BankUnited revives loan dispute with Harry Macklowe
BankUnited is not walking away from a $14.2 million loan dispute with Harry Macklowe just yet. After losing the trial in April, the lender is now taking the legendary Manhattan developer to an appeals court.
The dispute stems from a development loan the lender issued to Macklowe in December 2013. Macklowe used rent revenue from a Walgreens lease at 310 East 53 Street — for which, according to the lawsuit, he signed for 99-years in 2006 — to service the loan. But in March 2022, two months after the lease expired without the tenant extending the option, Macklowe defaulted on the note.
Between December 2013 and October 2022, Macklowe had paid off just over a quarter of the original loan, according to court documents, leaving a $10.5 million principal balance. BankUnited filed a lawsuit in November 2022 against his entity, Gray-Line Development, and Macklowe for nearly $12 million in unpaid principal, interest and fees.
BankUnited secured an early partial win in November 2024, when a judge ordered Macklowe to pay missing monthly payments of $67,000 until he secured a new tenant for the commercial space. The space has remained vacant ever since.
That wasn’t enough for BankUnited. In September 2025, the plaintiff pushed the case to a bench trial, claiming that if the property can’t make money to repay the loan, Macklowe had to personally pay down the remaining millions.
This April, the bank’s legal pursuit collapsed when Judge Jennifer G. Schecter ruled in Macklowe’s favor, explicitly stating in the decision that the agreement did not establish basic terms.
The document “does not clearly set forth the most basic, fundamental terms of the guaranty: how much Macklowe must pay and when he must pay,” the ruling says.
Additionally, the court found no proof of the parties’ “meeting of the minds,” or mutual agreement on the terms of the agreement, pointing out that internal notes presented by BankUnited as a proof were never actually shared with Macklowe or his team during negotiations.
The ruling revealed that BankUnited had tried to get Macklowe to retroactively agree to their interpretation after realizing the documents were missing material terms. Macklowe refused, which could be construed, the judge Schecter wrote, as “further evidence of a lack of a meeting of the minds or simply as Macklowe being opportunistic.”
Ultimately, “incoherent” BankUnited’s paperwork had resulted in the trial victory for Macklowe.
The bank, however, is not backing down just yet. The appeal filed on May 28 was formalized with the Appellate Division, First Department in New York on June 24, setting the stage for the next chapter of the legal battle.
Attorneys for both BankUnited and Macklowe did not immediately return requests for comment.
Macklowe is navigating other major court cases. In June, an appellate court handed the developer a setback in his ongoing litigation over alleged construction defects at his ultra-luxury supertall, 432 Park Avenue.
The court rejected Macklowe’s bid to force the building’s condo board to cover his mounting legal fees in a 2021 lawsuit that claims the developer left the tower “riddled” with construction defects, including “intolerable” noise issues, flooding and cracks in the walls.
Read more
Housing Notes: Developers are in on the joke: Apologize later
New York judges deal setback for Harry Macklowe in 432 Park legal battle
Harry Macklowe tries selling 432 Park home he lost
