Former Tisbury Fire Chief Gregory Leland’s lawsuit against the town of Tisbury, alleging he was fired without constitutionally required notice, opportunity to be heard, or just cause, was dismissed Monday with prejudice by Judge Peter B. Krupp after Leland failed to appear at a status review hearing.
Neither Leland or his representation appeared at the Edgartown Courthouse Monday when the case was called at 2 pm. Lane Dubreuil, counsel for the town of Tisbury, noted that the matter was scheduled for 3 pm, and the court did a second call an hour later, but Leland remained absent.
“Do we have Mr. Leland?” Krupp asked the courtroom just after 3 pm.
Dubreuil told the court that he hasn’t received any contact from Leland or an attorney representing him.
“No sign of Mr. Leland here,” Krupp said. “It seems to me the case ought to be dismissed for failure to prosecute.”
The case was dismissed with prejudice, ending the suit and barring Leland from bringing the same claims against the town again.
The outcome on Monday followed a warning given by Krupp on July 15. Krupp wrote in court documents that failure of appearance from Leland or counsel may result in dismissal.
Leland also failed to appear at a July 7 hearing, when his attorneys Matthew David Provencher and Katherine McNamara Feodoroff were allowed by the court to withdraw from representing Leland. In an affidavit submitted by Provencher and Feodoroff, the two attorneys cited a breakdown in communication with Leland, “and therefore a concomitant breakdown in the attorney-client relationship.”
Leland sued the town of Tisbury and the select board in Dukes County Superior Court on April 24, 2025. He claimed the town ended his employment without notice and without just cause. The complaint sought $152,048.16, his annual salary, plus costs, interests, and attorney fees.
Leland was promoted to fire chief in 2020. In July 2024, Jay Grande, who was then town administrator, placed Leland on paid administrative leave, while the town investigated department management. An August 2024 report found that a romantic relationship between Leland and a subordinate damaged morale and recommended termination if the relationship continued. After an executive session on Oct. 24, 2024, his employment ended on Oct. 28.
After the decision, Dubreuil said he couldn’t comment further on the case. Tisbury town officials were not immediately available for comment.
The Times called Leland Construction, a company based in West Tisbury, and someone answered the phone but hung up after a reporter identified themselves. According to Leland’s LinkedIn profile, he is the owner and operator of Leland Construction.
