United States Court of Appeals For the First Circuit _____________________

No. 21-1251

DIANE LAWLESS,

Plaintiff, Appellee,

v.

TOWN OF FREETOWN, et al.,

Defendants, Appellants. _____________________

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Indira Talwani, U.S. District Judge] _____________________

Before

Kayatta and Howard, Circuit Judges, and Walker, District Judge. _____________________

Joseph A. Padolsky, with whom Louison, Costello, Condon & Pfaff, LLP was on brief, for appellants. Chip Muller, with whom Muller Law, LLC was on brief, for appellee. _____________________

March 22, 2023 _____________________

 Of the District of Maine, sitting by designation. WALKER, District Judge. The Appellants, three members of the

Town of Freetown Board of Selectmen, ask us to review a summary

judgment order that rejected their affirmative defense of

qualified immunity against Appellee Diane Lawless’s procedural due

process claim. For reasons that follow, we reverse in part the

district court’s summary judgment ruling and remand for further

proceedings.

I.

Plaintiff-Appellee Diane Lawless served as Treasurer of the

Town of Freetown for roughly two years beginning in 2013 and ending

in 2015. Her contract called for a three-year term of employment,

terminable only for cause following a six-month probationary

period. The Town of Freetown is governed by a Board of Selectmen.

The board members took exception to Lawless’s continued tenure,

arranged for her to receive notice of perceived shortcomings,

placed her on administrative leave, and eventually instituted

disciplinary proceedings based on a notice reciting eight charges.

At her termination hearing before the Board, Lawless was

represented by counsel, questioned the Board’s two witnesses, and

addressed the Board on her own behalf. At the conclusion of the

three-day hearing, the Board voted to terminate Lawless’s contract

without deliberation. In connection with the underlying

controversy concerning Lawless’s performance and in the lead up to

the hearing, certain statements were made by the board members

- 2 - that would permit findings of personal bias or prejudgment. The

Town of Freetown affords no further proceeding post-termination.

Lawless filed an action in Bristol County Superior Court

naming as defendants the Town of Freetown and (now former) board

members Lee Baumgartner, Lisa Pacheco, and Paul Sadeck. The

individual board members are the Appellants herein.1 Lawless

included in her complaint a claim alleging deprivation of her right

to procedural due process, citing

, and on that

basis the defendants removed Lawless’s state court action to the

United States District Court for the District of Massachusetts.

In due course, Lawless amended her complaint and the Town and the

board members filed a joint answer to the amended complaint. The

answer recited nine affirmative defenses but omitted any reference

to the doctrine of qualified immunity or immunity in general.

Following the close of discovery, the board members joined

with the Town in seeking summary judgment against Lawless’s due

process claim, contending for their part that the doctrine of

qualified immunity shielded them from Lawless’s § 1983 claim.

Lawless opposed the motion by arguing, in part, that the board

members waived the defense of qualified immunity by failing to

include it in their answer. The board members did not file a reply

memorandum, leaving Lawless’s waiver challenge unopposed. Nor did

1 Lawless also named Freetown’s replacement treasurer, Jessica Thomas, as a defendant in her action. Ms. Thomas is not one of the Appellants in this appeal. - 3 - they file a motion to amend their answer to add the qualified

immunity defense.

The district court called the summary judgment motion for

oral argument on February 26, 2021. In the limited time available

for argument, the parties argued only their respective positions

on the merits of Lawless’s state law libel claim and her due

process claim; they did not address either the board members’

qualified immunity defense or Lawless’s waiver contention.

The district court issued its summary judgment ruling in a

memorandum and order dated March 9, 2021. Lawless v. Town of

Freetown by & through Thomas, No. 18-cv-11089-IT,

(D. Mass. Mar. 9, 2021). In its ruling, the court opted to proceed

directly to the merits of the qualified immunity defense, neither

relying on nor even mentioning the waiver argument. Based on its

discussion of the merits of the procedural due process claim, which

it found supported on the summary judgment record, the court

quickly rejected the board members’ argument for qualified

immunity, concluding that it is clearly established that a “sham”

disciplinary hearing does not satisfy due process.

