After several missed deadlines and extensions, Rudolph W. Giuliani, the former mayor of New York, could be found in contempt of court on Friday for failing to deliver assets worth $11 million to two poll workers he defamed after the 2020 presidential election.
If he is held in contempt, he could face steep penalties, including jail time.
Mr. Giuliani, 80, was set to appear in federal court in Lower Manhattan to justify the stalled handover of some of his most prized possessions, including a penthouse apartment in Manhattan, a collection of Yankees memorabilia, luxury watches and a vintage Mercedes-Benz convertible. (It is unclear whether Mr. Giuliani will appear in person; his lawyers have indicated that he might attend the hearing remotely, citing health problems.)
The transfer was originally scheduled to take place in October, as a down payment on a $148 million judgment that he was ordered to pay to two Georgia election workers, Ruby Freeman and her daughter, Shaye Moss. Mr. Giuliani had claimed, without evidence, that the women had helped steal the presidential election from Donald J. Trump more than four years ago.
But one deadline after another has passed, and lawyers for the women said they have received only a fraction of the property.
Mr. Giuliani has argued that he has largely complied with the handover request and said that some of the items sought by the plaintiffs are not in his possession.
“The Court should see that I gave everything that I could give,” Mr. Giuliani wrote in a personal plea to the judge, Lewis J. Liman, on Christmas Eve.
But lawyers for the women said Mr. Giuliani continues to defy orders, despite repeated warnings from the court.
The plaintiffs have yet to receive legal possession of his 10-room apartment on the Upper East Side of Manhattan, 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 1980 Mercedes convertible, which he said was once owned by Lauren Bacall, has yet to be transferred.
And the whereabouts of a signed and framed Joe DiMaggio Yankees jersey, which once hung over Mr. Giuliani’s fireplace, are unknown, Mr. Giuliani has said. Lawyers for the plaintiffs said the item was removed from his apartment sometime before they gained access.
“It is hard to square Mr. Giuliani’s position with reality,” Aaron E. Nathan, one of the plaintiffs’ lawyers, wrote in a letter to the court on Dec. 30. “Enough is enough.”
The hearing marks a low point in Mr. Giuliani’s many legal battles stemming from his stint as Mr. Trump’s personal lawyer. In November, Mr. Giuliani’s lawyers withdrew from the handover case, citing an undisclosed professional ethics reason.
In a recently unsealed letter explaining their departure, one of the lawyers, Kenneth Caruso, said Mr. Giuliani 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.
On Wednesday, a lawyer for Mr. Giuliani requested that he be allowed to participate in Friday’s hearing remotely, because he was “having medical issues” related to his left knee, as well as breathing problems that he attributed to his time spent at the World Trade Center after the Sept. 11 attacks.
Judge Liman, who had a testy exchange with Mr. Giuliani about the handover delays in November, said he would not force Mr. Giuliani to appear in person, but that he would not consider his testimony otherwise.
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.
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