Dalrymple v. Town of Winthrop

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17-P-794 Appeals Court

NANCY DALRYMPLE vs. TOWN OF WINTHROP.

No. 17-P-794.

Suffolk. December 13, 2019. - June 2, 2020.

Present: Sullivan, Maldonado, & Wendlandt, JJ.

Practice, Civil, Summary judgment. Contract, Settlement
agreement, Performance and breach, Construction of
contract. Judgment, Implementing settlement agreement.
Judicial Estoppel.

Civil action commenced in the Superior Court Department on
January 5, 2016.

The case was heard by Robert J. Kane, J., on motions for
summary judgment.

Benjamin Flam for the plaintiff.
Michele E. Randazzo for the defendant.

SULLIVAN, J. The plaintiff, Nancy Dalrymple, appeals from

a summary judgment entered in favor of the town of Winthrop

(town), dismissing her complaint for breach of contract and
2

unjust enrichment.1 On appeal, she contends that the town

committed a breach of a settlement in a Federal court action.

The town maintains that Dalrymple repudiated the settlement

agreement and pursued claims barred by its terms. We conclude

that Dalrymple's delay in signing the settlement for a period of

nearly one year after the agreement was first made, while

litigating claims that were barred by the release, constituted a

repudiation of the agreement as a matter of law. Accordingly we

affirm the entry of judgment in favor of the town.

Background. The matter came before the Superior Court

judge on cross motions for summary judgment. Because judgment

was granted for the town, we review the evidence in the light

most favorable to Dalrymple. See Khalsa v. Sovereign Bank,

N.A., 88 Mass. App. Ct. 824, 830 (2016).

Dalrymple was a police officer employed by the town.2 On

February 8, 2012, Dalrymple filed suit against the town in the

1 Dalrymple's original complaint also contained a count
alleging unfair and deceptive acts, see G. L. c. 93A and G. L.
c. 176D, against Winthrop's insurer, the Massachusetts
Interlocal Insurance Association. The parties later stipulated
to the dismissal of Dalrymple's claims against the insurer.

2 There exists a long history of administrative proceedings
and litigation involving the parties. See Dalrymple v. Civil
Serv. Comm'n, 50 Mass. App. Ct. 611, 612-616 (2000) (detailing
Dalrymple's history as police officer, and harassment and
discrimination she experienced in that position). See also
Dalrymple v. Civil Serv. Comm'n, 82 Mass. App. Ct. 1107 (2012)
(rule 1:28 memorandum and order affirming Civil Service
Commission's ruling upholding police chief's decision to suspend
3

United States District Court for the District of Massachusetts

alleging that the town had violated State and Federal

discrimination laws.3 At the same time, other discrimination and

retaliation claims were pending before the Massachusetts

Commission Against Discrimination (MCAD). In January, 2014, the

MCAD issued a decision favorable to Dalrymple ordering that she

be promoted to sergeant retroactive to March 1, 2002. Dalrymple

v. Winthrop, 36 Mass. Discrimination L. Rep. 10 (2014).

On March 21, 2014, with trial in the Federal case set to

begin ten days later, the parties agreed to settle. Dalrymple's

attorney reported the case settled to the Federal court. The

parties agree that the terms of the settlement required that the

town (1) pay Dalrymple $110,000; (2) offer Dalrymple the ability

to purchase two cemetery plots in town-owned cemeteries; (3)

credit 821 hours of sick leave; and (4) agree that the

settlement would not impact claims Dalrymple might have for

injuries in the line of duty. In exchange, Dalrymple agreed to

Dalrymple for five days for refusing to consent to fitness-for-
duty examination); Dalrymple v. Winthrop, 36 Mass.
Discrimination L. Rep. 10 (2014) (hearing officer determination
that town had discriminated and retaliated against Dalrymple,
ordering that she be promoted to sergeant retroactively to 2002,
and awarding emotional distress damages).

3 Dalrymple amended her complaint on October 26, 2012, and
later filed a second suit against the town based on related
events. The Federal District Court consolidated the two actions
on April 10, 2013.
4

(1) dismiss her Federal court lawsuit and (2) execute a general

release of claims. There is no contemporaneous documentation in

the record regarding the effective date of the release. On

March 24, 2014, the Federal court entered a sixty-day dismissal

nisi order. Dalrymple was sworn in as sergeant on March 31,

2014, in accordance with the MCAD order.

