Ames v. Spiegel ( 2021 )


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  •             United States Court of Appeals
    For the First Circuit
    No. 20-1435
    IN RE APPEAL OF BROOKS A. AMES.
    GERALD ALSTON,
    Plaintiff,
    v.
    STANLEY SPIEGEL,
    Defendant, Appellee.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF MASSACHUSETTS
    [Hon. George A. O'Toole, Jr., U.S. District Judge]
    [Hon. M. Page Kelley, U.S. Magistrate Judge]
    Before
    Lynch and Selya, Circuit Judges,
    and Laplante,* District Judge.
    Brooks A. Ames, pro se, for appellant.
    Naomi R. Shatz and Martin R. Rosenthal, with whom David Duncan
    and Zalkind Duncan & Bernstein LLP were on brief, for appellee.
    April 6, 2021
    *   Of the District of New Hampshire, sitting by designation.
    SELYA, Circuit Judge.       Appellant Brooks A. Ames, an
    attorney, challenges an order of the district court imposing a
    sanction against him under Federal Rule of Civil Procedure 11.
    Discerning no abuse of discretion, we affirm.
    I.    BACKGROUND
    We briefly rehearse the relevant facts and travel of the
    case. Ames is a Massachusetts lawyer who represents Gerald Alston,
    a black man who formerly worked as a firefighter.         On December 1,
    2015, Ames brought suit on Alston's behalf against a coterie of
    defendants, including the town of Brookline, Massachusetts (the
    Town), the Town's Board of Selectmen (the Board), and certain
    individuals affiliated with the Town (among them, members of the
    Board, the Town's counsel, and its human resources director).            Of
    particular pertinence for present purposes, Ames named Stanley
    Spiegel as one of the defendants.
    The complaint alleged that Alston's civil rights had
    been infringed in violation of 
    42 U.S.C. §§ 1981
    , 1983, and 1985.
    The   Town   was   alleged   to   have   "maintain[ed]   its   racist   and
    unconstitutional policies by providing the administration wide
    latitude to covertly implement and enforce them."          The Board was
    alleged to have "blocked citizens from exposing and changing the
    Town’s unconstitutional policy."           As to Spiegel, the complaint
    alleged that he was a white resident of Brookline, who served as
    "an elected town meeting member and an appointed member of the
    - 2 -
    advisory committee."1         In addition, the complaint alleged that
    Spiegel had "frequent contact with the Board of Selectmen both
    formally and informally."       It further alleged that a member of the
    Board, Nancy Daly, distributed to the public copies of a "letter
    to the editor" that was about to be published in a local newspaper.
    The letter, which Alston claimed was "more derogatory" than the
    version that was ultimately published, was purportedly authored by
    a retired black firefighter.
    The   complaint    then    alleged      that   the   letter,   which
    "attacked Mr. Alston's courage and credibility," was a means of
    retaliating against Alston.           It went on to allege that, on the
    following day, the newspaper published the letter and Spiegel
    "distributed" copies of the published version to other Town Meeting
    members in order to "provid[e] diversity of opinion" regarding
    Alston's lawsuit.
    In December of 2014 — according to the complaint — the
    Board    retaliated   against    Alston       for   publicly     protesting   his
    1 The complaint offered little information about the status
    of Town Meeting members, but the magistrate judge took judicial
    notice of the fact that the Town has 240 Town Meeting members at
    any given time. See Alston v. Town of Brookline (Alston I), No.
    15-13987, 
    2016 WL 5745091
    , at *16 n.17 (D. Mass. Sept. 30, 2016).
    The record is equally sparse as to the precise nature and function
    of the "Advisory Committee." There is some indication, though,
    that the Advisory Committee is linked to the Town's governmental
    structure and that one of its roles is to approve financial
    settlement agreements to which the Town is a party (including
    settlements of race-discrimination claims).
