friendly” and citing numerous Rule 12(b)(6)
    cases to that effect. See Br. for Plaintiffs-Appellants at 38–39. Yet the Rule 23.1
    inquiry is “more onerous” than Rule 12(b)(6). McPadden v. Sidhu, 
    964 A.2d 1262
    ,
    1269 (Del. Ch. 2008). Indeed, Delaware courts often cite Rule 23.1’s particularized-
    pleading standard in contradistinction to the “plaintiff-friendly” standard of Rule
    12(b)(6). See, e.g., Pfeiffer v. Toll, 
    989 A.2d 683
    , 692 (Del. Ch. 2010); In re
    Citigroup Inc. S’holder Derivative Litig., 
    964 A.2d 106
    , 130 n.75 (Del. Ch. 2009).
    10
    acted in violation of its fiduciary duties, demand is excused if a “reasonable doubt”
    exists that (i) the directors are disinterested and independent or (ii) the transaction is
    “otherwise the product of a valid exercise of business judgment.” Aronson v. Lewis,
    
    473 A.2d 805
    , 814 (Del. 1984), overruled on other grounds by Brehm v. Eisner, 
    746 A.2d 244
     (Del. 2000). By contrast, challenges to board inaction require a “reasonable
    doubt” that, when the lawsuit was filed, the board “could have properly exercised its
    independent and disinterested business judgment in responding to a demand.” Rales
    v. Blasband, 
    634 A.2d 927
    , 934 (Del. 1993). The Rales test includes derivative suits
    where “the subject . . . is a violation of the Board’s oversight duties.” Wood v. Baum,
    
    953 A.2d 136
    , 140 (Del. 2008).
    In this case, the Shareholders do not challenge any discrete, affirmative Board
    action. Rather, they claim that the Board willfully failed to implement and maintain
    an effective AML-compliance program despite knowing of systemic deficiencies in
    Western Union’s AML compliance.8 Because this allegation describes inaction, it
    8
    The Shareholders try to shoehorn their claims into the Aronson framework by
    using language evocative of affirmative action. The SAC, for example, characterizes
    this litigation as “aris[ing] from the deliberate decision of Western Union’s board of
    directors . . . to ignore its mandate” to maintain adequate AML-compliance measures.
    Appellants’ App. vol. 3 at 715, ¶ 2. Similarly, on appeal, the Shareholders refer to the
    Board’s “business strategy” to boost profits while “willfully violating” AML laws,
    Br. for Plaintiffs-Appellants at 11–12, and argue that the Board “acted with the intent
    to violate positive law” by “condon[ing] management’s efforts to hamper
    compliance,” Reply Br. for Plaintiffs-Appellants at 19 n.9. Yet the SAC is wholly
    devoid of allegations—particular or otherwise—that the Board was ever informed of
    and affirmatively approved a deliberate course of illegal conduct. See Louisiana Mun.
    Police Emps.’ Ret. Sys. v. Pyott, 
    46 A.3d 313
    , 340–41 (Del. Ch. 2012) (plaintiffs
    must “allege with particularity actual board involvement in a decision that violated
    positive law”), rev’d on other grounds, 
    74 A.3d 612
     (Del. 2013). As the district court
    11
    implicates the Rales test. See Rales, 
    634 A.2d at
    933–34 (observing that Aronson is
    inapposite where the derivative action doesn’t challenge a “business decision”).9
    To prevail under Rales, “a derivative complaint must plead facts specific to
    each director[] demonstrating that at least half of them could not have exercised
    disinterested business judgment in responding to a demand.” Desimone v. Barrows,
    
    924 A.2d 908
    , 943 (Del. Ch. 2007). A director is considered interested10 if filing suit
    would operate to his or her “personal benefit or detriment.” Beam ex rel. Martha
    Stewart Living Omnimedia, Inc. v. Stewart, 
    845 A.2d 1040
    , 1049 (Del. 2004). For
    that reason, a director who is sued may have a disabling interest for pre-suit demand
    explained, the SAC’s allegations reduce to the singular contention that the Board
    “was confronted with deficiencies in . . . management’s conduct as to AML
    compliance” and that it “either condoned the deficiencies or remained consciously
    passive.” Appellants’ App. vol. 8 at 2163. In short, the Shareholders allege failures of
    oversight, not affirmative misconduct.
