Jed Walentas, former Tom Brady manager settle over Bahamas mansion

A game of catch-me-if-you-can between Jed Walentas and Tom Brady’s former manager over a hurricane-damaged Bahamas mansion has come to an abrupt end.

The Two Trees Management CEO had been trying to collect a $300,000 arbitration award from Will McDonough since last July, but repeatedly failed to locate him for formal legal service, court filings show.

On Monday, Walentas notched a win when Manhattan Supreme Court Justice Kathleen Waterman-Marshall authorized Walentas to serve McDonough via email and set October 27 as the date McDonough or his legal team must show up at court to explain why he shouldn’t be forced to pay about $300,000 to Walentas.

Just two days later, the game was over. “The matter is resolved and the proceeding is being discontinued,” Matthew Hearle, an attorney for Walentas, confirmed to The Real Deal. It is not yet clear whether McDonough agreed to pay Walentas back.

McDonough did not return a request for comment.

Walentas and McDonough formed Bunkers Investments, LLC in 2015 to build a luxury rental property in the ultra-exclusive Bakers Bay resort in the Bahamas, according to court documents.

To acquire the property and build the mansion, the partners contributed a combined $4.9 million. Walentas provided $2.45 million in cash, while McDonough put in $750,000 in cash along with $1.7 million in referral credits to offset the purchase price. Any expenses exceeding the initial capital, under their agreement, were to be split equally.

The mansion was successfully developed, but then came a hurricane. Extensive damage required “a large infusion of new capital to rebuild,” as insurance payouts were not enough to cover the repairs, court filings note.

Walentas paid “hundreds of thousands of dollars” to sustain the property, while McDonough allegedly refused to pay his half, prompting the Two Trees CEO to commence arbitration in May 2024.

A JAMS arbitration panel issued a $300,263 award in Walentas’s favor on July 16, 2025. One year later, the developer has yet to collect the cash.

Walentas filed a formal petition in Manhattan Supreme Court to confirm a JAMS arbitration award for the money on July 9.

But it was the third time he had done so — two previous cases, filed in September and March were both automatically dismissed because Walentas’s legal team failed to locate and serve McDonough.

Under New York law, winners of arbitration awards have exactly 365 days to ask a court to enforce them, effectively making the third attempt the last chance for Walentas.

McDonough gained fame as Tom Brady’s de facto business manager. Leveraging those connections into high finance, he became a Goldman Sachs vice president representing both Brady and Gisele Bündchen. He later pivoted to the tech sector, serving as CEO of the blockchain startup iCash. Since December 2025, according to his LinkedIn page, McDonough has served as a special advisor on The White House Task Force on the FIFA World Cup 2026.

At the helm of Two Trees Management, the firm founded by his father, Jed Walentas has redrawn Williamsburg’s skyline and repositioned the neighborhood. He turned the former Domino sugar refinery on the Williamsburg waterfront into a clubhouse for tech and AI companies. Two Trees executed more than 380,000 square feet of commercial deals in 2025. Walentas also serves as chair of REBNY.