Within one to two days of the promotion, the department

assigned her to the night shift. On April 4, 2014, Dalrymple

and her union filed a grievance alleging that the police chief

had violated the collective bargaining agreement (CBA) by

reassigning Dalrymple to the night shift.

Five days later, counsel for the town sent plaintiff's

counsel a draft release that included all claims through the

date of execution. Dalrymple's attorney sent the town's

attorney a new draft settlement agreement and release on April

17, 2014, with a carve-out from the general release for "[t]he

order that led to Ms. Dalrymple's grievance, filed on April 4,

2014, and any claims or causes of action arising out of the

subject of the April 4, 2014 grievance."4 Although there were e-

mails between attorneys for the town that suggest that they

might have been amenable to the proposal, there is no written

4 The proposed "carve-out" also applied to any possible
claims arising from Dalrymple's ownership of property in
Winthrop.
5

response to this proposal in the record. In the Superior Court,

Dalrymple claimed the town had agreed to the carve-out. The

town attorney's affidavit stated that the parties agreed upon a

release of claims "up until the date plaintiff signed the

release." The town left open at the summary judgment hearing

whether there had been agreement on the carve-out; counsel

stated at the hearing on summary judgment that "[w]e don't think

that there was a carve out, but I can't prove it, and I don't

think [Dalrymple's counsel] can prove it one way or the other,

because there's just no records that show an acceptance of that

term." On appeal, the defendants now agree for purposes of

summary judgment that an agreement on the carve-out was reached,

but the record does not reflect when, if at all, the parties

agreed to the carve-out.5

At some point on or after April 25, 2014, Dalrymple's

counsel informed the town's attorneys that Dalrymple wished to

withdraw from the settlement and wanted "her day in court."

Counsel for the town filed an affidavit stating that he

understood "that Ms. Dalrymple was refusing to sign a release

precisely because she no longer wanted to waive any claims she

5 In the Superior Court Dalrymple claimed the parties had
agreed to the carve-out before she sought to return the case to
the docket. The motion judge treated Dalrymple's assertion that
the carve-out was agreed to as true for purposes of summary
judgment.
6

had against the [t]own and wanted to continue to pursue her

[F]ederal court litigation, despite her prior agreement to the

contrary." A second attorney for the town stated that it was

her understanding that "the source of Ms. Dalrymple's

unwillingness [to sign the release] was because she was upset

about certain actions having occurred with respect to her

employment as a police officer, in particular her shift

assignment."6

On May 9, 2014, Dalrymple sought a thirty-day extension of

the dismissal nisi order, which was granted to June 22, 2014.

Attorneys for Dalrymple and for the town unsuccessfully

attempted to broker a "global settlement" of all pending

disputes. On June 12, 2014, Dalrymple and her union filed a

third grievance alleging that the police chief had violated the

CBA in June, 2014, by preventing her and other sergeants from

bidding on a shift. On June 16, 2014, Dalrymple submitted a

motion to set aside the dismissal nisi order and to restore the

case to the Federal court calendar. In that motion, Dalrymple

stated without further explanation that "[t]he parties' efforts

6 On April 27, 2014, Dalrymple's union also filed a second
grievance on behalf of Dalrymple, two other named officers, and
all other affected union members, alleging that, on April 16,
2014, the police chief had violated the CBA by hiring for a
newly-created position without properly interviewing or
considering qualified candidates, a decision that had the effect
of discriminating against officers who were not white men.
7

to resolve the matter have proven unsuccessful." The town

opposed the motion, arguing that good cause did not exist to

return the case to trial because there had been a settlement

agreement that Dalrymple had refused to sign.7 On June 20, 2014,

the Federal court judge denied Dalrymple's motion to set aside

the order of dismissal nisi, "[b]ecause the parties reported

that the case was settled and this request fail[ed] to give any

reasons why the settlement should be set aside."

