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Former Massachusetts planning official sues, alleging retaliation over permit objections

She was placed on administrative leave during an investigation into her conduct.

A woman discusses printed plans on a table in an office setting with a computer and a printer in the background.

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A former Massachusetts town official filed a lawsuit that claims other town officials pushed her out after she raised concerns about how a controversial development was permitted.

Former planning board administrator Amy Upton filed a lawsuit in July against several officials in her town of Tisbury, Massachusetts, according to the Vineyard Gazette

Here's what to know

According to the Gazette, Upton claims that she pushed against the town's permitting process starting in 2024, when she alleges that residents complained about work being performed on property owned by the real estate developer, Xerxes Aghassipour. 

Upton claimed that Aghassipour should have applied for a special permit for his project, which was a nine-bedroom home. 

The complaint also says, as the Gazette reported, that former town administrator Jay Grande urged Upton not to pursue the matter, saying that "time is of the essence" for completing the projects.

More background

According to the Gazette, the planning board directed Upton in June 2024 to ask building inspector Greg Monka to send one of Aghassipour's projects back to the board for review.

Upton contends that Monka ignored those repeated requests. 

Upton also alleges that Monka prevented her from speaking with building department staff without his approval and altered forms to bypass the planning board and speed up approvals.

The Gazette reported that Aghassipour later sought records that made Upton's private texts about that meeting public. She was then placed on administrative leave during an investigation into her conduct, and the same episode led to a separate lawsuit against both Upton and the town that was eventually dismissed.

By December 2024, Upton had asked human resources for an outside investigation, the Gazette reported, saying a hostile work environment was affecting her health. In October 2025, Upton was reassigned to report directly to Monka, the same official she had accused of misconduct.

The Gazette reported that town counsel later found Upton had been insubordinate, had often logged overtime without approval, and had treated disagreement as harassment.

What's being done?

The Gazette reported that the town has not yet answered the lawsuit in court and that no initial hearing has been scheduled. Town officials are also still trying to determine who the planning board administrator should report to, leaving that governance question unresolved.

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