The board members (“Appellants”) filed a timely notice of

appeal in which they argued that the district court erred in its

denial of their qualified immunity defense.

- 4 - II.

This Court has jurisdiction over the Appellants’

interlocutory appeal of the district court’s “denial of summary

judgment on qualified immunity only insofar as the appeal rests on

legal, rather than factual grounds.” McCue v. City of Bangor,

(1st Cir. 2016) (cleaned up). Here, the district court

concluded that the facts viewed in the light most favorable to

Diane Lawless would permit a jury to find that the Appellants

violated clearly established constitutional law. That legal

determination is subject to appellate review.

A.

Because Lawless’s waiver argument logically precedes analysis

of the merits, we pause to consider it before turning to the

district court’s qualified immunity ruling. The Appellants did

not assert in their answer the affirmative defense of qualified

immunity. Lawless argued in her summary judgment opposition that

the failure to timely plead the defense amounted to waiver. The

Appellants did not file a reply to that challenge. Nor did they

seek leave to amend their answer.

As an affirmative defense, qualified immunity can be waived

or, more precisely here, forfeited.2 Guzmán-Rivera v. Rivera-

2“Although jurists often use the words interchangeably, forfeiture is the failure to make the timely assertion of a right; waiver is the intentional relinquishment or abandonment of a known right.” Kontrick v. Ryan,

, 458 n.13 (2004) (cleaned up). - 5 - Cruz,

(1st Cir. 1996); Buenrostro v. Collazo,

(1st Cir. 1992). Rule 8 of the Federal Rules of Civil

Procedure provides: “In responding to a pleading, a party must

affirmatively state any avoidance or affirmative defense.” Fed.

R. Civ. P. 8(c). This Court has warned practitioners “that

affirmative defenses not included in an appropriate responsive

pleading are waived,” Carrasquillo-Serrano v. Mun. of Canovanas,

, 42–43 (1st Cir. 2021), and has reversed district

courts for failing to observe this maxim, see, e.g., Knapp Shoes,

Inc. v. Sylvania Shoe Mfg. Corp.,

(1st Cir.

1994). Ordinarily, as explained in Knapp Shoes, “affirmative

defenses under Rule 8(c) must be pled in the answer . . . to give

the opposing party notice of the defense and a chance to develop

evidence and offer arguments to controvert the defense.”

Despite this otherwise stern admonition, in Knapp Shoes this

Court reserved the issue of whether a district court may excuse a

failure to plead “if ‘a plaintiff receives notice of an affirmative

defense by some means other than pleadings’ and is not prejudiced

by the omission of the defense from the initial pleading.”

(quoting Moore, Owen, Thomas & Co. v. Coffey,

(6th Cir. 1993)).3 Since Knapp Shoes, this Court has articulated

3 Another exception applies when the merits of an affirmative defense have been “fully tried under the express or implied consent of the parties, as if it had been raised in the original responsive pleading.” Fed. Deposit Ins. Corp. v. Ramirez-Rivera,

(1st Cir. 1989). - 6 - the standard to allow a district court to excuse a failure to

timely plead where (1) “the defendant asserts [the affirmative

defense] without undue delay and the plaintiff is not unfairly

prejudiced by any delay,” or (2) “the circumstances necessary to

establish entitlement to the affirmative defense did not obtain at

the time the answer was filed.” Davignon v. Clemmey,

(1st Cir. 2003).

If there is an exception to Rule 8(c)’s pleading requirement

in this case, it necessarily falls under the first category, which

calls for consideration of delay and its more significant

counterpart, resulting prejudice. In short, the party seeking to

assert the defense should explain why and the district court should

consider whether the totality of the relevant circumstances (e.g.,

the nature of the case, case pleadings, discovery initiatives,

correspondence, and statements made in open court) supports “a

practical, commonsense” conclusion that “Rule 8(c)’s core purpose-

-to act as a safeguard against surprise and unfair prejudice--has

been vindicated.” Williams v. Ashland Eng’g Co., Inc.,

(1st Cir. 1995), abrogated on other grounds by Carpenters

Local Union No. 26 v. U.S. Fidelity & Guar. Co.,

(1st

Cir. 2000).