On February 18, 2015, Dalrymple filed a new charge with the

MCAD alleging, among other things, that the town's actions

giving rise to her April 4, 2014, and June 12, 2014, grievances

were discriminatory and retaliatory, and that the town had not

given her the same swearing-in ceremony on March 31, 2014, as

other sergeants had received.8

7 In her deposition in this matter, Dalrymple testified that
her reason for refusing to sign the settlement agreement during
that period was that she wanted "[t]o go forward with the trial
in the Federal court. She testified: "[A]t that time when my
counsel went before the court to ask that it be put back on, I
wanted to go forward." In her pro se brief to this court she
says, "[When] I agreed to settle and give a release to the Town
regarding the Federal District Court matter I was not giving
away my future rights regarding any adverse employment actions
the Town would take against me under c. [151B] nor was I bound
to give up my rights under the Collective Bargaining Agreement."
These explanations were not provided to the Federal court when
the motion to restore the case was filed.

8 The MCAD dismissed the complaint on August 10, 2015, for
lack of probable cause.
8

On or about May 7, 2015, counsel for the plaintiff notified

the town that Dalrymple was prepared to execute the release of

claims; counsel for the town replied that there was no longer a

valid agreement. On May 15, 2015, plaintiff's counsel sent a

demand letter to the town, setting out claims of unfair and

deceptive practices arising from the town's failure to honor the

settlement agreement. On June 8, 2015, the town replied,

denying that it had committed a breach of the agreement and

stating that it was Dalrymple who had committed a breach by

failing to execute a release, by attempting to return the

Federal case to trial, and by litigating claims against the town

regarding events arising before the "effective date" of the

settlement agreement.

On June 17, 2015, Dalrymple's counsel sent an executed

agreement and release to the town, dated June 20, 2014, the date

when the Federal district court denied her motion to set aside

the order of dismissal nisi. The signed agreement and release

included the carve-out added by Dalrymple's lawyers in their

April 17, 2014 draft, but added the June 20, 2014 effective

date. The letter accompanying the agreement and release

encouraged the town to sign and implement the settlement.9 It

did not.

9 On July 30, 2015, Dalrymple's counsel made a final attempt
to salvage the settlement. In his letter, counsel stated that
9

Dalrymple then filed suit to enforce the settlement

agreement. On cross motions for summary judgment, a judge of

the Superior Court concluded that Dalrymple had repudiated the

settlement agreement as a matter of law, and the judge entered

judgment for the town. This appeal followed.

Discussion. "We review a grant of summary judgment de novo

to determine whether, viewing the evidence in the light most

favorable to the nonmoving party, 'all material facts have been

established and the moving party is entitled to judgment as a

matter of law.'" Sea Breeze Estates, LLC v. Jarema, 94 Mass.

App. Ct. 210, 215 (2018), quoting Casseus v. Eastern Bus Co.,

478 Mass. 786, 792 (2018). See Mass. R. Civ. P. 56, 365 Mass.

824 (1974). "The moving party bears the burden of affirmatively

demonstrating the absence of a triable issue." Sea Breeze

Estates, LLC, supra, quoting Milliken & Co. v. Duro Textiles,

LLC, 451 Mass. 547, 550 n.6 (2008). "If the moving party

carries its burden, 'the party opposing the motion must respond

and allege specific facts establishing the existence of a

"we concede that [Dalrymple] experienced buyer's remorse and
asked the court to relieve her of the agreement by restoring the
matter to the trial list," but he argued that "[m]atters . . .
remained in limbo until we notified you, in May 2015, that she
was now prepared to go forward with the terms we had negotiated
in 2014." Dalrymple now claims the statement was unauthorized.
The statement is immaterial to our resolution of the case, and
we do not consider it. For the reasons explained infra, it was
Dalrymple's conduct that compels a judgment for the defendant.
10

genuine issue of material fact.'" Sea Breeze Estates, LLC,

supra, quoting French King Realty Inc. v. Interstate Fire & Cas.

Co., 79 Mass. App. Ct. 653, 659-660 (2011).

1. Repudiation, breach, and judicial estoppel. Both

parties contend that the other repudiated a binding agreement.

We first address whether Dalrymple repudiated the agreement when

she sought to return the case to the trial list. We next

consider whether Dalrymple engaged in a material breach of the

agreement when she failed to sign it for a period of one year,

and when she litigated claims arguably covered by the release.

In the course of the latter discussion we also consider whether

the town was judicially estopped from denying the existence of a

binding agreement at the time that Dalrymple tendered the signed

document.

