The lawsuit against the town of Tisbury from former Fire Chief Gregory Leland was dismissed with prejudice after he failed to appear at his last two hearings.

The lawsuit was filed on April 24, 2025 by Leland against the town for ending employment wihtout notice and without just cause. Leland claimed the municipality did not follow proper procedures when it fired him over accusations of favoritism and creating an uncomfortable work environment related to his relationship with the top paramedic supervisor, according to the Vineyard Gazette.

Leland was promoted to fire chief in 2020 and in 2024, Leland was placed on paid administrative leave while the town invesitagted department management. Town officials had questioned him about rumors of a relationship with a coworker for over a year, according to an internal inquiry by the town's attorney.

Although coworkers and employees in other municipal departments said it was well known that the two were dating, the town report said both parties denied a relationship.

One employee claimed to have heard concerns from fire department employees who believed the chief was ignoring the subordinate's tardiness and letting her choose her own schedule.

Leland claimed in his lawsuit that he and the paramedic supervisor had informed the town of the consensual connection. He said there was no proof the relationship violated town regulations.

After the investigation revealed that departmental morale had declined, the select board dismissed Leland in October 2025.

A communication breakdown between Leland and his lawyer earlier this year caused his case to fall apart. Katherine Feodoroff, his lawyer, asked Dukes County Superior Court Judge Peter Krupp in March whether she could drop the lawsuit, and in July she reported she still couldn't contact Leland.

“The situation here was for approximately six to eight months,” Feodoroff said at the time. “I was unable to contact him either by phone, via text, email or regular letter. There was zero contact.”

Judge Krupp declared the lawsuit would be dismissed with prejudice if Leland did not provide the court a reason to proceed by Oct. 5.

Leland and his representation did not appear at the hearing earlier this week, and even after rescheduling the hearing later that day, Leland was still absent. 

Leland cannot file a new lawsuit against the town on the same matter because the case was dismissed with prejudice.