- 7 - Given the Appellants’ delay in raising the defense of

qualified immunity and their failure to defend that delay4, the

district court in its discretion could have deemed the defense

forfeited for purposes of summary judgment. The district court,

however, opted not to rely on any waiver or forfeiture. On appeal,

Lawless fails to argue either that the district court abused its

discretion in so proceeding or that that she was prejudiced by any

delay in raising the defense. Accordingly, like the district

court, we proceed to the merits.

B.

We review a district court's denial of summary judgment on

qualified immunity grounds de novo. Estate of Rahim by Rahim v.

Doe,

, 410 (1st Cir. 2022). However, we credit the

district court’s factual assessment that the record, viewed in the

light most favorable to Lawless, the nonmoving party, would support

the finding that the Appellants were seriously biased against her

continued employment by the Town. See Valdizán v. Rivera-

Hernandez,

(1st Cir. 2006). Nonetheless, “we

4Citing Guzmán-Rivera v. Rivera-Cruz,

(1st Cir. 1996), Appellants argue that a state actor is always free to raise the qualified immunity defense “in a post-discovery summary judgment motion even if it was not raised as an affirmative defense in the answer.” Reply Br. 1. However, the defendants in Guzmán-Rivera had asserted the qualified immunity defense in their answer, unlike the Appellants.

. Thus, contrary to Appellants’ argument, Guzmán-Rivera is not a license for defendants to raise initially and exclusively by summary judgment motion a qualified immunity defense. - 8 - remain free to examine, on an interlocutory appeal, whether [a]

fact makes any cognizable legal difference.”

Diane Lawless contends that the appellants violated her right

to due process of law because they harbored biases against her yet

still presided at the only due process hearing afforded to her by

the Town of Freetown. For their part, the Appellants argue they

are entitled to qualified immunity because they provided Lawless

a fulsome, three-day, pretermination process replete with notice

of the charges and possible consequences, the opportunity to cross-

examine and call witnesses, and the opportunity to respond and

advocate for herself, both in her own words and through the closing

argument of counsel. They argue that they are shielded by

qualified immunity because no reasonable board member would

appreciate that this kind of process was deficient, even if the

decisionmakers arrive at the hearing predisposed to terminate the

employee.

The district court rejected the idea that biased decision

makers might provide adequate pretermination procedural due

process based on its determination that the facts viewed in the

light most favorable to Lawless would permit a jury finding “that

the Board had made up its mind to terminate Lawless prior to the

hearing and that no evidence she presented would have changed the

result.” Mem. & Order at 20. Among other facts shedding light on

this ruling, the district court noted several disparaging comments

- 9 - that the Appellants made prehearing, one board member’s remark

that the due process proceeding was a “dog and pony show” standing

in the way of Lawless’s prompt termination, and the Appellants’

failure to deliberate before voting to terminate Lawless’s

contract. In the district court’s estimation, such findings would

support a verdict that Lawless had not received a “true”

opportunity to respond,

in violation of clearly established

law. For the reasons that follow, we conclude that the district

court erred in its assessment of the Appellants’ qualified immunity

defense.

When government officials are sued in their individual

capacities for money damages, the doctrine of qualified immunity

shields them from pecuniary liability unless their conduct

violated “clearly established statutory or constitutional rights

of which a reasonable person would have known.” Pearson v.

Callahan,

(2009). To assess an official’s bid

for qualified immunity, we may begin by determining whether the

conduct in question violated a federal statutory or constitutional

right. Alternatively, we may begin by determining whether the

unlawfulness of the conduct was clearly established at the time.

Punsky v. City of Portland,

(1st Cir. 2022).

