ROBERT DOYLE v. PETER LYDON (2026)

MEMORANDUM AND ORDER PURSUANT TO RULE 23.0

These consolidated and companion cases arose after two long-time business partners, Robert Doyle (plaintiff) and Peter Lydon (defendant), developed bad blood over the course of a real estate transaction. We affirm the Superior Court judgment on the merits ordering specific performance, the order of a single justice of this court denying the defendant's motion to stay the judgment on the merits, the Superior Court findings and order of sanctions on the plaintiff's complaint for contempt of the judgment on the merits, and the denial of the defendant's motion for clarification of the sanctions order.

Background. “We summarize the undisputed facts drawn from the summary judgment record,” reserving some facts for our discussion below; “to the extent the record includes disputed evidence, we consider that evidence in the light most favorable to [the nonmoving party].” Cesso v. Todd, 92 Mass. App. Ct. 131, 132 (2017), citing Ritter v. Massachusetts Cas. Ins. Co., 439 Mass. 214, 215 (2003).

In 2019, the plaintiff and the defendant co-owned two nearly adjacent properties in South Boston as tenants in common. The parties negotiated to exchange their ownership shares through a real estate transaction so that each would own one of the properties outright. In July 2019, they entered into a written co-ownership agreement (co-ownership agreement) and, in the fall of 2020, executed purchase and sale agreements for each property (purchase and sale agreements).

Pursuant to the co-ownership agreement, the parties intended for their ownership swap to qualify for favorable tax treatment under Section 1031 of the Internal Revenue Code (§ 1031). The parties understood, and the co-ownership agreement stated, that to qualify for § 1031 treatment they would have to hold both properties as tenants in common for at least one year before exchanging their ownership interests. The parties agreed to execute the transaction within thirty days after the end of that holding period.

Two days after they signed the purchase and sale agreements, the defendant informed the plaintiff and the bank that held the mortgages on the properties that he no longer intended to go through with the deal. The plaintiff filed suit, alleging breach of contract and seeking specific performance (the merits case). A judge of the Superior Court (merits judge) allowed summary judgment for the plaintiff on his breach of contract claim and concluded that the plaintiff was entitled to specific performance. On May 7, 2024, final judgment entered ordering the defendant, in relevant part, “to fully perform and close the transaction required in the parties’ [agreements], and to do so by July 5, 2024” (final judgment). On June 27, 2024, the defendant filed an emergency motion to stay enforcement of the final judgment, which was denied by another judge of the Superior Court (contempt judge). He then filed a motion to stay the final judgment with this court, which was denied by a single justice. The defendant appealed both from the final judgment and the single justice order denying his motion to stay. These appeals were consolidated.

The closing did not occur by the deadline set by the final judgment, so the plaintiff filed a complaint for contempt (the contempt case). After an evidentiary hearing, the contempt judge concluded that the defendant was in contempt and ordered sanctions to compel his compliance with the final judgment. The defendant's appeal from the contempt findings, the order of sanctions, and the denial of the defendant's subsequent motion for clarification of the sanctions order, was paired for consideration with his other appeals.

Discussion. We begin with the merits case. We conclude that (1) summary judgment was appropriately entered for the plaintiff and (2) the single justice did not err in denying the defendant's motion for a stay pending appeal. We then address the contempt case and affirm the contempt judge's findings and sanctions order.

1. The merits case. a. Summary judgment. 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” (citation omitted). Casseus v. Eastern Bus Co., 478 Mass. 786, 792 (2018). “The moving party bears the burden of affirmatively demonstrating the absence of a triable issue.” 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 genuine issue of material fact.” French King Realty Inc. v. Interstate Fire & Cas. Co., 79 Mass. App. Ct. 653, 659-660 (2011).

i. Breach of contract and specific performance. “A seller's repudiation of [his] contractual obligation makes unnecessary any tender of performance or offer of performance by the buyer, and where it is established that the buyer was ready, willing, and able to perform, specific performance is the appropriate remedy.” Coviello v. Richardson, 76 Mass. App. Ct. 603, 610 (2010). “[R]epudiation of a contract is a material breach.” Id. at 609. As the buyer, the plaintiff bore the burden of establishing his ability to perform. See Kanavos v. Hancock Bank & Trust, 395 Mass. 199, 204 (1985).

Here, viewed in the light most favorable to the defendant, the undisputed facts reflect repudiation by the defendant. One week before the closing deadline, the defendant told the plaintiff and the bank that held the mortgages on the properties that he “[did] not intend to move forward” and instructed the bank to “take no further action in furtherance of this [transaction].” From then until the closing date, the defendant refused to exchange property interests as required by the agreements. Thus, the defendant “clearly manifested a refusal to perform” under the agreements. Coviello, 76 Mass. App. Ct. at 610.

The plaintiff, meanwhile, had sufficient funds to close the transaction, and behaved consistently with an intent to close: he continued discussions with the bank to close as scheduled and reiterated to the defendant that he was prepared to close. “This constitutes ample evidence that the [plaintiff was] ready, willing, and able to perform ․” Pierce v. Clark, 66 Mass. App. Ct. 912, 913 (2006). Accordingly, the merits judge properly allowed summary judgment for the plaintiff on the breach of contract claim and specific performance was appropriate. See Coviello, 76 Mass. App. Ct. at 610.