    9
    In any event, the distinction between Aronson and Rales is immaterial in this
    case because the Shareholders claim that the Directors face liability from suit and are
    therefore incapable of impartially acting on a demand. See Aronson, 
    473 A.2d at 815
    (reasoning that, if the challenged conduct is so “egregious” that it fails the business-
    judgment test, then “a substantial likelihood of director liability” excusing demand
    exists); Rales, 
    634 A.2d at 934
     (excusing demand if the directors’ risk of liability for
    failing to act renders them incapable of exercising their impartial business judgment);
    see also Rosenbloom v. Pyott, 
    765 F.3d 1137
    , 1150 (9th Cir. 2014) (noting that both
    tests excuse demand if the “particularized allegations create a reasonable doubt as to
    whether a majority of the board of directors faces a substantial likelihood of personal
    liability for breaching the duty of loyalty”); In re SAIC Inc. Derivative Litig., 
    948 F. Supp. 2d 366
    , 382 (S.D.N.Y. 2013) (explaining that the two tests “may blur in cases
    like this one” where the risk of personal liability “may also implicate the question
    whether the Board can avail itself of business judgment protections”), aff’d sub nom.
    Welch v. Havenstein, 553 F. App’x 54 (2d Cir. 2014).
    10
    The Shareholders do not challenge any Director’s independence.
    12
    purposes. Ryan v. Gifford, 
    918 A.2d 341
    , 355 (Del. Ch. 2007). But a director’s mere
    status as a defendant isn’t sufficient to compromise the director’s impartiality. See
    Aronson, 
    473 A.2d at 814
     (rejecting this “bootstrap” argument). Rather, the director
    must face a “substantial likelihood” of personal liability.11 Guttman v. Huang, 
    823 A.2d 492
    , 501 (Del. Ch. 2003).
    Directors owe fiduciary duties of care and loyalty to the corporation and its
    shareholders. Mills Acq. Co. v. Macmillan, Inc., 
    559 A.2d 1261
    , 1280 (Del. 1989).
    Where, as here,12 the corporate charter exculpates directors from liability for duty-of-
    care violations, a “substantial likelihood” of liability requires allegations showing
    that the directors have breached their non-exculpated duty of loyalty. That duty
    entails, as a “subsidiary element,” an obligation to act in good faith. Stone v. Ritter,
    
    911 A.2d 362
    , 370 (Del. 2006). Liability for failure to act in good faith requires
    “qualitatively more culpable” conduct than gross negligence. In re Walt Disney Co.
    11
    The Shareholders misstate this standard, asserting that demand is excused if
    a “reasonable doubt” exists that the Directors face “potential liability.” Br. for
    Plaintiffs-Appellants at 3, 8–9, 35, 47, 50. In essence, they argue that the necessary
    quantum of liability risk is anything more than zero. Yet a “mere threat of personal
    liability . . . is insufficient to challenge either the independence or disinterestedness
    of directors.” Aronson, 
    473 A.2d at 814
    . Instead, a “reasonable doubt” as to directors’
    impartiality “should only be found where a substantial likelihood of personal liability
    exists.” Wood, 
    953 A.2d at
    141 n.11 (citation omitted).
    12
    Western Union’s charter exculpates its Directors from liability “for breach
    of fiduciary duty . . . to the fullest extent permitted by Delaware law.” Appellants’
    App. vol. 7 at 1872. Delaware law permits exculpation from monetary liability for
    breach of the duty of care but not for breach of the duty of loyalty. 
    Del. Code Ann. tit. 8, § 102
    (b)(7). Accordingly, Western Union’s charter exculpates liability only for
    duty-of-care violations.
    13
    Deriv. Litig., 
    906 A.2d 27
    , 66 (Del. 2006). Indeed, it requires intentional bad-faith
    conduct, such as acting in pursuit of a disloyal purpose, acting with the “intent to
    violate applicable positive law,” or consciously failing to act “in the face of a known
    duty to act.” Stone, 
    911 A.2d at 369
     (citation omitted).
    Claims alleging failures of board oversight fall within the latter category and
    are considered “possibly the most difficult theory in corporation law upon which a
    plaintiff might hope to win a judgment.” In re Caremark Int’l Inc. Deriv. Litig., 
    698 A.2d 959
    , 967 (Del. Ch. 1996). A Caremark claim requires particularized allegations
    that the board (i) “utterly failed to implement any reporting or information system or
    controls” or (ii) “having implemented such a system or controls, consciously failed to
    monitor or oversee its operations thus disabling themselves from being informed of
    risks or problems requiring their attention.” Stone, 
    911 A.2d at 370
    . Under either
    theory, the directors must have consciously and in bad faith failed to discharge their
    fiduciary obligations. Id.; see also Rich ex rel. Fuqi Int’l, Inc. v. Yu Kwai Chong, 
    66 A.3d 963
    , 980–82 (Del. Ch. 2013) (“The essence of a Caremark claim is a breach of
    the duty of loyalty arising from a director’s bad-faith failure to exercise oversight
    over the company.”).