The latter inquiry has “two related aspects,” Rocket Learning,

Inc. v. Rivera-Sanchez,

(1st Cir. 2013), namely: (1)

the relative clarity of the governing law to a reasonable official

- 10 - on the date of the alleged wrong and (2) whether the specific

characteristics of the situation confronted by the official would

have made it clear to a reasonable official how the governing law

applied in the given situation. Punsky,

. Together,

these aspects of the inquiry must persuade us that available

precedent placed the legal question beyond debate such that any

reasonable official would have appreciated the illegality of the

conduct in question. City & Cnty. of San Francisco v. Sheehan,

(2015). We take up the latter aspect of the

qualified immunity analysis because it affords the most direct

route to consideration of the clarity of the governing law and

resolution of the appeal.

To begin, the parties do not dispute that Lawless was entitled

under Massachusetts law to due process in connection with the for-

cause termination of her employment contract with the Town of

Freetown. Given this premise, it was clearly established that the

essential components of a pretermination due process hearing were

“oral or written notice of the charges against [her], an

explanation of the employer’s evidence, and an opportunity to

present [her] side of the story.” Cleveland Bd. of Educ. v.

Loudermill,

(1985). It was also clearly

established that “[t]o require more than this prior to termination

would intrude to an unwarranted extent on the government’s interest

in quickly removing an unsatisfactory employee.”

Based on

- 11 - our review of the summary judgment recitation of facts provided by

Lawless and the district court, the pretermination hearing in this

case met all the essential requirements of predeprivation process.

Lawless disagrees because she contends that personal bias

plugged the Appellants’ ears so that they did not actually hear

her response. The district court based its ruling precisely on

this notion. However, as far as the law is concerned, this notion

was drawn a priori by Lawless’s counsel and the district court; it

was not clearly established in the law, at least not in this

circuit and others.

Reasonable persons generally come to understand--

instinctively as much as inductively--that the impartiality of

decisionmakers is a basic precept of a fair process. This Court

has announced as much, stating that “[a]n impartial decisionmaker

is, of course, a fundamental component of due process.” Beauchamp

v. De Abadia,

(1st Cir. 1985) (citing Friendly,

Some Kind of Hearing,

, 1279 (1975)).

Nowhere is this more clearly enshrined in the law than in the

context of judicial and quasi-judicial proceedings. Schweiker v.

McClure,

(1982) (“[D]ue process demands

impartiality on the part of those who function in judicial or

quasi-judicial capacities.”).

Yet, even in judicial proceedings absolute impartiality is

not a constitutional mandate.

- 12 - [V]arious situations have been identified in which experience teaches that the probability of actual bias on the part of the judge or decisionmaker is too high to be constitutionally tolerable. Among these cases are those in which the adjudicator has a pecuniary interest in the outcome and in which he has been the target of personal abuse or criticism from the party before him.

Withrow v. Larkin,

(1975) (footnotes omitted).

However, other than the “constitutionally [in]tolerable”

situations identified by the Withrow Court, “most matters relating

to judicial disqualification [do] not rise to a constitutional

level.” FTC v. Cement Institute,

(1948).

“[M]atters of kinship, personal bias, state policy, remoteness of

interest, would seem generally to be matters merely of legislative

discretion.” Tumey v. Ohio,

(1927); see also

Aetna Life Ins. Co. v. Lavoie,

(1986). Stated

otherwise, even when it comes to judicial officers, the

constitutional threshold for disqualifying personal bias is not

clearly established.

By comparison, the threshold for unconstitutional bias in

pretermination government employment proceedings is about as clear

as mud. In fact, there is not even a basic requirement that

hearing officers be impartial in the employment context.

Chmielinski v. Massachusetts,

(1st Cir. 2008);

Acosta-Sepulveda v. Hernandez-Purcell,

(1st Cir.

1989). To the contrary, it is clearly established that employing

authorities may preside at termination hearings even though they

- 13 - instituted the termination proceedings. Acosta-Sepulveda,

(listing Loudermill entitlements and observing that “it

is not required that a hearing be conducted before an ‘impartial

decisionmaker’”). That kind of bias--essentially a predisposition

to terminate an employee’s contract--is precisely the kind of bias

in play here.5

While this Circuit has openly questioned whether “the issue

of bias can be addressed with an abstract broad statement that the

due process standard of Loudermill either always or never requires

that the hearing officer be unbiased,” Chmielinski,

, such “abstract broad statements”--were they offered--would

not serve as clearly established law for purposes of our qualified

immunity inquiry. See Brosseau v. Haugen,

(2004)

(“It is important to emphasize that this inquiry must be undertaken

in light of the specific context of the case, not as a broad

general proposition.” (internal quotation marks omitted)).

