A legal battle between the owner of a multi-story apartment building in Oak Bluffs and the Martha’s Vineyard Commission is set to go to trial later this month.

Windsor Circuit Ltd., the owner of the building that formerly housed the Lampost, is seeking to overturn a 2022 commission decision that denied the company’s request to reduce the number of restricted workforce housing units in what used to be the bar’s upper three floors. 

The lawsuit, filed two years ago, is scheduled to have a bench trial on Oct. 28, one of several recent legal challenges to test the mettle of the commission’s decisions. 

Attorneys for both the commission and Windsor Circuit gave a preview into the trial’s arguments at a hearing Monday before Dukes County Superior Court Judge James Lang. 

Windsor Circuit gained permission from the commission in 2018 to convert the upper levels of the lower Circuit avenue building into 10 apartments. The commission said it approved the project with the understanding that all of the apartments would be used for workforce housing. 

But in 2021, it came to light that the Windsor Circuit, led by Adam Cummings, had been renting out units on AirBNB as short-term rentals. 

Mr. Cummings later asked the commission to ease up on the restrictions, dropping the number of units that had to be solely for workforce housing to four. 

The commission denied the request in 2022, prompting the lawsuit later that year. 

Windsor Circuit attorney Thomas Orr told Judge Lang on Monday that his client was contesting that the commission denial of the modification was legally tenable, arguing that there was ambiguous language in the previous approval.

The commission’s written approval of the 10 apartments said the units “shall be rented to employees of local businesses either as permanent year-round housing or temporary housing as needed.”

The “as needed” phrase is at the heart of the dispute, with the commission arguing that it was referring to whether the housing was to be used for year-round or seasonal purposes. Though the commission has said that it intended for all 10 units to be used for workforce housing, Mr. Orr said the language doesn’t implicitly state that. 

“There’s a need for workforce housing on the Island,” Mr. Orr said. “We don’t dispute that. What we do dispute is the scope of the workforce housing restriction on this project.” 

At Monday’s hearing, the last planned ahead of trial, Mr. Orr also argued that procedural issues with the commission’s decision tainted the process and “poisoned the well.”

Judge Lang probed Mr. Orr’s arguments at the 75-minute hearing, as well as those of commission attorney Johanna Schneider. 

Ms. Schneider argued that the commission intended for all 10 units to be used for workforce housing. 

“The commission imposed fair conditions in order to mitigate the potential detriments from this project,” Ms Schneider said. “What the applicant believed, or what the applicant wanted, or whether he wanted flexibility or didn’t agree to a certain condition, are utterly irrelevant in this situation.” 

The judge wasn’t convinced that the language in the commission’s approval left no room for other interpretations. 

“The phraseology itself, of the condition, it seems to me is not crystal clear,” Judge Lang said. “It seems to me that reasonable arguments can be made as to what “as need” was modifying.” 

He was interested in looking at some of the intent behind the decision to come to a better conclusion. 

Judge Lang also set out some perimeters for who could testify during the trial. Past efforts by Windsor Circuit to call commissioners to the stand are unlikely to go forward, as the judge indicated he believed they were exempt under the deliberative privilege. Meeting recordings, minutes and other documents would be allowable during trial.

The judge did seem amenable to having expert witnesses testify to the workforce housing shortage on the Island and how that could factor into the commission’s decision. 

The commission, which reviews large-scale projects and other developments that are expected to have a regional impact, has been sued several times in recent years over its decisions. The commission came to a settlement with Oak Bluffs homeowners over a request to demolish a historic home; won a case in which a developer tried to overturn a denial of a subdivision on Meeting House Way, and lost a case over the commission’s stringent rules on an elderly affordable housing expansion in Oak Bluffs. 

There is a chance the Windsor Circuit case could be delayed, Judge Lang warned Monday, if a personal injury lawsuit before the Dukes County Superior Court goes to trial on Oct. 28.