    Here, the Shareholders don’t appear to allege that Western Union’s Board
    utterly failed to implement any reporting or information systems or controls. Nor
    could they credibly make such an argument, as nearly every settlement that Western
    Union has reached with federal and state authorities since 2002 has acknowledged
    Western Union’s progress towards implementing an effective AML-compliance
    14
    program.13 Instead, the Shareholders seem to argue that the Board consciously failed
    to monitor Western Union’s AML compliance, thereby disabling itself from being
    informed of deficiencies requiring attention.
    To prevail on such a claim under Caremark’s second prong, the Shareholders
    must plead with particularity that the Board was presented with “red flags” alerting it
    to misconduct at the company, see Stone, 
    911 A.2d at 373
    , and that it “consciously
    disregarded” those red flags, see Good, 177 A.3d at 59. Red flags serve as proxies for
    Board knowledge. Hence, the Shareholders must identify “obvious and problematic
    occurrences” supporting an inference that the Board knew of, but consciously
    ignored, material weaknesses in Western Union’s internal AML policies. See Rich,
    
    66 A.3d at 983
    .
    Of course, whether the Board consciously ignored such red flags depends on
    which Board counts for purposes of evaluating demand futility. The Shareholders
    contend that the relevant Board is the 12-member Board that was constituted when
    13
    See Appellants’ App. vol. 7 at 1875 (New York: “[Western Union] has
    undertaken immediate corrective action.”); id. at 1880 (Department of the Treasury:
    “[Western Union] promptly instituted comprehensive national corrective actions . . .
    .”); id. at 1886 (California: “[Western Union] has proactively taken corrective steps .
    . . .”); id. vol. 8 at 1919, ¶ 3 (SBA: “Western Union has developed and implemented
    a risk-based . . . [AML] compliance program.”); id. at 1987, ¶ 2 (amended SBA:
    “Western Union has expended significant resources and has made substantial
    progress in completing the Monitor’s Recommendations.”); id. vol. 4 at 880, ¶ 100
    (DPA: “Western Union took remedial measures and implemented compliance
    enhancements to improve its anti-fraud and anti-money laundering programs.”).
    15
    they filed the FAC in May 2016.14 Meanwhile, the Directors urge us to focus on the
    11-member Board that was in place when the SAC was filed in March 2017.
    Ordinarily, courts assess demand futility based on “the directors in office when
    [the shareholders] initiated [the] action.” Teamsters Union 25 Health Servs. & Ins.
    Plan v. Baiera, 
    119 A.3d 44
    , 57 (Del. Ch. 2015). If the shareholders amend their
    complaint, the relevant board becomes the one in place when the amended complaint
    is filed. See Braddock v. Zimmerman, 
    906 A.2d 776
    , 779 (Del. 2006). But the
    existence of a new board at that time “is relevant to a Rule 23.1 demand inquiry”
    only as to derivative claims in the amended complaint that are “not already validly in
    litigation.” 
    Id. at 785
    .
    The term “validly in litigation” means “a proceeding that can or has survived a
    motion to dismiss.” 
    Id. at 779
    . Claims in an amended pleading meet this definition if
    (i) “the original complaint was well pleaded as a derivative action”; (ii) “the original
    complaint satisfied the legal test for demand excusal”; and (iii) “the act or transaction
    complained of . . . is essentially the same as the act or transaction challenged in the
    original complaint.” 
    Id. at 786
    . The first and second prongs are relevant to whether
    the proceeding survived dismissal, while the third prong examines the continuity
    between the pleadings.
    14
    In their opening brief, the Shareholders appear to argue that the relevant
    Board is the one that was in place when this action first commenced in 2014. In their
    reply brief, however, they argue for the May 2016 Board.
    16
    Here, because the original complaint didn’t survive dismissal, the Rule 23.1
    demand inquiry reset when the Shareholders filed the FAC. See 
    id.