Dalrymple contends that the town committed a breach of a

binding agreement when it refused to perform after she signed

the settlement agreement and release.10 The town maintains that

Dalrymple engaged in a material breach, thus repudiating the

agreement as a matter of law, when she failed to sign a release

and moved to restore the Federal case to the trial docket on

June 16, 2014.

10Dalrymple retained counsel after filing her appellate
brief pro se. New successor counsel filed a reply brief and
appeared at oral argument.
11

"Repudiation by one party relieves the other party from

further performance, but such repudiation 'must be a definite

and unequivocal manifestation of intention [not to render

performance].'" Coviello v. Richardson, 76 Mass. App. Ct. 603,

609 (2010), quoting Hammond v. T.J. Litle & Co., 82 F.3d 1166,

1178 (1st Cir. 1996). We pass on the question whether Dalrymple

showed a "definite and unequivocal manifestation" of her intent

not to perform her obligations under the settlement agreement

when she sought to return the Federal case to trial (citation

omitted). Coviello, supra at 609. The record shows that

plaintiff's counsel reported to the town's counsel two possible

reasons for her motion -- a desire to walk away, or a reluctance

to sign a release that included events occurring after the oral

agreement was reached. However, the release (as originally

drafted by the town) would have required her to waive the April

4, 2014 grievance, and there is no indication in the

contemporaneous record whether the town had agreed to the carve-

out at the time Dalrymple's counsel initially proposed it or at

the time Dalrymple sought to restore the case to the docket.

The timing of any agreement regarding the carve-out may be

material, and because we do not have an adequate record on this
12

factual issue, we decline to address whether summary judgment

could be properly entered on this basis.11

Dalrymple did not execute the agreement and release for

over eleven months after the Federal court ruling, however, and

continued to litigate claims that were covered by the release

she proffered. Therein lies the undisputed fact that commands

the result here. Dalrymple contends that the doctrine of

judicial estoppel bars the town from denying the existence of a

contract that it asserted was binding in Federal court, and that

the town was required to perform its obligations under the

settlement agreement once Dalrymple signed the agreement and

11 Neither party has briefed whether, in an employment
discrimination case, an employer may lawfully insist that
allegedly discriminatory conduct that occurs between the date of
an agreement in principle to settle discrimination claims and
the time the settlement agreement is executed be released by a
general release of claims as of the date of execution. See
generally Warfield v. Beth Israel Deaconess Med. Ctr., Inc., 454
Mass. 390, 397, 398 (2009), abrogated on other grounds by Joule,
Inc. v. Simmons, 459 Mass 88 (2011) (in context of workplace
discrimination claims, "considerations of public policy play an
important role in the interpretation and enforcement of
contracts" and waiver of contractual rights or remedies must be
stated in "clear and unmistakable terms"), cited with approval
in Crocker v. Townsend Oil Co., 464 Mass. 1, 14-15 (2012)
(requiring specificity in releases of statutory wage claims).
The town agrees, for purposes of summary judgment, that it was
willing to agree to a release that included the carve-out for
the April 4, 2014 grievance "and any claims or causes of action
arising out of the subject of the April 4, 2014 grievance." The
record does not indicate when such an agreement was reached, and
the timing of any agreement regarding the carve-out may be
material. On this record, therefore, we decline to address the
matter.
13

release, no matter how long it took her to sign it. The town

maintains that Dalrymple committed a breach of a material term

of the settlement agreement and release by her months-long

refusal to execute it, thus repudiating the contract. On the

basis of the undisputed facts before us, we conclude that the

town is not estopped from arguing that Dalrymple engaged in a

material breach of the agreement when she failed to execute it

for a period of eleven months after the Federal court declined

to reinstate the case to the trial list, thus repudiating the

agreement.

We set forth the law relevant to material breach and

repudiation, as well as the law of judicial estoppel, as our

analysis of these doctrines is interrelated, resting ultimately

on the reasonableness of Dalrymple's extended failure to sign

the agreement and release. "A material breach of contract by

one party excuses the other party from performance as matter of

law." Hastings Assocs., Inc. v. Local 369 Bldg. Fund, Inc., 42

Mass. App. Ct. 162, 171 (1997). "A repudiation of a contract is

a material breach, and '[i]n order to operate as a discharge of

the other party, the repudiation must be either with respect to

the entire performance that was promised or with respect to so

material a part of it as to go to the essence. It must involve

a total and not merely a partial breach." Coviello, 76 Mass.
14

App. Ct. at 609, quoting Bucciero v. Drinkwater, 13 Mass. App.

