Ames v. Spiegel

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

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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).

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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

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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

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 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."

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 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

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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).

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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.

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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

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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.

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 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

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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.

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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

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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.

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 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

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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

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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

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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.

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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.

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 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.

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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.

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