Rudy Giuliani Faces A Month Of Legal Reckoning

NEW YORK — Rudy Giuliani’s legal problems are about to get even worse.

Two federal judges are mulling whether to hold him in contempt — a punishment that could potentially include throwing him jail — for defying court orders. And the former New York City mayor is facing a trial later this month about whether he must turn over his Palm Beach condo to two Georgia women who won a $148 million defamation verdict against him in 2023.

Giuliani also remains under criminal indictment in Arizona and Georgia for his efforts to help Donald Trump subvert the 2020 election. He has been disbarred in New York and Washington, D.C. But so far, his biggest legal burdens have stemmed from the civil judgment in the defamation case.

The women who won that judgment — former election workers Ruby Freeman and Shaye Moss — have already taken possession of much of Giuliani’s property, including watches, a ring and a vintage Mercedes-Benz convertible. The former New York City mayor is in the process of turning over his Manhattan apartment, too. But he has fought the collection efforts tooth and nail, and he has even continued to denigrate Freeman and Moss.

Along the way, he has frustrated two federal judges, who have repeatedly chafed at his resistance to their commands, and who now have the power to punish him for his intransigence — with fines, jail or other efforts to legally “coerce” his compliance.

First up is a hearing in Manhattan federal court on Friday in which Judge Lewis Liman will weigh a request by Freeman and Moss to hold Giuliani in contempt and impose “severe” sanctions on him. The Georgia women — who are mother and daughter — won the nine-figure defamation judgment against Giuliani when a jury found that he falsely accused them of election fraud after the 2020 election. They say Giuliani has repeatedly thwarted Liman’s orders related to the transfer of his assets as they seek to collect the judgment.

In particular, they say, he has failed to turn over even a single document in response to court orders requiring him to share information about his Palm Beach condo, which Freeman and Moss are trying to seize.

Giuliani has a second contempt hearing on Jan. 10 — this time in Washington in front of Judge Beryl Howell, who presided over the defamation trial in December 2023. Freeman and Moss are asking Howell to hold Giuliani in contempt for violating an agreement not to make new defamatory claims about them. They say Giuliani renewed his false attacks during two recent podcast appearances.

Freeman and Moss have not explicitly asked for jail time, but they have said that any fine would be an insufficient punishment, because Giuliani’s debt to the two women already far exceeds his assets.

In Liman’s courtroom, they have urged the judge to impose “whatever coercive sanction” he “deems appropriate.” One punishment they proposed is a formal ruling from Liman that Giuliani’s failure to produce documents about the Palm Beach condo amounts to an admission that he didn’t intend to live in it before he claimed it was his primary residence and that he didn’t live there full time. Such a ruling would essentially resolve the main issue set to be determined at a trial set for Jan. 16, and it would render Giuliani in jeopardy of having to forfeit the condo to the women.

In court filings, Liman has appeared dismissive of Giuliani’s explanations and arguments regarding his failure to provide documents. And the judge has already signaled that Friday’s contempt hearing may not go well for Giuliani.

For his part, Giuliani has done little to win Liman’s favor. In a court hearing in November, Giuliani erupted at Liman after the judge questioned his efforts to turn over the required property. And his lawyers suggested in court documents that the judge — a Trump appointee — might be biased against Giuliani because 29 Republicans voted against Liman’s confirmation.

On Thursday afternoon, Giuliani asked Liman to let him appear at Friday’s hearing by Zoom, rather than in person, saying that he was dealing with knee issues and a cough that stemmed from his presence at the site of the World Trade Center attack on Sept. 11, 2001.

Giuliani, notably, has made multiple TV and podcast appearances over the last few days, including Wednesday evening when he spoke at length on Newsmax about the mass attack in New Orleans. He also recorded a two-hour podcast on the subject the same day.

In an order Thursday evening, Liman said Giuliani will have to come to court in person if he wants to testify in the proceeding.

Giuliani’s pain won’t end with the New York hearing. A week later, he’s scheduled for the contempt hearing before Howell — another judge whom Giuliani has repeatedly antagonized. He has attacked her as biased because of her handling of dozens of cases stemming from the Jan. 6, 2021, attack on the Capitol, and he has claimed that he struggled to find a lawyer willing to represent him in her courtroom.

Howell, an appointee of Barack Obama, has rapped Giuliani repeatedly over the past two years for defying her orders — a history that could come back to haunt him during the contempt hearing.

Both contempt hearings could be a prelude to Giuliani’s Jan. 16 trial before Liman on the status of the Palm Beach condo — and whether that condo qualifies for a so-called “homestead” exemption from collection efforts.

The trial is also set to cover the fate of his beloved New York Yankees World Series rings. Giuliani claims he gifted them to his son Andrew years ago, making them off limits to Freeman and Moss. And he has produced photos and text messages to back up his claim. The trial could force both Giuliani and his son onto the witness stand to spell out the details of the transfer.

Orden reported from New York. Cheney reported from Washington.