     (“[A] complaint
    that has been dismissed is not validly in litigation.”). The inquiry again reset when
    the Shareholders filed the SAC, at least for derivative claims that weren’t validly
    stated in the FAC. See In re Affiliated Computer Servs., Inc. S’holders Litig., No.
    2821-VCL, 
    2009 WL 296078
    , at *8 (Del. Ch. Feb. 6, 2009) (analyzing whether
    claims in a second amended complaint were validly in the first amended complaint).
    The district court, of course, didn’t dismiss the FAC—the Shareholders filed the SAC
    before it could. But the test for validity also asks whether a claim can survive
    dismissal, and the district court, in dismissing the SAC, explicitly stated that it would
    have dismissed the FAC for failure to plead demand futility. The FAC therefore
    wasn’t valid under Braddock’s second prong.15
    We see no error in this result. When the Shareholders filed the FAC in May
    2016, Western Union’s Board consisted of 12 Directors. Six of those Directors joined
    the Board in 2012 or later, well after most of the red-flag events that the Shareholders
    allege should have alerted the Board to AML-compliance issues—i.e., settlements
    with federal and state authorities between 200216 and 2010. The FAC doesn’t
    15
    The Shareholders insist that the SAC added no additional claims from those
    in the FAC but instead merely “supplemented” the FAC’s well-pleaded allegations.
    Reply Br. for Plaintiffs-Appellants at 20. Yet the continuity between the pleadings
    doesn’t render the FAC valid. The FAC must have also satisfied the legal test for
    demand excusal, and the district court determined that the FAC failed that test.
    16
    Of course, the Directors couldn’t incur liability for failing to act on red flags
    occurring before 2006, when Western Union became a public company. Nonetheless,
    17
    mention the three newest Directors: Jeffrey Joerres (2015), Martin Cole (2015), and
    Robert Selander (2014). As for the other three—Francis Townsend (2013), Richard
    Goodman (2012), and Solomon Trujillo (2012)—the FAC alleges a general
    awareness of systemic deficiencies in Western Union’s AML compliance. But it
    pleads no facts showing that any of those directors consciously disregarded any
    contemporaneous violations of specific requirements imposed by past settlements.
    At most, the FAC alleges that Townsend, Goodman, and Trujillo attended
    numerous meetings at which management17 apprised the Board of setbacks related to
    the ongoing SBA settlement. The FAC asserts that the collective Board remained
    “wholly passive” in the face of these setbacks, see, e.g., Appellants’ App. vol. 3 at
    602, ¶ 9; 
    id. at 688, ¶ 260
    , but it pleads no particularized facts showing how
    Townsend, Goodman, and Trujillo consciously and in bad faith failed to take
    remedial action, see Orman v. Cullman, 
    794 A.2d 5
    , 22 (Del. Ch. 2002) (requiring
    facts specific to the “individual members of th[e] board”). In fact, the FAC’s own
    account suggests that, under these Directors’ oversight, the company improved its
    compliance with the SBA. Compare Appellants’ App. vol. 3 at 645, ¶ 131 (alleging
    the Shareholders seem to allege that these earlier settlements alerted the Board to a
    longstanding pattern of AML violations and structural deficiencies in the company’s
    internal AML-compliance policies.
    17
    The FAC is replete with allegations concerning “management’s” supposed
    resistance to implementing AML-compliance measures in accordance with the SBA.
    But the FAC lacks details about who constituted the “management” team tasked with
    implementing the SBA or why those specific individuals desired to thwart AML
    compliance. We cannot ascribe malicious motives to a nebulous, unnamed group of
    “managers.”
    18
    that one of 91 monitor proposals were complete as of February 2012), with id. at 666,
    ¶ 199 (54 of 98 proposals as of April 2013). Though Western Union didn’t achieve
    full compliance by the July 2013 deadline, the record belies the notion that
    Townsend, Goodman, and Trujillo had wholly abdicated their oversight duties.
    The FAC thus fails to allege that Western Union’s six newest Directors face a
    substantial likelihood of personal liability for consciously disregarding red flags of
    AML noncompliance. To validly state a Caremark claim, then, the FAC must create a
    reasonable doubt about the other six Directors’ impartiality. See Beam, 
    845 A.2d at
    1046 n.8 (explaining that demand to a board with an even number of members is
    futile if at least half are compromised). The FAC doesn’t meet this threshold.