    - 3 -
    treatment after he had reported a racial slur uttered by a superior
    officer.     Relatedly, the complaint alleged that the Town leaked
    Alston's personnel file to Spiegel and others in an effort to
    "smear" Alston and "undermine his support in the community."             At
    a public meeting, Spiegel allegedly stated that he had access to
    Alston's personnel file in his capacity as a Town Meeting member.
    He also allegedly told a person wearing an "I support Gerald
    Alston" sticker that she would not support Alston if she knew the
    "real story" contained in Alston's personnel file.            In the same
    conversation, Spiegel allegedly represented that he was speaking
    "on behalf of the Town."      Spiegel also claimed (falsely, according
    to the complaint) that two black firefighters had told him that
    they did not support Alston.
    Both the Town and the Board filed motions to dismiss.
    See Fed. R. Civ. P. 12(b)(6).           Ames parried by filing a first
    amended complaint (the FAC) on Alston's behalf.         See Fed. R. Civ.
    P. 15(a)(1)(B).    The amendments, however, neither added new facts
    concerning    Spiegel   nor   altered    the   allegations   against   him.
    Various defendants (including Spiegel) filed motions to dismiss,
    which the district court referred to a magistrate judge.         See Fed.
    R. Civ. P. 73(a).       Spiegel also moved for Rule 11 sanctions,
    asserting, among other things, that Ames had failed to show either
    that the claims against him were grounded in fact or warranted by
    existing case law (or for that matter, by a nonfrivolous argument
    - 4 -
    for extending existing case law).       See Fed. R. Civ. P. 11(b).
    Spiegel specifically noted that it was never alleged that he either
    took "any adverse action against Alston" or that he was "in a
    position to do so."    Indeed, he was not alleged to "have ever met
    or spoken to Alston or interacted in any way with him."     Finally,
    Spiegel pointed out    that even though    the claims against him
    required a showing of "racial animus or invidiously discriminatory
    animus," Alston had not made any such showing.
    After hearing arguments on Spiegel's motion to dismiss,
    the magistrate judge recommended dismissing the claims against
    him.   In her report and recommendation (the 2016 R&R), she advised
    the district   court   to dismiss the   suit against Spiegel with
    prejudice for failure to state a claim upon which relief can be
    granted.   Fed. R. Civ. P. 12(b)(6).     The magistrate judge wrote
    that the claims against Spiegel "would not be solved by clearer
    pleading" because "Spiegel's innocuous actions simply have not
    violated any of Alston's rights."
    Importantly, the 2016 R&R explained in detail the legal
    requirements for each of Alston's claims against Spiegel.    It also
    sent up a red flag, warning that:
    Counsel should be sure when filing another
    complaint   that    there   are    allegations
    sufficient to make out any asserted claims and
    that he plainly states them with regard to
    particular defendants.       By signing the
    pleading, counsel is certifying his belief
    that "the claims, defenses, and other legal
    - 5 -
    contentions are warranted by existing law or
    by a nonfrivolous [legal] argument . . . ."
    Fed. R. Civ. P. 11(b)(2).
    Despite this warning, the 2016 R&R did not address Spiegel's motion
    for sanctions.
    Ames objected to the 2016 R&R.                  On de novo review, see
    Fed.   R.   Civ.   P.    72(b)(3),     the    district        court   overruled   the
    objections       and     adopted     most      of     the     magistrate      judge's
    recommendations.         The exception, though, was the recommendation
    that the claims against Spiegel be dismissed with prejudice.
    Because Alston was granted leave to re-plead his claims against
    all the other defendants, the district court thought "it [was]
    fair to give him a chance to replead his claims against Spiegel."
    Ames proceeded to file a second amended complaint (the
    SAC) on Alston's behalf.           The SAC added a few new allegations with
    respect to Spiegel.         It asserted, in a conclusory fashion, that
    "Spiegel     violated      Mr.      Alston's        rights     by     enforcing   the
    [discriminatory] Policy in concert with                      the Town."      It also
    asserted that "until named as a defendant in this lawsuit," Spiegel
    had acted as an "unofficial surrogate" for the Board by "defending
    [its] conduct publicly and attacking perceived and actual critics
    of the Board and the Town."            For good measure, the SAC asserted
    that   Spiegel     was   "frequently     in    consultation         with   individual
    members of the Board."
