Former Tisbury Fire Chief Gregory Leland’s lawsuit against the town of Tisbury is at risk of dismissal after his former attorneys withdrew their representation, and he failed to appear at a hearing in July.
A status review hearing is scheduled for Monday, Oct. 5 at 3 pm at the Edgartown Courthouse. If Leland doesn’t appear in person or through an attorney, the case could be dismissed, according to court documents.
“Failure of Mr. Leland to appear individually, or through counsel who file an appearance for all purposes, may result in the dismissal of the case with prejudice,” Judge Peter B. Krupp wrote on July 15 in court documents.
A dismissal with prejudice would end the suit and bar Leland from bringing the same claims against the town a second time.
Leland sued the town of Tisbury and the select board in Dukes County Superior Court on April 24, 2025. He claimed that the town ended his employment without constitutionally required notices, opportunity to be heard, and without just cause, violating his employment agreement with the town. The complaint said Leland suffered losses in the amount of $152,048.16, his annual salary. He also hoped to receive payment for costs, interest, and his attorneys fees for what the complaint claims was a willful breach of contract.
Leland was promoted to fire chief in Tisbury in 2020 after two years as assistant chief. In July 2024, however, former town administrator Jay Grande placed him on paid administrative leave, while the town, through a Boston-based KP Law investigation, reviewed department management and operations.
A report completed in August 2024, later obtained by The Times, found that a romantic relationship between Leland and a subordinate created an uncomfortable workplace and damaged morale. Employees described favoritism in scheduling and duties, poor communication, and concerns about the chief’s availability. The report recommended termination if the relationship continued. Leland later said he disclosed the relationship to town officials in late February or early March 2024 and denied favoritism.
After an executive session on Oct. 24, 2024, Grande said Leland’s employment would end Oct. 28. In a statement the next day, Leland said the select board terminated him without cause and in violation of his contract and that he intended to sue.
Leland didn’t appear at a hearing at the Edgartown Courthouse on July 7, where his attorneys, Matthew David Provencher and Katherine McNamara Feodoroff, made a motion to withdraw from representing him. Their motion was allowed on July 15.
In a withdrawal affidavit, Leland’s attorneys wrote that there had been a breakdown in communications with their client, “and therefore a concomitant breakdown in the attorney-client- relationship.”
The attorneys also said there were no motions or discovery requests currently pending in the case, and no trial date had been set.
“We filed a motion to withdraw — which was allowed by the court,” Provencher said in an interview with The Times on Thursday, Oct. 1. Attorney Lane Dubreuil, who represented the town of Tisbury in this case, declined to comment.
As of Friday afternoon, no new attorney is listed for Leland in court documents.