    Aside from the six Directors discussed above, the Board in May 2016 included
    Hikmet Ersek (2010), Jack Greenberg (2006), Betsy Holden (2006), Linda Levinson
    (2006), Roberto Mendoza (2006), and Michael Miles (2006). Even assuming the FAC
    creates a reasonable doubt as to these Directors’ impartiality,18 its allegations about
    18
    Though we needn’t reach the issue, we doubt the FAC states a Caremark
    claim against the remaining six Directors. The FAC avers that the SBA alerted these
    Directors to ongoing AML violations, which they ignored. This mischaracterizes the
    SBA, which concerned past unlawful conduct occurring between 2003 and 2007 and
    not ongoing illegality. In fact, the SBA expressly recognized that, in the years since
    the violations, Western Union had “dedicated substantial resources” to improving its
    AML compliance. Appellants’ App. vol. 8 at 1919, ¶ 3. The SBA thus supports the
    inference that Western Union’s compliance was improving during these Directors’
    tenure on the Board.
    The FAC also alleges failures of oversight related to the SBA, including that
    the Board had permitted management to oppose and thwart the court-appointed
    monitors’ recommendations for improved AML compliance. For example, the FAC
    faults the Board for supporting a disagreement between management and the monitor
    over proposals for front-line associate sign-on controls and background checks. But
    19
    Levinson are immaterial to the demand-futility inquiry. On March 30, 2016, over a
    month before the FAC’s May 2, 2016, filing, Levinson publicly disclosed that she
    would retire as of Western Union’s May 12, 2016, annual meeting. Delaware courts
    have likewise excluded from the inquiry directors who have announced their
    the mere existence of such isolated disagreements over the course of a multi-year
    relationship doesn’t support an inference that management designed to thwart AML
    compliance. More important, the SBA obligated Western Union to collaborate with
    the monitor on AML-compliance issues, not simply to acquiesce to all the monitor’s
    demands. Disagreements over how to approach AML compliance don’t necessarily
    evince bad-faith opposition to AML compliance.
    Similarly, the FAC urges an inference of conscious bad faith based on Western
    Union’s failure to achieve full compliance with the SBA by the July 2013 deadline.
    This ignores that Western Union had implemented a majority of the monitors’
    proposals during the three years of the SBA’s initial iteration. Such substantial
    progress belies the notion that the Board had consciously failed to monitor
    management’s AML-compliance efforts. Presumably, a conscious failure of oversight
    would have resulted in a compliance rate much closer to zero, especially with a
    management team allegedly bent on thwarting such efforts.
    In fact, the FAC details how management routinely reported to the Board on
    implementation progress and setbacks throughout the SBA’s initial term, and how it
    presented plans for addressing open issues—demonstrating a functioning oversight
    system. The FAC emphasizes that early reports exhibited limited progress and that
    “major issues” remained open throughout the initial term. See 
    id.
     vol. 3 at 667, ¶ 205.
    But this portrayal misleadingly omits that the SBA contemplated a three-year period
    for implementation. Partial implementation at the mid-stages of that period suggests
    meaningful efforts at compliance, not bad faith. Indeed, though early reports showed
    sluggish progress, management informed the Board in late 2012 that it was on track
    to full compliance by the July 2013 deadline. The Board properly relied on this
    healthy forecast and allowed management to continue its efforts.
    Ultimately, the insistence on inferring bad faith from Western Union’s failure
    to achieve full implementation by the initial deadline improperly “equate[s] a bad
    outcome with bad faith.” See Stone, 
    911 A.2d at 373
    . Particularized allegations must
    support such an inference, not speculative deduction. The Shareholders’ protestation
    that inferring the Board’s good faith is improper inverts their burden: they must
    proffer particularized facts sufficient to support an inference of bad faith. Such an
    inference doesn’t logically flow from the conclusory allegation that Western Union’s
    failure to achieve compliance stemmed from bad faith.
    20
    impending retirement. See Park Emps.’ Annuity & Benefit Fund of Chicago v. Smith,
    No. 11000-VCG, 
    2016 WL 3223395
    , at *1, *8-11 (Del. Ch. May 31, 2016), aff’d,
    
    175 A.3d 621
     (Del. 2017). As the court in Smith explained, demand futility should be
    determined by reference to “the board that would actually be tasked with determining
    whether or not the corporation will pursue the litigation.” 
    Id. at *9
    .