Consequently, the Chmielinski panel’s contemplation of a

decisionmaker “so utterly biased” that the Loudermill response

right can be deemed a hollow exercise,

, does not afford

5 In the context of municipal employment, this species of personal bias is almost certain to be present to a greater or lesser degree. Municipal decisionmakers routinely have a degree of supervisory insight based on observations of workplace performance. To hold that such a bias precludes the town officials from approving a termination even after the employee is given notice and a chance to explain why termination is not called for would be to require most small towns to surrender important responsibilities to persons not accountable to local citizens. - 14 - such clear guidance that any reasonable official in the Appellants’

position would have been on notice that presiding at Lawless’s

termination hearing would violate the due process clause.6

Given that the clear legal statements available in binding

precedent tend more to frustrate than support Lawless’s due process

claim against the Appellants, we have little difficulty concluding

that the doctrine of qualified immunity shields the Appellants

from liability against Lawless’s due process claim. Before ending

our inquiry, we pause to transcribe a coda.

Lawless contends that her case is different because the Town

of Freetown provided only one hearing, a pretermination hearing.

In her understanding, Appellants should have known that a

postdeprivation hearing would be needed if the pretermination

hearing was infected with personal bias, because the availability

6 Concerning the Appellants’ personal liability, clearer guidance is available in this circuit’s precedent, and it does not favor the imposition of liability on individual government decision makers based on bias in a pretermination hearing. Cronin v. Town of Amesbury,

, 260 n.2 (1st Cir. 1996) (“[Cronin] generally argues that the Town defendants were out to get him, and, with respect to the termination specifically, he argues that [the hearing officer] was biased and made evidentiary errors.”); see also

(“Cronin cannot succeed on his procedural due process claim unless he can show that the state failed to provide him with an adequate postdeprivation remedy.”). Cf. Lowe v. Scott,

, 340–41 (1st Cir. 1992) (“[I]f a state provides adequate postdeprivation remedies--either by statute or through the common-law tort remedies available in its courts--no claim of a violation of procedural due process can be brought under § 1983 against the state officials whose random and unauthorized conduct occasioned the deprivation.”).

- 15 - of a state law postdeprivation remedy--be it a breach of contract

claim or a claim for judicial review of administrative action--

does not moot an otherwise ripe, federal procedural due process

claim. The district court took note of the argument but chose not

to address it. Contrary to Lawless’s argument, neither the Supreme

Court nor this Court has clearly established that the membership

of a municipal board that conducts a pretermination proceeding

must, independent of state law, arrange for a postdeprivation

hearing before a neutral official whenever colorable allegations

of bias have been or might be raised against them but the

pretermination hearing otherwise met the full complement of

Loudermill requirements.7

Furthermore, it is not clearly established in this circuit

that postdeprivation remedies available under Massachusetts law

are inadequate to serve as a check against biased pretermination

tribunals that honor Loudermill. While this Court has explained

that a federal claim for a procedural due process violation is not

automatically negated by the availability of a state law breach of

contract claim, see Clukey v. Town of Camden,

(1st Cir. 2013) (collecting cases), in such cases underlying

7Lawless observes that the Appellants did not swear the witnesses, deliberate before voting, or issue findings of fact. However, these attributes were not itemized in Loudermill and Lawless has not identified any within-circuit authority that would require them. In any event, “Ms. Lawless does not contend that any of these, standing alone, [is] dispositive of this instant appeal.” Brief of Appellee at 22. - 16 - process deficiencies were manifest. See, e.g.,

(finding

that the plaintiff did not receive “notice of any kind whatsoever”