    - 6 -
    The SAC also purported to clarify Spiegel's handling of
    the letter to the editor and his confrontation with the Alston
    supporter.       It   alleged   that,   in   the   email    in   which   Spiegel
    distributed the letter, he directed Town Meeting members to a
    quotation from Selectwoman Daly that had appeared in the local
    newspaper which "cautioned about a rush to judgment before more
    facts about [Alston's case] could be made public."                According to
    the SAC, Spiegel noted that he had distributed the letter for "some
    additional insight" and expressed the view that Town Meeting
    members ought not to attack the Town based solely on Alston's side
    of the story.    As a final shot, the SAC alleged that Spiegel became
    "extremely agitated" when he was questioned about his statements
    to the Alston supporter, put his face close to hers, raised his
    voice, shouted "I'm disgusted," and ended the conversation.
    Spiegel again moved both to dismiss and for sanctions.
    The magistrate judge, unswayed by the added allegations, continued
    to recommend that the district court dismiss the claims against
    Spiegel with prejudice.         In her report and recommendation (the
    2017 R&R), she concluded that Alston and his attorney had "largely
    ignored this court's earlier findings as they pertain to defendant
    Spiegel,   and    simply   recycled     portions    of     the   first   amended
    complaint with cosmetic changes."
    Alston objected to this recommendation, but the district
    court adopted it and dismissed with prejudice the claims against
    - 7 -
    Spiegel.     See Alston v. Town of Brookline (Alston II), No. 15-
    13987, 
    2017 WL 1536213
    , at *1 (D. Mass. Apr. 26, 2017).              Despite
    being "provided an opportunity to cure the deficiencies of the
    first amended complaint," the court wrote, Alston had failed.             
    Id.
    The magistrate judge subsequently held a hearing on
    Spiegel's motion for sanctions and ruled that sanctions were in
    order.   As part of her rationale, the magistrate judge stated that
    "the minor changes made from the first to the second amended
    complaint did not make any difference in the viability of the
    claims against Spiegel."         She recognized that the district court
    "reasonably    gave   [Alston]    the   opportunity   to   replead   against
    Spiegel," but declared that such an opportunity was not "a license
    simply to file a frivolous case for the second time."                     Ames
    objected, but the district court agreed that               a   sanction   was
    warranted.    See Alston v. Town of Brookline (Alston III), No. 15-
    13987, 
    2017 WL 3387132
    , at *1 (D. Mass. Aug. 7, 2017).           It ordered
    Ames to pay $20,396.61 as a sanction, concluding that such a dollar
    amount would deter future misconduct.            See Alston v. Town of
    Brookline (Alston IV), No. 15-13987, 
    2019 WL 117605
    , at *1 (D.
    Mass. Jan. 7, 2019).     This timely appeal followed.
    Meanwhile, Alston had appealed the dismissal of his
    claims against Spiegel.     While the instant appeal was pending, we
    affirmed the dismissal of Alston's claims against Spiegel.                See
    Alston v. Spiegel, 
    988 F.3d 564
    , 569 (1st Cir. 2021).
    - 8 -
    II.   ANALYSIS
    Ames complains that the district court blundered by
    "unfairly"     levying   a   sanction     under   circumstances    that   could
    "chill the development of civil rights law."                 He offers three
    contentions in support of this plaint.2             First, he contends that
    Alston's claims against Spiegel had a sufficient factual basis to
    avoid being classified as frivolous.            To buttress this contention,
    he insists that because the district court dismissed the FAC
    without prejudice and allowed Alston to re-plead as to Spiegel,
    the claims could not have been sanctionable.             Second, he contends
    that the claims are anchored in a nonfrivolous argument for the
    extension of existing law. Third, he contends that, in sanctioning
    him for re-pleading the claims against Spiegel, the district court
    treated the magistrate judge's warning (in the 2016 R&R) not merely
    as a red flag but, rather, as "effectively immuniz[ing]" the
    magistrate judge's appraisal of those claims from appeal.