It is not meaningful that the defendant communicated, after the contractual closing date, that he was open to renegotiating. The agreement includes a “time is of the essence” clause, and “[w]hen parties agree in writing that time is to be of the essence, courts will hold parties to the deadlines they have imposed upon themselves” (citation omitted). Perroncello v. Donahue, 64 Mass. App. Ct. 564, 568 (2005), S.C., 448 Mass. 199 (2007) (reversed on other grounds). As to the plaintiff's purported inability to perform, the defendant cannot avoid his contractual obligations by relying on the bank's failure to complete loan modification documents when the defendant caused the bank to stop work on them. See Lobosco v. Donovan, 30 Mass. App. Ct. 53, 56 (1991).

The defendant also asserts that, even if he did repudiate the contract, his repudiation is excused because (1) the plaintiff committed misconduct in managing one of the properties during the holding period, in violation of the co-ownership agreement; and (2) the defendant was advised that the transaction would not qualify for favorable treatment under § 1031. Again, we are unpersuaded.

The co-ownership agreement is not ambiguous, so its interpretation is a question of law. See Eigerman v. Putnam Invs., Inc., 450 Mass. 281, 287 (2007). We do not look beyond the four corners of a contract where unambiguous language does not “support [a] reasonable difference of opinion as to the meaning of the words employed and the obligations undertaken” (citation omitted). Indus Partners, LLC v. Intelligroup, Inc., 77 Mass. App. Ct. 793, 796 (2010).

As to the first argument, we conclude that the co-ownership agreement governs the ownership of the properties; it does not impose operational or management restrictions. The plaintiff's second argument is similarly unsupported by the co-ownership agreement because that agreement does not condition the exchange on successful tax treatment under § 1031. Instead, the co-ownership agreement addresses § 1031 only by requiring that the swap take place no sooner than one year after the parties took ownership of the properties as tenants in common. The parties bore the risk that the transaction would not qualify for § 1031 treatment. Cf. John J. Duane Realty Corp. v. Great Atl. & Pac. Tea Co., 8 Mass. App. Ct. 899, 900 (1979). The parties are bound by the terms of their unambiguous contract; the dismissal of the defendant's breach of contract defense and counterclaim on those grounds was appropriate. See Eigerman, 450 Mass. at 287; Indus Partners, LLC, 77 Mass. App. Ct. at 796.

ii. Unclean hands. Courts apply the unclean hands doctrine to deny equitable relief that is otherwise appropriate “to prevent a party from benefiting by his dishonesty.” Fisher v. Fisher, 349 Mass. 675, 677 (1965). A party may be denied equitable relief under the doctrine only where his conduct is “tainted with the inequitableness or bad faith relative to the matter in which [he] seeks relief” (citation omitted). Murphy v. Wachovia Bank of Del., N.A., 88 Mass. App. Ct. 9, 15 (2015). The challenged inequitable conduct “must directly affect the claim being brought.” Amerada Hess Corp. v. Garabedian, 416 Mass. 149, 156 (1993).

Whether to apply the doctrine is “committed to the broad discretion of the trial judge.” Fales v. Glass, 9 Mass. App. Ct. 570, 575 (1980). We will reverse only where the judge makes a “clear error of judgment in weighing the factors relevant to the decision ․ such that the decision falls outside the range of reasonable alternatives.” Spinosa v. Tufts, 98 Mass. App. Ct. 1, 6 (2020), quoting L.L. v. Commonwealth, 470 Mass. 169, 185 n.27 (2014). “In our review of a motion for summary judgment we are confined to an examination of the materials before the court at the time the rulings were made” (quotation and citation omitted). Herbert A. Sullivan, Inc. v. Utica Mut. Ins. Co., 439 Mass. 387, 400 (2003).

The defendant maintains that the plaintiff's alleged mismanagement of one of the properties between 2012 and 2013 barred specific performance as a remedy. The parties negotiated the contract under which the plaintiff sought specific performance in 2019. The alleged mismanagement of which the defendant complains predated that contract by six or seven years. The merits judge concluded that the gap in time rendered the connection too attenuated to justify the application of the unclean hands doctrine. Instead, he allowed the defendant to pursue at trial a counterclaim alleging that the conduct cited in support of his unclean hands argument constituted a breach of fiduciary duty by the plaintiff. We discern no abuse of the merits judge's broad discretion. See Amerada Hess Corp., 416 Mass. at 156; Fales, 9 Mass. App. Ct. at 575.

b. Denial of the motion for a stay pending appeal. To obtain a stay, a party must prove four things: (1) a likelihood of success on the merits, (2) irreparable harm absent a stay, (3) lack of substantial harm to other parties if a stay were granted, and (4) in cases implicating the public interest, that there would be no harm to the public from a stay. See C.E. v. J.E., 472 Mass. 1016, 1017 (2015). We review the single justice's denial of the defendant's motion for an abuse of discretion, which occurs only where “the decision falls outside the range of reasonable alternatives.” L.L., 470 Mass. at 185 n.27.