(emphasis in original)); Concepcion Chaparro v. Ruiz-Hernandez,

(1st Cir. 2010) (involving a stipulation that no

pretermination process was afforded); Cotnoir v. Univ. of Maine

Sys.,

(1st Cir. 1994) (explaining that the summary

judgment record reflected inadequate notice of both the charges

and the proposed employment consequences and that there was no

predeprivation reveal of the evidence used to justify

termination); Collins v. Marina-Martinez,

(1st

Cir. 1990) (explaining that the plaintiff “had no prior inkling of

what type of information would be requested . . . [;] [n]o

specification of charges . . . [;] no documents available to him[;

and received an] interview last[ing] for 30 minutes”). See also

Loudermill,

(emphasizing the failure to afford the

plaintiffs in the consolidated appeals the opportunity to

respond). In any event, as far as the board-member Appellants are

concerned8, for reasons already explained a violation of clearly

8 Because our appellate jurisdiction is founded on the qualified immunity question, the Town’s potential municipal liability on the due process claim is not before us. We do observe, however, that “[t]he alleged procedural default cannot be the [Board’s] failure to reach the right result. Such a holding would turn any procedural due process claim into a full judicial [or jury] review of discretionary administrative decisions.” Acosta-Sepulveda,

. The district court will need to iron out these concerns based primarily on a review of postdeprivation remedies available under Massachusetts law.

- 17 - established law is not manifested by a genuine issue of personal

bias.9

9 The district court cited contrary law from the Seventh Circuit, specifically Ryan v. Illinois Department of Children & Family Services,

(7th Cir. 1999) (“A plaintiff who can introduce evidence that the decision has already been made and any hearing would be a sham is entitled to go forward with a procedural due process claim.”). While “[t]he Supreme Court has stated that clearly established law can be dictated by controlling authority or a robust consensus of persuasive authority,” Irish v. Fowler,

(1st Cir. 2020), Lawless has not demonstrated to us that the Seventh Circuit’s approach to bias allegations in the procedural due process context is part of a robust consensus of circuit authority, though she has identified simpatico Tenth Circuit authority, citing, inter alia, Bjorklund v. Miller, 467 Fed. App’x 758, 765 (10th Cir. 2012); but see Cacy v. City of Chickasha,

,

, at *5 n.6 (10th Cir. 1997) (Table) (citing Tenth Circuit cases to the contrary). We must also consider divergent views, such as those expressed in McKinney v. Pate,

(11th Cir. 1994) (en banc), in which the Eleventh Circuit held that “the appropriate forum” for allegations of a biased tribunal “is not federal court but a . . . state court possessing the ability to remedy the alleged procedural [bias] defect.”

. The Eleventh Circuit reasoned that the “demonstration that the decisionmaker was biased . . . is not tantamount to a demonstration that there has been a denial of procedural due process [because] procedural due process violations do not become complete ‘unless and until the state refuses to provide due process.’”

at 1562 (quoting Zinermon v. Burch,

(1990)). The Second Circuit appears to concur. See Green v. Dep’t of Educ. of New York,

(2d Cir. 2021) (“Green’s argument that the arbitrator was biased also fails because due process does not require that pre-termination hearings occur before a neutral adjudicator. Even if Green’s pre- termination hearing was imperfect, the availability of a state- court proceeding to challenge the arbitration decision provided a wholly adequate post-deprivation hearing for due process purposes.” (internal quotation marks and citations omitted)). There also appears to be a wider consensus among sister circuits that direct administrative and/or state court postdeprivation review suffices. McDaniels v. Flick,

(3d Cir. 1995); Duchesne v. Williams,

(6th Cir. 1988) (en banc), cert. denied,

(1989); Schaper v. City of Huntsville,

(5th Cir. 1987); see also Riggins - 18 - III.

The district court’s order denying summary judgment on the

federal claims against appellants is reversed, and the case is

remanded for further proceedings.

v. Bd. of Regents of Univ. of Nebraska,

(8th Cir. 1986) (availability of impartial post-termination grievance procedure sufficient to provide procedural due process despite lack of ability for employee to cross-examine adverse witnesses at any stage).

- 19 -