    It   is   apodictic   that    we   review   a   district   court's
    decision to impose Rule 11 sanctions for abuse of discretion.              See
    Protective Life Ins. Co. v. Dignity Viatical Settlement Partners,
    L.P., 
    171 F.3d 52
    , 56 (1st Cir. 1999); Navarro-Ayala v. Nunez, 
    968 F.2d 1421
    , 1425 (1st Cir. 1992).            We have said that an abuse of
    discretion "occurs when a material factor deserving significant
    2   Ames does not challenge the amount of the sanction.
    - 9 -
    weight is ignored, when an improper factor is relied upon, or when
    all proper and no improper factors are assessed, but the court
    makes a serious mistake in weighing them."            Anderson v. Beatrice
    Foods Co., 
    900 F.2d 388
    , 394 (1st Cir. 1990) (quoting Fashion
    House, Inc. v. K Mart Corp., 
    892 F.2d 1076
    , 1081 (1st Cir. 1989)).
    Mindful that sanctions determinations are context-dependent, "our
    review     is     deferential—but      not     reflexively     acquiescent."
    Protective Life, 
    171 F.3d at 56
    .              Consequently, the sanctioned
    party "bears a formidable burden" when attempting to show that the
    sanctioning court abused its discretion.            Navarro-Ayala, 
    968 F.2d at 1425
    .
    Before addressing Ames's contentions, some stage-setting
    is useful.      Under Rule 11, a court may impose sanctions on a lawyer
    "for advocating a frivolous position, pursuing an unfounded claim,
    or filing a lawsuit for some improper purpose."              CQ Int'l Co. v.
    Rochem Int'l, Inc., USA, 
    659 F.3d 53
    , 60 (1st Cir. 2011).            A claim
    is frivolous when it is "either not well-grounded in fact or
    unwarranted by existing law or a good faith argument for an
    extension, modification or reversal of existing law."               Cruz v.
    Savage, 
    896 F.2d 626
    , 632 (1st Cir. 1990).           In determining whether
    a lawyer has offended Rule 11, a court generally must use an
    objective       standard,   asking    what     is   reasonable   under   the
    circumstances.      See 
    id. at 631
    .     Factors to be considered include
    "the complexity of the subject matter, the party's familiarity
    - 10 -
    with   it,   the   time   available   for   inquiry,   and   the    ease   (or
    difficulty) of access to the requisite information."                Navarro-
    Ayala, 
    968 F.2d at 1425
    .        Typically, "some degree of fault is
    required, but the fault need not be a wicked or subjectively
    reckless state of mind; rather, an individual 'must, at the very
    least, be culpably careless to commit a violation.'"                   Roger
    Edwards, LLC v. Fiddes & Son Ltd., 
    437 F.3d 140
    , 142 (1st Cir.
    2006) (quoting Young v. City of Providence ex rel. Napolitano, 
    404 F.3d 33
    , 39 (1st Cir. 2005)).
    It is against this backdrop that we address Ames's
    contentions.
    Ames seeks to find safe harbor in the district court's
    decision to dismiss the FAC without prejudice and its concomitant
    declination to impose sanctions at that time.          In Ames's view, the
    ultimate dismissal of Alston's claims against Spiegel "could not,
    by itself, warrant sanctions unless the claims were frivolous in
    the first place."         This is particularly true, Ames suggests,
    because he "did not disregard a statute or clear First Circuit or
    Supreme Court precedent."
    We agree with Ames's foundational premise:        "[t]he mere
    fact that a claim ultimately proves unavailing, without more,
    cannot support the imposition of Rule 11 sanctions."               Protective
    Life, 
    171 F.3d at 58
    .      Here, however, the case for sanctions goes
    well beyond the mere fact of dismissal.