That is not the case here. In arguing his likelihood of success on the merits, the defendant raised the same issues we considered in his challenge to the summary judgment ruling. For the reasons explained in our discussion of the merits, we are not persuaded the single justice abused her discretion in denying the stay motion and thus discern no error of law or abuse of discretion. See C.E., 472 Mass. at 1017. See also Mezoff v. Cudnohufsky, 5 Mass. App. Ct. 874, 874 (1977) (“Rarely, if ever, can it be said that a single justice is in error in denying relief”).

2. The contempt case. The defendant raises three challenges to the contempt judgment. First, he contends that the final judgment was not “unequivocal.” Second, he maintains that he was barred from presenting his impossibility defense during the evidentiary hearing on the contempt complaint. Finally, he asserts that the contempt judge abused her discretion by failing to consider a reasonable alternative to coercive sanctions.

A finding of civil contempt requires “clear and convincing evidence of disobedience of a clear and unequivocal command.” Birchall, petitioner, 454 Mass. 837, 853 (2009). An “unequivocal command” is one that provides “adequate notice of the required ․ activity” (citations omitted). Lynch v. Police Comm'r of Boston, 51 Mass. App. Ct. 772, 776 (2001). The defendant must also “have the ability to comply with the order.” Cooper v. Keto, 83 Mass. App. Ct. 798, 804 (2013). “We review the judge's ultimate finding of contempt for abuse of discretion, but we review underlying conclusions of law de novo and underlying findings of fact for clear error.” Commercial Wharf E. Condominium Ass'n v. Boston Boat Basin, LLC, 93 Mass. App. Ct. 523, 532 (2018).

The final judgment required the defendant to “fully perform and close the transaction required in the parties’ Real Estate Co-Ownership Agreement dated July 24, 2019, and their Purchase and Sale Agreements, and to do so by July 5, 2024.” That the defendant would have been required to cooperate with the plaintiff to complete the transaction does not render the terms “subject to discretionary judgment.” Lynch, 51 Mass. App. Ct. at 777. Cf. Cooper, 83 Mass. App. Ct. at 807-808. The parties’ contract reflected agreement on the steps required for performance. That is sufficient. See Lynch, supra (contemnor must be given “clear and unequivocal notice concerning the specific steps he was required to take to [comply]”). See also Cooper, supra. We discern no abuse of discretion.

We are also unpersuaded that the contempt judge erred with respect to the defendant's impossibility defense. “Noncompliance with a court order may be excused where compliance becomes impossible, but the burden of proving impossibility lies with the alleged contemnor.” Commonwealth v. One 1987 Ford Econoline Van, 413 Mass. 407, 412 (1992). “[T]his burden is a difficult one to meet.” Id. “The defense of impossibility is unavailing where an alleged contemnor is responsible for [their] inability to comply.” Allen v. School Comm. of Boston, 400 Mass. 193, 195 (1987).

The defendant contends that he was excused from complying with the final judgment because it was not possible to complete a successful § 1031 exchange. He proffered that his proposed expert witness would so testify. But, as discussed above, no term of the parties’ contract required a successful § 1031 exchange. Accordingly, the expert's testimony had no bearing on whether the defendant attempted to comply with the final judgment, so it was not an abuse of discretion for the contempt judge to preclude the expert from testifying. And because “the [defendant] did not present evidence that [he] was reasonably diligent and energetic in attempting to accomplish what was ordered, the judge was warranted in concluding that the [defendant] did not meet [his] burden of proving that compliance was impossible.” (quotation and citation omitted). One 1987 Ford Econoline Van, 413 Mass. at 412. For this reason, we also find no error in the contempt judge's denial of the defendant's motion for clarification of the sanctions order, which raised similar arguments.

We are also satisfied that the contempt judge did not err with respect to the remedy imposed. “[T]he purpose of civil contempt is remedial: its aim is to coerce the performance of a required act by the disobedient party for the benefit of the aggrieved complainant.” Sodones v. Sodones, 366 Mass. 121, 129-130 (1974). The “formulation of [remedies] is within the judge's discretion.” Eldim, Inc. v. Mullen, 47 Mass. App. Ct. 125, 129 (1999). The defendant had not taken any steps to comply with the final judgment in the six months between its entry and the evidentiary hearing on the contempt complaint. On this record, it was not an abuse of discretion for the contempt judge to impose sanctions to compel compliance. See Birchall, petitioner, 454 Mass. at 850-851.³

For these reasons, the judgment entered May 7, 2024, is affirmed, the order of the single justice entered August 7, 2024, is affirmed, the findings for contempt and sanctions order entered October 22, 2024, is affirmed, and the order denying the motion for clarification of the October 22 sanctions order entered October 22, 2024, is affirmed.

So ordered.

FOOTNOTES

3.   The plaintiff's requests for appellate attorney's fees are denied.