A recreation of catch-me-if-you-can between Jed Walentas and Tom Brady’s former supervisor over a hurricane-damaged Bahamas mansion has come to an abrupt finish.
The Two Timber Administration CEO had been attempting to gather a $300,000 arbitration award from Will McDonough since final July, however repeatedly didn’t find him for formal authorized service, court docket filings present.
On Monday, Walentas notched a win when Manhattan Supreme Court docket Justice Kathleen Waterman-Marshall approved Walentas to serve McDonough through e mail and set October 27 because the date McDonough or his authorized group should present up at court docket to clarify why he shouldn’t be compelled to pay about $300,000 to Walentas.
Simply two days later, the sport was over. “The matter is resolved and the continuing is being discontinued,” Matthew Hearle, an lawyer for Walentas, confirmed to The Actual Deal. It isn’t but clear whether or not McDonough agreed to pay Walentas again.
McDonough didn’t return a request for remark.
Walentas and McDonough fashioned Bunkers Investments, LLC in 2015 to construct a luxurious rental property within the ultra-exclusive Bakers Bay resort within the Bahamas, in response to court docket paperwork.
To accumulate the property and construct the mansion, the companions contributed a mixed $4.9 million. Walentas supplied $2.45 million in money, whereas McDonough put in $750,000 in money together with $1.7 million in referral credit to offset the acquisition value. Any bills exceeding the preliminary capital, beneath their settlement, had been to be cut up equally.
The mansion was efficiently developed, however then got here a hurricane. Intensive harm required “a big infusion of recent capital to rebuild,” as insurance coverage payouts weren’t sufficient to cowl the repairs, court docket filings word.
Walentas paid “lots of of 1000’s of {dollars}” to maintain the property, whereas McDonough allegedly refused to pay his half, prompting the Two Timber CEO to begin arbitration in Might 2024.
A JAMS arbitration panel issued a $300,263 award in Walentas’s favor on July 16, 2025. One 12 months later, the developer has but to gather the money.
Walentas filed a proper petition in Manhattan Supreme Court docket to substantiate a JAMS arbitration award for the cash on July 9.
But it surely was the third time he had executed so — two earlier instances, filed in September and March had been each routinely dismissed as a result of Walentas’s authorized group didn’t find and serve McDonough.
Below New York legislation, winners of arbitration awards have precisely 12 months to ask a court docket to implement them, successfully making the third try the final probability for Walentas.
McDonough gained fame as Tom Brady’s de facto enterprise supervisor. Leveraging these connections into excessive finance, he became a Goldman Sachs vice chairman representing each Brady and Gisele Bündchen. He later pivoted to the tech sector, serving as CEO of the blockchain startup iCash. Since December 2025, in response to his LinkedIn web page, McDonough has served as a particular advisor on The White Home Process Power on the FIFA World Cup 2026.
On the helm of Two Timber Administration, the agency based by his father, Jed Walentas has redrawn Williamsburg’s skyline and repositioned the neighborhood. He turned the previous Domino sugar refinery on the Williamsburg waterfront right into a clubhouse for tech and AI firms. Two Timber executed greater than 380,000 sq. ft of business offers in 2025. Walentas additionally serves as chair of REBNY.
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