    - 11 -
    In this instance, the key question is not whether Ames's
    pleading of Alston's claims disregarded a statute or circuit
    precedent directly on point.    Rather, it is whether any reasonable
    attorney, looking at the additional matters pleaded in the SAC,
    "would have believed that he had any evidence to support [his]
    claim[s]" against Spiegel.      Nyer v. Winterthur Int'l, 
    290 F.3d 456
    , 461 (1st Cir. 2002).         The district court answered this
    question in the negative, and so do we.
    The allegations in the FAC, insofar as they pertained to
    Spiegel, chronicled only two events:      his distribution of copies
    of the letter to the editor and his confrontation with the Alston
    supporter.   In the 2016 R&R, the magistrate judge concluded that
    the facts pleaded in the FAC concerning these events "failed to
    state a claim against Spiegel under any actionable legal theory."
    (Emphasis in original).      The magistrate judge further concluded
    that the FAC did not allege any actionable harm resulting from
    either event. After all, the letter had previously been published,
    and Spiegel's comments to the Alston supporter, while unflattering
    to Alston, were non-specific and had no bearing on Alston's
    situation. Nor did the FAC suggest that either of those two events
    were   implicated     in   Alston's   employment   discrimination   or
    retaliation claims.    In point of fact, the claims against Spiegel,
    as pleaded in the FAC, were so wide off the mark that the 2016 R&R
    - 12 -
    warned that the "failure to state a claim would not be solved by
    clearer pleading."
    Notwithstanding this explicit warning, Ames elected to
    try again in the SAC.         As relevant here, that complaint added
    nothing of consequence.3 Nothing in the SAC meaningfully amplified
    Ames's earlier description of Spiegel's conduct and, thus, the SAC
    failed to transmogrify such conduct into actionable misconduct.
    What is more, the SAC — even when read in the light most favorable
    to Alston — failed to forge any link between Spiegel's alleged
    conduct     and   the   adverse    employment    actions   of   which   Alston
    complains (termination of employment and workplace harassment).
    Neither the Town Meeting members nor the Alston supporter are
    alleged to have any connection to Alston's employment.
    The SAC's shortcomings do not end there.           As to Spiegel,
    the   SAC    blithely    ignored     clear,     widely   available   pleading
    requirements for discrimination and retaliation claims.              Take, for
    example, the claims under 
    42 U.S.C. § 1981
    .                 "[S]ection 1981
    3To the extent that the SAC contained new allegations, they
    were nothing more than window-dressing.     Conclusory allegations
    claiming that Spiegel had acted as an unofficial surrogate for the
    Board or had frequently consulted with Board members are not
    entitled to any weight.    See Aulson v. Blanchard, 
    83 F.3d 1
    , 3
    (1st Cir. 1996) (explaining that appellate courts need not credit
    "bald   assertions,   unsupportable    conclusions,   periphrastic
    circumlocutions, and the like" when reviewing the dismissal of a
    complaint). So, too, allegations such as those attributing a state
    of agitation to Spiegel when questioned about his statements to
    the Alston supporter or suggesting that he raised his voice add
    nothing to the Rule 11 calculus.
    - 13 -
    affords relief when racial discrimination precludes a plaintiff
    from       entering       a     contractual         relationship      or     when   racial
    discrimination            impairs      a     plaintiff's      existing        contractual
    relationship."        Spiegel, 988 F.3d at 572.                 Even so, the SAC did
    not    so    much    as       allude   to    the    existence    of    any    contractual
    relationship, let alone allege that Spiegel's conduct impaired
    such a contractual relationship.                     Last — but surely not least —
    the stunning fact is that, in a case about race discrimination,
    the SAC never so much as hinted that Spiegel's actions were
    motivated by racial animus.
    The claims under 
    42 U.S.C. § 1983
     are no less sketchy.
