Rudolph W. Giuliani, the former mayor of New York, was grilled for hours in federal court on Friday after missing several deadlines to hand over $11 million of his prized possessions to two poll workers he defamed after the 2020 election.
Mr. Giuliani avoided, for now, being held in contempt of court — a charge he has been threatened with at various times during the case and that could include jail time.
But for most of his time on the stand, Mr. Giuliani frustrated the judge and the plaintiffs’ lawyers with a spotty memory and vague answers that slowed to a crawl proceedings that were already bogged down in minutiae.
For much of the seven-hour hearing, lawyers on both sides were preoccupied with the question: Where have you gone, Joe DiMaggio?
One of the central items of Mr. Giuliani’s collection of sports memorabilia is a jersey signed by Mr. DiMaggio, the Yankees legend, that hung over the former mayor’s fireplace. On Friday, Mr. Giuliani said he had no idea where it was.
That was not the only missing Yankees great.
“There is no Reggie Jackson picture,” Mr. Giuliani said, referring to the right-fielder known as Mr. October. He had previously said in court documents that the picture would be handed over to the plaintiffs. But now, the photo didn’t exist, according to Mr. Giuliani. “The picture was Derek Jeter,” he said. “I was kind of confused about it.”
The judge, Lewis J. Liman, appeared skeptical of Mr. Giuliani’s puzzlement, noting that such a rare collectible, especially for an avowed Yankees fan, would be top of mind.
“I’m sorry,” Mr. Giuliani said in response to questions about the collectibles, and a number of other items that were expected to be found in his New York apartment. “When I looked, this is what I found.”
At the heart of the contempt charges he continues to face is whether Mr. Giuliani, 80, has been uncooperative with the handover of his personal assets, which will serve as a small down payment on the $148 million defamation judgment that he owes the plaintiffs, Ruby Freeman and her daughter, Shaye Moss. Mr. Giuliani said, repeatedly and without evidence, that the women helped steal the presidential election from Donald J. Trump more than four years ago.
The assets include a 10-room apartment on the Upper East Side of Manhattan; a 1980 Mercedes-Benz convertible; a collection of 26 designer watches; and rare Yankees collectibles, the most valuable of which might be the signed and framed DiMaggio jersey.
More than two months after a federal court judge ordered Mr. Giuliani to hand over the items, the former mayor and his lawyers contend that he has tried to comply fully, but that the process has been onerous.
“Mr. Giuliani is an 80-year-old man who has been hit by a whirlwind of discovery,” said Joseph M. Cammarata, Mr. Giuliani’s lawyer, who specialized in divorce cases before joining the defense team. Mr. Giuliani is also facing civil and criminal charges in other cases, stemming from his time as Mr. Trump’s personal lawyer.
In roughly three hours on the stand on Friday, Mr. Giuliani repeatedly responded that he could not remember details about his personal items or their whereabouts.
While pressing Mr. Giuliani, Meryl Governski, one of the lawyers for the plaintiffs, turned her attention to a checking account subject to the seizure.
“Where does it say that you turned over the cash?” she asked Mr. Giuliani, pointing out an omission in a recent letter he wrote to the court.
Mr. Giuliani, flipping through a bulky binder of materials, appeared flustered. “Are we talking about the Mercedes now?” he said.
As the hearing dragged on, lawyers on both sides seemed to test Judge Liman’s patience. After a long series of objections by Mr. Cammarata, nearly all of them overruled, Judge Liman chastised the defense.
“If you have one more speaking objection, sir, you’re going to have to sit down,” he said. “You know the rules.”
On Thursday, Mr. Giuliani’s lawyer asked if his client could appear virtually, because of medical issues related to his left knee, as well as breathing problems attributed to Mr. Giuliani’s time spent at the World Trade Center after the Sept. 11 attacks.
But Judge Liman, who had a testy exchange with Mr. Giuliani about the case in November, said he would not accept Mr. Giuliani’s testimony unless he attended in person. So the former mayor, in a dark blue suit and glasses, walked into the 15th floor courtroom on Friday with a visible limp and a dry cough.
The transfer was originally scheduled to take place in late October. But one deadline after another has passed, and lawyers for the women said they have received only a fraction of the property.
The women have yet to receive legal possession of Mr. Giuliani’s apartment, once listed for over $6 million, in part because paperwork has not been updated since his divorce from his ex-wife Judith Giuliani, according to court filings. The title to Mr. Giuliani’s convertible, which he said was once owned by Lauren Bacall, has yet to be transferred.
But Mr. Giuliani raised eyebrows on Election Day, when he appeared in the passenger seat of the same convertible, more than a week after the initial turnover deadline. On Friday, he said he has requested a copy of the title to the car three times, but has yet to receive it.
In November, Mr. Giuliani’s original lawyers withdrew from the case, citing an undisclosed professional ethics reason.
In a recently unsealed letter explaining their departure, one of the lawyers, Kenneth Caruso, a longtime friend of Mr. Giuliani, said his client was not cooperating in the discovery process related to a condominium he owns in Palm Beach, Fla., and was withholding access to his electronic devices.
The judge will determine on Monday whether Mr. Giuliani was uncooperative during the discovery process. A separate hearing will be held to discuss his turnover efforts.
Later this month, Mr. Giuliani also faces the possibility of contempt charges in a Washington, D.C., court, where he has been accused of continuing to publicly make false claims about the two Georgia poll workers.
On Jan. 16, Mr. Giuliani is expected back in court to argue that his Palm Beach condo, as well as three personalized Yankees World Series rings, should be excluded from the handover.
Outside the courthouse, at a prepared mic stand, Mr. Giuliani, who typically appeared energized and combative, demurred.
“It would be inappropriate and unwise to say a darn thing about this case right now,” he said.
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