The items read like a treasure trove of riches for New York royalty.
A 10-room apartment in a luxury cooperative one block from Central Park. A vintage convertible once owned by Lauren Bacall. Joe DiMaggio’s No. 5 Yankees jersey, signed and framed.
On Tuesday, the owner of these valuables, Rudolph W. Giuliani, 80, must surrender them all, and more, to two election poll workers in Georgia, whom he defamed and who won a $148 million judgment in a lawsuit.
The order, by a Federal District Court judge last week, is an epilogue of sorts. Mr. Giuliani was once a widely beloved mayor who fashioned himself as the quintessential New Yorker. He was a leader respected far beyond the city before ultimately aligning himself with Donald J. Trump and promoting election conspiracy theories that cost him his reputation, his vocation and his broad appeal.
Mr. Giuliani now stands to lose something just as precious — his carefully curated New York identity, built over decades in the spotlight, one trophy at a time. For a Brooklyn-born power broker, whose legal troubles have stripped him of his last home in the city, it approaches exile.
Mr. Giuliani has cited the court order in a fund-raising email for his legal defense.
“They want my home, my belongings, even all of the nostalgic keepsakes that I’ve collected throughout my 80 years of life,” he wrote in the letter, before adding he will “NEVER SURRENDER the fight.”
Still, the fire sale begins now.
Mr. Giuliani was found liable for defaming Ruby Freeman and her daughter, Shaye Moss, two election poll workers who he claimed tried to steal the 2020 election from Mr. Trump. The women faced threats of violence and racist smears after Mr. Giuliani mentioned them repeatedly in media appearances. Mr. Giuliani, a former federal prosecutor in the 1980s, also faces criminal charges in two states for his attempts to keep Mr. Trump in office.
A path to seize Mr. Giuliani’s assets, worth about $10 million, was cleared this summer. In late 2023, a jury awarded Ms. Freeman and Ms. Moss the $148 million judgment. Mr. Giuliani filed for bankruptcy soon after, but failed to comply with basic court requirements.
Last Tuesday, a judge gave Mr. Giuliani one week to put the bulk of his possessions in a receivership controlled by the two women, who are likely to try to sell the items quickly.
Mr. Giuliani “is being unfairly punished by partisan, political activists who are trying to make an example out of him,” Ted Goodman, his spokesman, said in a statement last week.
Lawyers for Ms. Freeman and Ms. Moss did not respond to request for comment.
Mr. Giuliani has been ordered to hand over nearly his entire estate, except, for now, his home in Florida, and three World Series Yankees rings that he claims to have given to his son, Andrew.
The list of Mr. Giuliani’s belongings includes 26 designer watches. Two were given to him as gifts by the presidents of France and Italy for his leadership after the Sept. 11 terrorist attacks, according to court documents.
Another timepiece, inherited from his grandfather, Rudolfo, must also be forfeited.
There is his collection of sports memorabilia, including a signed photo of the Yankees legend Reggie Jackson, known as Mr. October for his heroics in postseason play. The Joe DiMaggio jersey, from 1951, the last active season for the Yankees great, hung above the wood-burning fireplace in Mr. Giuliani’s library, where he recorded political podcasts.
Todd Sawatzky, a sports memorabilia appraiser in Niagara Falls, Canada, said that such a rare jersey could sell for over $10,000, but exponentially more if it was a game-worn shirt.
There is the 1980 Mercedes-Benz 500 SL, with 80,000 miles on it, which Mr. Giuliani said in October was his last remaining vehicle. (His driver’s license is expired, he said in court.) He claimed the car was owned by Ms. Bacall, the film and Broadway star who lived for decades at the Dakota, one of New York’s most storied apartment buildings.
Mr. Giuliani bought the car for $20,000, he said in the filings, because it made him feel like Humphrey Bogart, one of the great leading men in American cinema and Ms. Bacall’s first husband.
“It was the quintessential, expensive, sort of playboy car,” Tony Quiroga, the editor in chief of Car and Driver, said.
Then there is the fight over three Yankees World Series rings. George Steinbrenner, the team’s mercurial late owner, had the rings made for Mr. Giuliani after three of the team’s four championships during his time as mayor. Mr. Giuliani has claimed that he gave them to his son, Andrew and the rings are, for now, not subject to the seizure. In a phone call, Andrew Giuliani declined to comment, because litigation is ongoing.
Each is distinctive. The 2000 World Series ring, representing the Yankees’ third win in a row, is made of 14-karat gold with the words “World Champions” surrounding a diamond-encrusted “NY” on a blue sapphire. In 2020, a similar ring, made for the former Yankee Chuck Knoblauch, was valued at between $40,000 to $60,000.
But the crown jewel of Mr. Giuliani’s assets is the 10th-floor, three-bedroom aerie at 45 East 66th Street, a landmark co-op building on the Upper East Side. Mr. Giuliani moved into the apartment with his ex-wife, Judith Giuliani, in 2002, not long after being hailed as “America’s mayor” by Oprah Winfrey for his stirring leadership after the Sept. 11 attacks.
Much has changed since. In 2021, federal agents raided the apartment as part of an investigation into whether Mr. Giuliani had broken lobbying laws while serving as President Trump’s personal lawyer.
In 2023, Mr. Giuliani listed the apartment for $6.5 million; a year later, he cut the price by 20 percent, which reflected poorly on the exclusive co-op, real estate brokers said. It was taken off the market in early October. Until a few weeks ago, the apartment was still Mr. Giuliani’s primary residence
“The vibe has been horrific for quite a while” in the building, because of the negative publicity that Mr. Giuliani attracts, said Dolly Lenz, a real estate agent who has sold apartments in the building. The roughly 30-unit, prewar tower is home to a number of wealthy but otherwise low-profile residents, including bankers and diplomats.
The co-op board has prohibited residents from speaking publicly about Mr. Giuliani’s recent departure from the building, according to building tenants.
The notoriety alone could have already affected the pricing of other apartments, Ms. Lenz said.
Some neighbors were vocal in their lack of sympathy for Mr. Giuliani.
“It couldn’t happen to a better guy,” Judith Byrd, one of the few rent-stabilized tenants in the building, said.
Not everyone agreed. Fred Stuart, a publicist and longtime renter in the building, said he exchanged niceties with Mr. Giuliani just a few weeks ago in the elevator.
“He’s very likable,” he said, adding that he should be granted some grace. “He did a lot for the city, and we shouldn’t forget it.”
What comes next for the apartment is unclear. If Mr. Giuliani successfully appeals the court’s decision, a potential sale could be slowed or halted by the litigation, Michael Romer, a real estate lawyer, said. And if it does sell, part of the proceeds would most likely have to be paid to other creditors, he said.
“Who would really want to buy this property now, given all that is happening?” he asked.
Mr. Giuliani’s only other apartment, a condo in a pink midcentury complex in Palm Beach, Fla., could soon be subject to a similar seizure.
He has a January court date to determine if he can claim the Florida apartment as his primary residence, to spare it from creditors.
Some have already noticed Mr. Giuliani’s absence. John Sotello, a service captain at Bar Italia, a bistro near the former mayor’s building, said Mr. Giuliani used to stop in unannounced and take pictures with diners.
“We miss him,” he said. “As a person, as a politician and as a customer.”
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