
(Photo by Drew Angerer/Getty Images)
Rudy Giuliani’s litigation strategy is… unique. It’s kind of like National Geographic, but if the wildebeest ran directly into the mouth of the lion every time. This is a guy whose utter refusal to do paperwork earned him a $148 million default judgment in the defamation case filed by Ruby Freeman and Shaye Moss, the Atlanta poll workers he falsely accused of tabulating fraudulent ballots in 2020. Then he stumbled into and out of bankruptcy after discovering that you actually do have turn over your financial information if you want the protection of the court. Who knew! And in DC, he’s currenlty daring Judge Beryl Howell to hold him in contempt because he refuses to keep Freeman and Moss’s names out of his mouth.
But the real action this week is in New York, where Rudy is facing yet another potential contempt finding in the collection action, as well as possible death penalty sanctions for (say it with us) failing to cooperate with discovery and hand in his homework. That case involves Rudy’s desperate effort to hang onto his Florida condo under the state’s generous homestead exception, despite the fact that he did his daily podcast from New York during most of the year in question. Notably his prior counsel noped out rather than do whatever it was Rudy was asking them do in that case.

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Yesterday, Judge Lewis Liman signed an order to show cause why Rudy should not be held in contempt in the collection action, instructing him to file a response by Christmas Eve and show up in person on January 3 to explain himself. The court granted Freeman and Moss’s motion, detailing his total failure to turn over his property, after being warned that something very bad would happen if he didn’t.
Consider this amazing exchange from a status conference on November 7 where Rudy’s prior counsel admitted that his client had made no efforts to comply with an October 22 turnover order:
THE COURT: Isn’t the right approach to that, I’ve ordered your client to turn over all of this property, and your client consented to, said he had possession of all of this property at the time that I entered the order. Procedurally, he doesn’t have a choice but to comply. If it becomes impossible for him to comply, then the plaintiff moves for contempt, your client gets on the stand, and he goes through all of the efforts that he made to get it and why he was frustrated. It strikes me as kind of hard to believe that your client would not be able to get somebody at the storage facility to open up the storage facility to get his property. It’s not clear to me what efforts he’s made.
MR. CARUSO: I’ll tell you what efforts we’ve made.
THE COURT: No. What efforts he made.
MR. CARUSO: He didn’t make any efforts other than what I made.
THE COURT: Okay. That’s kind of — you might consider your words, because it does play into what will happen if there were a contempt proceeding against him.
On November 22, the judge issued another order in which he instructed Giuliani to hand over his stuff by December 15 “on pain of contempt.”

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Since then, Giuliani’s efforts have been uneven at best. He surrendered the Mercedes he claims once belonged to actress Lauren Bacall, but not the title. He vacated his apartment, but failed to give the plaintiffs the keys or the deed, and seems not to have bothered trying to take his ex-wife’s name off the place. In response to instructions to hand over specific items of sports memorabilia, he vaguely gestured in the direction of the “America First Warehouse” in Ronkonkoma, New York, where his personal items are packed away in opaquely labeled boxes.
Rudy’s new counsel is a flamboyant divorce lawyer name Joseph Cammarata. His first move was to hold a press conference outside the offices of the plaintiffs’ counsel to decry the “lawfare” against America’s Mayor. Then he asked the court to delay the January 16 trial so that Rudy could spend that week in DC at inauguration parties. Judge Liman responded that he was happier to entertain a motion to move the trial up to the week of the 10th, if the defendant was so inclined. (He was not.)
On December 8, roughly five weeks after the November 4 deadline for disclosures, Giuliani informed the plaintiffs that he would be calling five new witnesses to testify that he really did live in Florida, not New York. Unsurprisingly, the plaintiffs were not impressed, particularly since one of those witnesses is Rudy’s girlfriend/cohost/emotional support weirdo Dr. Maria Ryan, who has been ducking process and who was the subject of a (since granted) motion to compel.
Judge Liman instructed the defendant to respond by Tuesday, December 17.
“Defendant shall indicate whether he will arrange for the five additional witnesses to receive subpoenas and to be made available for deposition on or before January 9, 2025, including when and where the witnesses will be made available for in-person depositions,” he wrote. “Defendant shall also indicate whether he will arrange for the responsive documents of each of the witnesses to be produced to the Plaintiffs at least one week prior to deposition.”
Cammarata did indeed respond… sort of. But we will not be linking to the document, which included the witnesses’ personal contact information. Cammarata represented that he will not be calling two of the five new witnesses at trial. But he produced yet another new witness, one Monsignor Alan Placa, who can shed light on Rudy’s living situation.
A quick Google search reveals that the Monsignor presided over Giuliani’s first wedding in 1968, as well as its subsequent annulment. In 2002, he was placed on administrative leave due to sexual abuse allegations, which were substantiated by grand jury testimony from multiple men who accused him of molesting them as teenagers. Rudy then hired Placa through one of his companies. The church held the investigation open until 2009, which was long enough that Placa’s official exoneration and his retirement could take place simultaneously.
Cammarata informed the court that Placa will testify at the January 16 trial, as will Rudy’s other witnesses, Maria Ryan, Michael Ragusa, and Ryan Medrano. He says that Ryan, Ragusa, Medrano, and Placa are amenable to being deposed. He did not say when or where such depositions might take place, and made no representations about document production.
This would seem to fall somewhat short of satisfying the court’s order. But if the bet is that Rudy’s going to get defaulted anyway, or barred from presenting any of this evidence, then perhaps it won’t matter in the end.
Freeman v. Giuliani [Collection Docket, via Court Listener]
Freeman v. Giuliani [Homestead Docket, via Court Listener]
Liz Dye lives in Baltimore where she produces the Law and Chaos substack and podcast.