    The Shareholders attempt to distinguish Smith, arguing that the plaintiffs in
    that case filed a complaint just four days before an uncontested election to replace a
    majority of the directors, who were retiring. They note that here, by contrast, they
    asserted allegations against Levinson in their original complaint in January 2014—
    over two years before she declared her intent to retire. Yet demand futility is assessed
    as of the filing of the complaint that first states valid claims, and the original
    complaint wasn’t valid because it didn’t survive a motion to dismiss. See Braddock,
    
    906 A.2d at 779
    . Thus, assuming, arguendo, the FAC’s validity, the relevant
    comparison is between the FAC’s filing just ten days before Levinson’s retirement
    and the complaint’s filing four days before the directors’ retirement in Smith.
    The Shareholders also highlight that they filed the FAC within 30 days of the
    district court’s order dismissing the original complaint, “a date that was not within
    Plaintiffs’ control.” Reply Br. for Plaintiffs-Appellants at 22. This, too, is irrelevant.
    Levinson’s impending retirement was a matter of public record in Western Union’s
    SEC filings as early as March 30, 2016—well before the Shareholders filed the FAC
    and even before the district court dismissed the original complaint. Regardless of the
    21
    district court’s disposition of the motion to dismiss, the Shareholders had ample
    notice that Levinson would be disabled from considering any litigation demand.
    Thus, excluding Levinson from the analysis, the FAC alleges—at most—that
    five of 11 Directors on the Board at the time of the FAC’s filing risked personal
    liability. Demand to a board with an uneven number of members is futile only if a
    majority is disabled from considering the demand. See Aronson, 
    473 A.2d at 817
    .
    Allegations impugning the impartiality of five of 11 Directors fail to meet this
    threshold, meaning the FAC wasn’t validly in litigation because it would have been
    dismissed for failing to satisfy the “legal test for demand excusal.” See Braddock,
    
    906 A.2d at 786
    .
    The relevant Board for demand-futility purposes, then, is the 11-member
    Board in place when the SAC was filed in March 2017. Yet, with the exception of
    Levinson, the Board in March 2017 was identical to the Board in May 2016, and the
    SAC alleges no additional facts that would render demand to that Board futile. The
    SAC primarily adds allegations concerning the DPA, which addresses criminal AML
    violations that occurred between 2004 and 2012. The SAC seems to allege that the
    Directors as of March 2017 risked personal liability for those violations because they
    all had served for at least part of the period during which the violations occurred. Yet
    the SAC doesn’t particularly allege that the Board was aware of these violations
    when they happened, much less that any individual Director consciously and in bad
    22
    faith had failed to take corrective action.19 Rule 23.1’s rigorous pleading standard
    isn’t satisfied absent particularized allegations as to what each Director knew and
    how they acted on that knowledge.20
    The criminal misconduct that the DPA describes is certainly troubling, but the
    SAC fails to establish that a majority of Western Union’s Board in March 2017 faced
    a substantial risk of personal liability for consciously disregarding that misconduct.
    See Guttman, 
    823 A.2d at 501
    . Thus, because the Board could have impartially acted
    on a pre-suit demand to pursue litigation, we hold that the Shareholders’ obligation to
    make such a demand wasn’t excused. See Rales, 
    634 A.2d at 934
    .
    CONCLUSION
    For the above reasons, we affirm the district court.
    19
    Indeed, the only Director that the SAC purports to connect to the DPA is
    Ersek, and even then, it does so only implicitly. See Appellants’ App. vol. 3 at 801, ¶
    265 (alleging that Western Union admitted its “Chief Executive Officer . . . knew
    about AML violations”).
    20
    The DPA itself doesn’t supply such allegations. It describes how Western
    Union “employees” willfully failed to discipline agents who knew of, but failed to
    address, consumer fraud complaints related to transactions at foreign agent locations.
    Appellants’ App. vol. 4 at 852, ¶ 2. It further describes failures to take corrective
    action against four domestic agents who violated Western Union’s own policies
    against structuring transactions. The DPA doesn’t attribute knowledge of this
    criminal misconduct either to the Board or to any individual Director. Nor does it
    support an inference that the Board consciously disregarded the misconduct. In fact,
    it notes that between 2010 and 2012, Western Union terminated the agents engaged
    in structuring transactions. It also notes that, in the wake of these terminations,
    Western Union undertook “remedial measures and implemented compliance
    enhancements” which demonstrate its “commitment to maintaining and enhancing
    the effectiveness of its compliance program.” Id. at 880, ¶ 100. Such steps hardly
    evince a Board that is consciously blind to AML violations.
    23