Former Tisbury fire chief Gregory Leland’s lawsuit against the town was dismissed in court this week after he failed to show up to the last two hearings.
Mr. Leland sued Tisbury last year and claimed the town did not follow proper procedures when he was terminated over allegations of favoritism and creating an uncomfortable work environment connected to his relationship with the leading paramedic supervisor.
But his case started to crumble earlier this year when there was a breakdown in communication between Mr. Leland and his attorney. In March, Mr. Leland’s attorney Katherine Feodoroff asked Dukes County Superior Court Judge Peter Krupp if she could withdraw from the case, and in July said she still hadn’t been able to talk to Mr. Leland.
“The situation here was for approximately six to eight months,” Ms. Feodoroff said at the time. “I was unable to contact him either by phone, via text, email or regular letter. There was zero contact.”
At that point, Judge Krupp ruled that if Mr. Leland did not give a court a reason to continue the case by Oct. 5, it would be tossed out with prejudice.
When the case was called again on Monday, Mr. Leland was not in attendance, and the judge ordered it be dismissed. Because the case was dismissed with prejudice, Mr. Leland cannot bring another lawsuit against the town on the same issue.
After the brief hearing Tuesday, Tisbury’s attorney Lane Dubreuil declined to comment on the win. Mr. Leland did not respond to a request for comment.
Tisbury put Mr. Leland on administrative leave in the summer of 2024. An internal investigation conducted by the town’s attorney found that town officials had been asking Mr. Leland about rumors of a relationship with a coworker that had been going on for more than a year.
The town report claimed that both parties denied a relationship, but coworkers and staff in other town departments said it was widely known that the two were dating.
One employee said they had heard complaints from fire department staff who felt the chief was allowing the subordinate to make her own schedule and overlooked her coming in late.
In his lawsuit, Mr. Leland argued he and the paramedic supervisor had notified the town of the consensual relationship. He contended there was no indication that the relationship violated town policies.
The select board fired Mr. Leland in October 2025 after the investigation found that morale in the department had sunk.
Mr. Leland was the chief in Tisbury from 2020 until 2024.
This article appears in October 9 2026.