A long-simmering legal dustup between Two Trees CEO Jed Walentas and Will McDonough, a longtime business manager who once handled Tom Brady’s affairs, has ended with surprisingly little drama. Court papers filed this week say the case has been discontinued, wrapping up a fight over a hurricane-damaged Bahamas property and a roughly $300,000 arbitration award before it ever reached a public hearing.
Walentas had been trying to collect a JAMS award of $300,263 and last week filed a petition in Manhattan Supreme Court to confirm the decision. Justice Kathleen Waterman-Marshall authorized service by email and set October 27 as the date McDonough or his counsel would have to appear and show cause. Earlier efforts by the developer to enforce the award were twice dismissed after his lawyers failed to locate and serve McDonough, according to The Real Deal.
Walentas and McDonough formed Bunkers Investments LLC in 2015 to build a luxury rental at Baker’s Bay, and court filings reviewed by reporters show the partners put in a combined $4.9 million: $2.45 million from Walentas and roughly $750,000 in cash plus $1.7 million in referral credits from McDonough. After a hurricane damaged the mansion, insurance proceeds did not cover all the repairs and Walentas alleges he picked up “hundreds of thousands” of dollars in costs. That dispute led to arbitration in May 2024, and a JAMS panel issued the award on July 16, 2025. Two days after the judge approved email service, Matthew Hearle, an attorney for Walentas, told The Real Deal, “The matter is resolved and the proceeding is being discontinued.”
The legal clock that pushed the filing
Arbitration winners have to move fast. Under the Federal Arbitration Act, a party generally has one year to ask a court to confirm an award, which helps explain why Walentas kept coming back to court even after earlier petitions were dismissed. See the Federal Arbitration Act (9 U.S.C. § 9) for the statutory deadline in the U.S. Code.
Local implications for Two Trees
By big-developer standards, the money at stake was relatively modest. The dispute still drew attention because it involved a prominent New York landlord. Jed Walentas runs Two Trees, the Brooklyn firm behind Domino Park and the Refinery at Domino, whose recent deals have kept the company in the local headlines. That visibility helped turn what might have been a quiet contract spat into a city story, as reported by Commercial Observer and on Two Trees' Domino Park site.
What we still don't know
Neither side disclosed settlement terms in public filings, and McDonough did not return a request for comment filed with reporters. With the proceeding discontinued, the court docket no longer lists a show-cause hearing, and there is no public record yet of payment or any further action.
