A federal judge on Thursday, having grown exasperated with Rudy Giuliani, said he had heard enough excuses.
“What can be delivered right now?” Judge Lewis J. Liman asked, after peppering lawyers for Mr. Giuliani, the former mayor of New York City, with questions about some of his most prized possessions, among them a signed Joe DiMaggio jersey; 26 designer watches; and a vintage Mercedes-Benz.
Those items, and more, were supposed to be handed over last week to begin paying off a $148 million judgment to two former Georgia election workers whom Mr. Giuliani had defamed. The deadline came and went, and still nothing was turned over.
On Thursday, the judge set the latest “final” deadline, brushing aside repeated arguments that the possessions should remain with Mr. Giuliani while the case was under appeal. By the end of next week, he said, Mr. Giuliani had to either hand over all the items, or he could face civil contempt, a charge that could carry severe penalties, including possible jail time.
The testy exchange was the latest twist in a wild-goose chase that has sent the plaintiffs’ lawyers searching for assets at a luxury co-op on the Upper East Side, a condo in Palm Beach and a remote storage unit in Ronkonkoma, a hamlet on Long Island two hours outside of Manhattan.
Ruby Freeman and her daughter, Shaye Moss, the former election workers, sued Mr. Giuliani for defamation in 2021, after he claimed, without evidence and on several occasions, that they had tried to steal the presidential election four years ago from Donald Trump. The women, who are Black, faced racist smears and death threats.
Late last year, a jury awarded them $148 million for the harm they suffered. Faced with mounting debts, Mr. Giuliani filed for bankruptcy, but, because he refused to comply with basic court requirements, the case was dismissed, leaving his assets vulnerable to his many creditors.
The most valuable item is Mr. Giuliani’s longtime home, a 10th-floor apartment near the top of a white-glove cooperative building at 45 East 66th Street in Manhattan. It was last listed in October for $5,175,000, down from an original price of $6.5 million.
Lawyers discovered that Mr. Giuliani had failed to update paperwork in connection with the apartment after his divorce from his wife, Judith Giuliani, stalling the transfer.
Mr. Giuliani, who entered the courtroom in Lower Manhattan on Thursday in a pair of thick-rimmed sunglasses, a navy suit and a red-white-and-blue tie, shook his head and grimaced throughout the hourlong hearing, occasionally fiddling with a large ring. It was unclear if the ring was part of the assets to be surrendered.
His lawyer argued that forcing his client to surrender a watch given to him by his grandfather was “vindictive.”
“Oh, come on, that’s ridiculous,” the judge said, his voice rising. “Bodega owners have family heirlooms,” he said, referring to another case he has presided over — “and if they have a debt, they have to pay the debt.”
He added, “The law is the law.”
On Halloween, when the lawyers for Ms. Freeman and Ms. Moss were granted access to the apartment, they said they discovered that Mr. Giuliani’s most valuable items — luxury furniture, art and Yankees collectibles — had been moved weeks earlier.
At the hearing, Kenneth Caruso, a lawyer for Mr. Giuliani, confirmed that many of the items had been put into storage in the Long Island facility, but he could not specify exactly which ones. Other items, including several watches and a 1980 Mercedes-Benz convertible, are at or near Mr. Giuliani’s Palm Beach condo, he said.
Mr. Giuliani has claimed that he doesn’t recall what is in storage, and efforts to get a full inventory from the Long Island facility owner have not been successful, the lawyers said.
“We’ve asked over and over where the stuff is,” Aaron Nathan, a lawyer for the two women, said.
“The notion that your client doesn’t have any knowledge of where his assets are located is farcical,” Judge Liman said, addressing Mr. Giuliani’s lawyers.
Mr. Caruso charged that the plaintiffs were seeking an inventory of items only to “entrap” Mr. Giuliani into making false statements.
Mr. Giuliani has claimed that the Mercedes-Benz convertible was once owned by Lauren Bacall, the Hollywood starlet. On Election Day, in Palm Beach, Mr. Giuliani was seen cruising in the passenger seat of a car that matched its description.
Even though the vehicle had already been included in the list of assets to be surrendered, Mr. Giuliani’s lawyers argued that it was exempt because it was worth less than $4,000. But the vehicle regularly sells for $15,000 or more on the open market, according to car experts.
Other items could also be at risk of seizure. Mr. Giuliani is arguing that his Palm Beach condo should not be subject to the order, because of a state exemption. Mr. Giuliani’s son, Andrew, has said that a collection of World Series Yankees rings made for his father should not be included, because they were given to him some years ago.
Lawyers for the two women also raised the question of a recently discovered limited-liability company that Mr. Giuliani appears to have a stake in. Mr. Caruso quipped that a bank account with about $3,000 was also being pursued.
“It’s real money to me,” Judge Liman shot back.
Mr. Caruso vowed to appeal the defamation case decision to the Washington, D.C., circuit court.
As Mr. Giuliani left the courthouse, he struck a defiant tone, denying that he had defamed the women.
“The reality is that this case is obviously a political vendetta,” he said, before insisting that he will cooperate with the new deadline.
Before ducking into the back seat of a gray Lincoln S.U.V., he made a rueful allusion to Mr. Trump’s election win.
“Mr. Trump doesn’t have to help me get out of it,” he said. “All Mr. Trump has to do is straighten out the legal system. Then you’ll find out who the real criminals are.”
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