    To make out an equal protection claim under section 1983, Alston
    — at a bare minimum — had to "allege facts indicating that,
    compared      with    others       similarly        situated,    he    was    selectively
    treated" based on his race.                 
    Id. at 574-75
    .      The SAC, however, was
    utterly devoid of any reference to a person or persons similarly
    situated to Alston.               Such a glaring omission evinces either a
    disdain for honoring clearly established law or an ignorance of
    it.    In the same vein, the fact that the SAC failed even to suggest
    (in    a    race-discrimination             case)    that   Spiegel's        actions   were
    motivated by racial considerations indicates culpable carelessness
    on Ames's part.           See Roger Edwards, LLC, 
    437 F.3d at 142
    .
    Pointing to Alston's conspiracy claim under 
    42 U.S.C. § 1985
    , Ames asserts that this claim was not frivolous as against
    - 14 -
    Spiegel because the district court found it viable as against ten
    other defendants.4 That finding, though, does not justify bringing
    a section 1985 claim against Spiegel.           In terms of Rule 11, a
    pleader owes an independent responsibility to each defendant whom
    he chooses to sue.         That a claim may be actionable as to one
    defendant does not excuse bringing that claim against another
    defendant as to whom the claim is obviously baseless.            Cf. Sanchez
    v. Pereira-Castillo, 
    590 F.3d 31
    , 48 (1st Cir. 2009) (explaining
    that, on motion to dismiss, court "must determine whether, as to
    each defendant, a plaintiff's pleadings are sufficient to state a
    claim on which relief can be granted") (emphasis in original).
    Alston's conspiracy claim against Spiegel does not come within a
    country mile of satisfying the Sanchez standard.          Although, Ames
    alleges in his appellate briefing that Spiegel "acted in concert
    with Daly," no such concerted action is alleged in the SAC.               In
    all events, no such allegation was made below.          "If any principle
    is   settled   in   this   circuit,   it   is   that,   absent    the   most
    extraordinary circumstances, legal theories not raised squarely in
    the lower court cannot be broached for the first time on appeal."
    Teamsters, Chauffeurs, Warehousemen & Helpers Union, Loc. No. 59
    v. Superline Transp. Co., 
    953 F.2d 17
    , 21 (1st Cir. 1992).
    4Because we find that this assertion lacks merit, we need
    not consider what effect, if any, it would have on the sanctions
    order if most of Alston's claims against Spiegel were groundless
    but one was not.
    - 15 -
    Ames also argues that, in granting Alston leave to amend
    the    FAC,    the   district       court    "effectively"      sustained    Alston's
    objection to the 2016 R&R.             Building on this slipshod foundation,
    Ames    submits      that    because        that    objection     argued    that   the
    allegations against Spiegel in the FAC stated cognizable claims,
    the district court must have thought that Alston's claims against
    Spiegel were not frivolous.             This is pie in the sky, which melts
    away under the lens of our inquiry.
    The district court made pellucid that it had no wish to
    cut off a litigant's rights prematurely. In this spirit, the court
    thought it "fair" to give Alston another bite at the cherry.
    Alston I, 
    2016 WL 5745091
    , at *1.                  In its brief grant of leave to
    amend, the court did not (either expressly or by implication) adopt
    Alston's objection.          Nor did the court in any way, shape, or form
    suggest       that   it     found     the    claims     against    Spiegel    to    be
    nonfrivolous.        It simply gave Alston (through Ames) an opportunity
    to re-plead if he saw fit.
    Seen in this light, Ames's argument crumbles.                        Even
    though a district court deems a pleaded claim frivolous, it may
    nonetheless give the pleader a chance to re-plead and add facts to
    an amended complaint in order to breathe life into the claim.                      But
    leave to amend does not immunize an attorney who elects to amend
    despite the absence of any nonfrivolous support for the amended
    pleading.      When — as in this case — the pleader avails himself of
    - 16 -
    the opportunity to amend and files a new pleading, he does so at
    his peril and under the watchful eye of Rule 11.         In this respect,
    civil rights cases are no different than other cases, and requiring
    an attorney to abide by the strictures of Rule 11 does not
    impermissibly chill his client's rights.         See Silva v. Witschen,
    
    19 F.3d 725
    , 733 n.15 (1st Cir. 1994) ("[W]e cannot agree that a
    groundless civil rights action is any less appropriate a candidate
    for Rule 11 sanctions than other groundless actions.").
