Photo: Brandon Bell/Getty Images

On Tuesday, a federal judge ordered Rudy Giuliani to hand over nearly all of his worldly possessions as damages in the $148 million defamation lawsuit he lost in late 2023. Everything on the list must go to a court-appointed bankruptcy trustee within seven days. then finally to Ruby Freeman and Shaye Moss, a mother-daughter group of Georgia poll workers who falsely accused Giuliani of manipulating ballots in the 2020 presidential campaign. The items Freeman and Moss now own include a Mercedes-Benz, a signed Joe DiMaggio shirt, a television, furniture, several luxury watches – and a penthouse apartment on the Upper East Side.

Giuliani first put the three-bedroom, three-bathroom penthouse at 45 East 66th Street up for sale in 2023, listing it with Serena Boardman at Sotheby’s (she was also responsible for the sale of Bernie Madoff’s penthouse). That was before Giuliani lost the defamation lawsuit, but he was still in the middle of several other legal battles stemming from his escapades in and around the Trump administration and was “virtually broke,” according to his lawyer. (In 2021, the apartment was raided by the FBI as the agency investigated Giuliani’s dealings with Ukraine.) The former mayor took it off the market in February 2023 when it failed to sell at an original price of $6.5 million could, but put it back on the market In May this year, his lucrative radio show was canceled – after he fell out with the station’s owner, John Catsimatidis.

Now Giuliani won’t see any of the money. But owning a co-op on the Upper East Side isn’t necessarily an easy payday, even if Freeman and Moss just want to sell it and take the money.

Photo: Sothebys International Realty

Photo: Sothebys International Realty

“In the short term, I think it will definitely make their lives more difficult,” said Jed Garfield, an Upper East Side real estate agent. The co-op charges $10,000 in monthly maintenance fees. However, it is unclear whether election officials will cover this amount or whether the bankruptcy trustee may have to sell other assets to pay it. Aside from that, Giuliani had to reduce the price of the apartment by $400,000, even though the co-op market is currently strong. It is now for sale for $5.1 million.

It’s also simply Rudy Giuliani’s former apartment. He bought the property in the prime of his career, as his second term as mayor ended. Judith Giuliani, his ex-wife, told the New York Just It was a gilded retreat where her then-husband, still in his bright “Mayor of America” era, “could smoke cigars and relax and watch his Yankee games.” It was supposedly very It was important to him that he lived in a penthouse. (In fact, he fought to prevent another penthouse from being built above his.)

Having his name attached to the building was once an asset, said Dolly Lenz, a broker with other listings there Just when it was first added to the list in 2023. “It was like America’s mayor chose this building – all very good things that were attributed to him because he lived in the same building,” she said. The tide had turned and the association in the current market “would be completely different,” she suspected at the time.

While it’s certainly poetic justice that the most salient symbol of Giuliani’s former power and privilege, in all his best Lenox Hill glory, goes to the two campaign workers whose lives he upended, it’s still New real estate York. “Ultimately, I think it’s going to take a while,” Garfield said.