Ct. 551, 555 (1982).

"[T]wo fundamental elements are widely recognized as

comprising the core of a claim of judicial estoppel. First, the

position being asserted in the litigation must be directly

inconsistent, meaning mutually exclusive of, the position

asserted in a prior proceeding. . . . Second, the party must

have succeeded in convincing the court to accept its prior

position." Holland v. Kantrovitz & Kantrovitz LLP, 92 Mass.

App. Ct. 66, 74 (2017), quoting Otis v. Arbella Mut. Ins. Co.,

443 Mass. 634, 640-641 (2005). "Notwithstanding that general

articulation of the doctrine, there may arise certain instances

where the party's prior position was asserted in good faith, and

where the circumstances provide a legitimate reason -- other

than sheer tactical gain -- for the subsequent change in that

party's position." Holland, supra, quoting Otis, supra at 642.

Assuming, without deciding, that the March, 2014 settlement

agreement (with the April, 2014 carve-out) was enforceable under

a theory of judicial estoppel at or within a reasonable period

of time after the Federal court issued its June 20, 2014 order,

Dalrymple could no longer enforce the settlement agreement and

release some eleven months later because she waited an

unreasonable amount of time to execute it, while simultaneously

litigating claims covered by it.
15

None of the draft agreements included language specifying a

date by which the parties were required to sign. However,

"where a written agreement fails to specify a deadline by which

a contractual obligation or right must be exercised, courts may

infer that the parties intended a 'reasonable' date if this can

be done without changing the essence of the contract." Duff v.

McKay, 89 Mass. App. Ct. 538, 545 (2016), citing Plymouth Port,

Inc. v. Smith, 26 Mass. App. Ct. 572, 575 (1988); Middleborough

v. Middleborough Gas & Elec. Dep't, 47 Mass. App. Ct. 655, 658

(1999). See Lubin & Meyer, P.C. v. Lubin, 427 Mass. 304, 309-

310 (1998); Peterson v. Tremain, 35 Mass. App. Ct. 422, 425

(1993); Charles River Park, Inc. v. Boston Redev. Auth., 28

Mass. App. Ct. 795, 814 (1990) ("in the absence of such a

specific requirement, the time for performance does not extend

forever but only for a reasonable time"). "When, as here, the

facts are undisputed, the question of whether an act was done

within a reasonable time is a question of law for the court."

Middleborough v. Middleborough Gas & Elec. Dep't, 47 Mass. App.

Ct. 655, 658 (1999), citing Stone v. W.E. Aubuchon Co., 29 Mass.

App. Ct. 523, 528 (1990). "What is a reasonable period of time

depends on the nature of the contract, the probable intention of

the parties, and the attendant circumstances." Plymouth Port,

Inc., supra. See Duff, supra; Charles River Park, Inc., supra.
16

In the context of the settlement of the employment dispute

at issue here, delaying the execution of the agreement and

release of claims by over eleven months was unreasonable. 12 The

ongoing employment relationship places a premium on the

certainty associated with a final resolution of claims. The

town negotiated the settlement agreement seeking certainty

regarding its exposure to Dalrymple's claims, and it was denied

an essential and inducing feature of its bargain when Dalrymple

failed to sign the release for nearly one year after the Federal

court denied her motion and after, as Dalrymple claimed in

moving for summary judgment, the parties had agreed to the

carve-out she sought.

The failure to sign the agreement and release in a

reasonable period of time, coupled with the pursuit of

litigation covered by it, constituted a material breach as a

matter of law. "A party to a contract generally is relieved of

[its] obligations under that contract only when the other party

has committed a material breach, that is, 'a breach of "an

essential and inducing feature of the contract[]."'" Duff, 89

Mass. App. Ct. at 547, quoting Lease-It, Inc. v. Massachusetts

12 We do not hold that the passage of eleven months is per
se unreasonable. Rather, given the undisputed facts, it was
here. We likewise do not decide whether the passage of time or
the nature of the covered claims that the plaintiff did litigate
would, on their own, be per se unreasonable.
17

Port Auth., 33 Mass. App. Ct. 391, 396 (1992). "[O]nly a

material breach of a contract . . . justifies a party thereto in

rescinding it." Lease-It, Inc., supra, quoting 6 Williston,

Contracts § 829 (3d ed. 1962).