    Ames mounts another line of defense, distilled from the
    text of Rule 11(b).      He notes that the rule provides, in pertinent
    part, that a party's claims may avoid sanctions if they are
    "warranted by existing law or by a nonfrivolous argument for
    extending, modifying, or reversing existing law."         Fed. R. Civ. P.
    11(b)(2).      Overlooking the dearth of factual support for Alston's
    claims against Spiegel, Ames says that those claims were not the
    stuff to which sanctions should attach because they were based
    upon a nonfrivolous argument for the extension of the holding in
    Ray v. Ropes & Gray LLP, 
    961 F. Supp. 2d 344
     (D. Mass. 2013).           We
    do not agree.
    In Ray — a race-discrimination case — the district court
    held   that    an   employer's   dissemination   of   "severely   damaging
    information" about the plaintiff-employee to a media website could
    support a retaliation claim.          
    Id. at 360
    .      There, the Equal
    Employment Opportunity Commission (EEOC) had concluded that there
    - 17 -
    was probable cause to believe that the defendant (a law firm) had
    retaliated against Ray (a lawyer employed as an associate) for
    filing a charge of discrimination with the EEOC.                See 
    id. at 352
    .
    Ray sent the EEOC's findings to a number of people, including then-
    Dean Martha Minow of Harvard Law School.                  See 
    id.
          An online
    publication learned of Ray's correspondence with Dean Minow and
    reached out to the defendant for comment.            See 
    id.
            In response,
    the defendant transmitted Ray's EEOC determination letter to the
    website, which posted it online.          See 
    id.
       The letter contained "a
    recitation of evidence, including detailed information about Ray's
    performance      reviews    and     a     description      of    the    internal
    investigation of Ray and his reprimand by the firm for alleged
    criminal misconduct with a subordinate."            
    Id.
    In denying the defendant's motion for summary judgment
    on Ray's retaliation claim, the district court stated in dictum
    that    "[t]he   threat    of     dissemination     of    derogatory     private
    information, even if true, would likely deter any reasonable
    employee from pursuing a complaint against his employer."                 
    Id. at 360
    .    Attempting to draw an analogy, Ames argues that Spiegel made
    such a threat when he told an Alston supporter that she would not
    back Alston if she knew the "real story" contained in his personnel
    file.    This attempted analogy falls flat.
    As   we   observed     when    we   rejected    Alston's     appeal,
    "Spiegel was neither Alston's employer nor a person alleged to be
    - 18 -
    acting in the employer's stead."5        Spiegel, 988 F.3d at 576.       And,
    moreover, the SAC did not allege what the information in Alston's
    personnel file concerned, nor did it allege that any injurious
    information would come to light at Spiegel's direction.              Finally,
    the SAC never alleged a threat.
    The    short   of   it   is   that   Spiegel   was   not   Alston's
    employer, never disseminated any negative information about Alston
    from Alston's personnel file, and did not threaten any such
    dissemination.    These distinctions create so wide a gulf between
    Ray and the case at hand as to puncture Ames's boast that Alston's
    claims against Spiegel are based on a good-faith argument for an
    extension of Ray.    Put another way, the allegations contained in
    the SAC cannot reasonably be viewed as making a "nonfrivolous
    argument for extending" existing case law.               Fed. R. Civ. P.
    11(b)(2); see Roger Edwards, LLC, 
    437 F.3d at 143
     (affirming Rule
    11 sanctions when deficiencies in appellant's motion "went well
    beyond debatable inference and colorable legal argument").
