Updated August 26.
Owners of the controversial Island Theatre have called on the courts to make a local resident compensate them with millions of dollars for allegedly backing out of a deal to buy the Oak Bluffs property.
Lucky 7 Realty Trust, represented by trustee Brian Hall, sued Jefrey DuBard, West Tisbury resident and founding partner of real estate development firm New Urban Collaborative, on July 29, alleging he breached contractual obligations in a deal for the down-Island theater, which town voters approved this past spring to be taken by eminent domain.
Benjamin Hall Jr., Brian Hall’s brother and property co-owner representing the case, declined to comment on a pending case.
DuBard pushed back on the case, saying while he spoke with the Halls about the possibility of purchasing the theater, “I strongly dispute the characterization of those discussions in the complaint.”
In an amended complaint, filed August 14 in the Dukes County Superior Court, which expands upon what was already submitted late last month and made only clerical corrections, the Halls allege that DuBard signed a $2.75 million offer for the Island Theatre in 2023 to “outbid” another offeror in bad faith. The complaint accuses DuBard of repeatedly making “differing excuses about the lack of payment of any deposit for some weeks” before ultimately indicating he would not be able to pay.
The Halls asked the court to order DuBard pay a total of $8.25 million, triple the alleged offer, on top of interest and attorney’s fees incurred by the trust.
The suit alleges that DuBard intentionally misrepresented his intentions when entering into an agreement for the theater. It also alleges DuBard has been involved in “similar disputes involving his misrepresentation and breaches of contracts” in Massachusetts.
DuBard’s alleged behavior “thwarted [Lucky 7 Realty] Trust’s efforts to then sell the theater” because the other buyer “moved on to other matters” and lost interest in discussions or negotiations, the complaint reads.
Island Theatre is a dilapidated property that has sat empty on Circuit Avenue in Oak Bluffs since 2012. The Halls previously stated a desire to sell to a private buyer, and said a lack of wastewater availability from the town deterred interested investors.
But public dissatisfaction with the building led Oak Bluffs residents to approve, in a landslide vote this April, to allow the town to initiate an eminent domain seizure of the property, which opened up to $5 million for various costs, including initial improvements, legal fees, planning, and demolition; the actual development of the property was not included in that approved number. Buying the theater outright was also placed as an option during the town election, and the Halls have stated the asking price was $2.8 million. The town is considering next steps through a working group.
DuBard said there is no record to support the Halls’ allegations that he led to the prevention of the property being sold.
“I also categorically deny any allegation that I acted fraudulently or intentionally interfered with another prospective purchaser,” DuBard said. “I wish the Halls well, and most importantly, I hope the Island Theatre ultimately has a positive future for Oak Bluffs and the Island.”
The Halls filed a demand for a jury trial for the amended complaint, on August 17, but the case may take some time for a resolution. According to the MassCourts database, judgment isn’t due until at least July 31, 2028.
Editor’s Note: Updated with comments from Jefrey DuBard.