"Whether a breach is material or immaterial normally is a

question for the jury to decide." Lease-It, Inc., 33 Mass. App.

Ct. at 396, citing 6 Williston, Contracts § 841, at 159. See

EventMonitor, Inc. v. Leness, 473 Mass. 540, 546 (2016)

("Whether a party has committed a material breach ordinarily is

a question of fact"). Nevertheless, if "the evidence on the

point is . . . undisputed . . . the court must intervene and

address what is ordinarily a factual question as a question of

law." EventMonitor, Inc., supra, quoting Teragram Corp. v.

Marketwatch.com, Inc., 444 F.3d 1, 11 (1st Cir. 2006). See

Lease-It, Inc., supra (materiality "normally is a question for

the jury to decide. . . . On this record, however, we may

decide the matter on our own"). The facts are undisputed.

Dalrymple's failure to execute a release of claims in a

reasonable amount of time, together with the ongoing litigation,

was a material breach as a matter of law, because it went to "an

essential and inducing" element of the contract; an end to

litigation and the certainty provided by the release constituted

the essential benefit of the bargain for the town (citation

omitted). Duff, 89 Mass. App. Ct. at 547. Dalrymple repudiated
18

the agreement, and the town was relieved of its obligation to

honor it.

As previously noted, Dalrymple filed a pro se MCAD charge

against the town involving conduct predating what she claims to

be the June 20, 2014 effective date, conduct that was not

included in the carve-out for the April 4, 2014 grievance and

related claims.13 For example, her February 18, 2015 MCAD charge

claimed that the town had retaliated against her by declining to

provide a ceremony and a cake when she was sworn in as a

sergeant on March 31, 2014. These events were not included in

the carve-out for the April 4, 2014 grievance.14 She also

referenced the events that gave rise to the June 12, 2014

grievance regarding a different departmental shift bid. This

claim too predated the June 20, 2014 effective date.

Consequently, Dalrymple's maintenance of the above mentioned

portions of the MCAD charge was also a breach of the settlement

13Contrary to the argument in her reply brief, Equal
Employment Opportunity Commission v. Astra USA, Inc., 94 F.3d
738 (1st Cir. 1996), does not hold that an employee may continue
to file charges on released claims based on conduct predating
the effective date of the release. Rather, that case stands for
the proposition that an employee who has released claims may not
be precluded from cooperating with an Equal Employment
Opportunity Commission investigation. Id. at 744-746.

14Dalrymple attempts to defeat summary judgment by claiming
that she thought the cases were related. The two sets of events
arose out of different facts and circumstances, as is evident
from the face of the MCAD charge and the grievances.
19

agreement. When considered in conjunction with her failure to

sign the release for eleven months, this conduct constituted a

material breach and repudiation of the agreement, which the town

was then no longer obligated to perform.15,16

2. Unjust enrichment. For the reasons well-stated by the

motion judge, equity does not compel the town to honor a

contract that Dalrymple had repudiated. "[I}n light of the

nature of the contract and the circumstances, it would be

inequitable to hold [the town] to an agreement . . . when it

could no longer receive a substantial portion of the benefit it

bargained for." Charles River Park, Inc., 28 Mass. App. Ct. at

816.

Conclusion. Because Dalrymple engaged in a material breach

of the contract, the town was relieved of its obligation to

perform. The town was entitled to summary judgment as a matter

of law.

Dalrymple's inclusion of other background facts predating
15

June 20, 2014, in the MCAD charge did not constitute a breach of
the agreement. The MCAD did not treat her recitation of the
history of litigation between the parties as a separate
violation, and it did not adjudicate any claims based on those
background facts. Cf. Cuddyer v. Stop & Shop Supermarket Co.,
434 Mass. 521, 530 n.10 (2001) (time barred events may still be
considered as background facts).

We do not decide whether the filing of the April 27 and
16

June 12, 2014 grievances (as opposed to the MCAD charge)
constituted a repudiation of the agreement, nor do we decide
whether the filing of grievances by the union fell within the
scope of the release.
20

Judgment affirmed.