    We need not linger long over Ames's assertion that he
    cannot be sanctioned for re-pleading the claims in the SAC after
    their original dismissal.      Otherwise, he laments, "[f]ew parties,
    5  The SAC did allege that, on one occasion, Spiegel
    purportedly "represented . . . that he was speaking on behalf of
    the Town." This vague reference, standing alone, does not ground
    a reasonable inference that Spiegel was authorized to act for the
    Town in connection with Alston's employment. See Aulson, 
    83 F.3d at 3
    .
    - 19 -
    even private attorney generals (or their counsel) enforcing civil
    rights laws, are likely to risk payment of up to $20,000 in
    sanctions to preserve appellate rights."            This assertion comprises
    more cry than wool.       It boils down to a claim that, by giving heavy
    emphasis to the magistrate judge's warning that Alston's claims
    against Spiegel "would not be solved by clearer pleading," the
    district court "effectively immuniz[ed]" the magistrate judge's
    appraisal from appeal.
    On this point, Ames relies namely on our decision in
    Hill   v.   State    Street   Corp.,   
    794 F.3d 227
        (1st   Cir.   2015).
    Specifically, he embraces the Hill court's admonition that it is
    important to "protect[] against the possibility that a district
    court could effectively immunize its decisions from review by
    declaring any appeal frivolous."          
    Id. at 230
    .
    Ames's reliance on Hill is mislaid.            The facts of Hill
    are quite different — that case involved a requirement for an
    exorbitant bond as an adjunct to the right to appeal, see 
    id.
     at
    229 — and the case is readily distinguishable.               More importantly,
    the claims against Spiegel are frivolous not because the magistrate
    judge predicted as much in the 2016 R&R but because — despite
    having had the benefit of a warning that the allegations against
    Spiegel     failed   to   comply   with   the   most       basic   of   pleading
    requirements — Ames stubbornly persisted in rehashing essentially
    the same claims.
    - 20 -
    The SAC itself is a testament to the frivolousness of
    those claims.     The meager facts that Alston alleged with respect
    to Spiegel were disconnected from the elements of the claims that
    he asserted — so much so that an objectively reasonable lawyer,
    mulling those facts, would necessarily have concluded that Alston
    could not offer any sufficient factual grounding for his claims
    against Spiegel.     In addition, the legal regime that the pleaded
    facts sought to invoke was sufficiently clear that an objectively
    reasonable lawyer, taking stock of those facts, would necessarily
    have concluded that Alston had no nonfrivolous basis in law for
    his claims.     These conclusions in no way depend either upon the
    magistrate judge's earlier appraisal or upon her warning — but
    that warning put Ames on notice that reiterating the claims,
    without any meaningful augmentation, would be culpably careless
    and, thus, land him in legal quicksand.          See, e.g., Henderson v.
    Dep't of Pub. Safety & Corr., 
    901 F.2d 1288
    , 1294-95 (5th Cir.
    1990); Collins v. Walden, 
    834 F.2d 961
    , 965-66 (11th Cir. 1987).
    To say more would be to paint the lily.            We conclude
    that   the   district   court   acted   well   within   the   ambit   of   its
    discretion when it found that Ames — even on his third try and in
    the face of explicit warnings — ignored obvious factual gaps and
    clear legal requirements in naming Spiegel as a defendant in the
    SAC.   The ensuing sanction was adequately supported both in the
    facts and in the law.
    - 21 -
    III. CONCLUSION
    We respect a lawyer's zealous advocacy for his client.
    But that zeal, in turn, must respect the boundaries of appropriate
    advocacy.   Here, Ames persisted in pursuing claims against Spiegel
    without an adequate basis in fact or in law despite a pointed
    warning from the magistrate judge.         When — as in this case —
    zealous advocacy is based on nothing more than a wing and a prayer,
    it is sanctionable.
    We need go no further. For the reasons elucidated above,
    the sanctions order is
    Affirmed.    Costs to appellee.
    - 22 -