Giuliani was indicted, found liable for defamation and nearly bankrupt. Now he could land in jail

Trump’s former attorney faces threats of court-ordered sanctions in Manhattan and Washington, DC, Alex Woodward reports

Hours before a final deadline to answer why he should not be held in contempt of court for repeatedly lying about women he defamed, Rudy Giuliani was hit with yet another threat of contempt, in a separate court, by the same women.

“Severe” sanctions are warranted, they argued.

Donald Trump’s former attorney is now juggling motions against him in Washington, DC and in Manhattan, where he is also in the middle of a protracted legal battle to relinquish a long list of property and valuables to chip away at the nearly $150m he owes the mother-daughter duo.

The former New York City mayor — who falsely accused Ruby Freeman and Shaye Moss of manipulating election results in the volatile aftermath of the 2020 presidential election — is also a criminal co-defendant alongside the president-elect in Georgia, and among more than a dozen Trump allies facing criminal charges in a similar election interference case in Arizona.

Rudy Giuliani speaks to reporters on November 7 after leaving a federal courthouse in Manhattan, where a judge is enforcing a court order forcing him to turn over property to women he defamed (AP)

He filed for bankruptcy shortly after a jury determined he must pay the women $148m for his defamatory statements about them. A judge initially tossed his bankruptcy case, citing his lack of financial transparency and apparent attempts to evade court orders, leaving Giuliani’s lawyers and the people to whom he owes money trying to figure out how he would pay tens of thousands of dollars he owes in court fees, and whether he actually can pay any of it.

The parties ultimately agreed to dissolve the case, unfreezing a mountain of lawsuits against him.

Four months later, the 80-year-old former mayor faces the prospect of greater financial penalties, or even jail, after failing to keep up with — or purposefully trying to avoid — the ongoing legal fallout from election conspiracy theories that defined his spurious attempts to keep Trump in office in 2020.

The Independent has requested comment from a spokesperson for Giuliani.

He remains under a court order that prevents him from saying anything that resembles his defamatory statements.

But he has recently accused the women of “quadruple counting the ballots” and “passing hard drives that we maintain were used to fix” voting machines — echoing similar claims that landed him in a trial court for defamation last year.

His statements “repeat the exact same lies for which [he] has already been held liable, and which he agreed to be bound by court order to stop repeating,” attorney Michael Gottlieb wrote in a court filing in Washington, DC on November 20.

Giuliani missed a deadline to respond to the women’s demand for contempt. He sent a letter to the judge himself, two days after blowing the initial deadline, asking for a 30-day extension, because he needed “more time” to find an attorney.

He said four have turned him down.

Giuliani told the judge that his prospective attorneys believe she is “unreasonable” and “biased” against Trump, and that an outcome is a “foregone conclusion” and a “no-win proposition.”

A court sketch depicts Rudy Giuliani lashing out in a federal courtroom in Manhattan on November 26 (REUTERS)

On December 5, attorneys for the women filed a second contempt motion, this time in Manhattan, where lawyers for the defamed election workers say he has “not produced a single document” in response to court orders to turn over information about his Palm Beach condominium the women are trying to seize from him.

After a prolonged legal battle, Giuliani turned over his multi-million dollar New York penthouse apartment, a 1980 Mercedes Benz convertible, high-end watches and access to a storage facility where other valuables are stored.

But now “the time has come” for the court to hold him in contempt for violating what are now weeks-old court orders, and to “impose whatever coercive sanction it deems appropriate in its expertise,” according to the women’s attorneys.

They argue that a monetary penalty would not be insufficient. They did not rule out asking for jail time.

But giving Giuliani more time to “obfuscate in response to unambiguous discovery orders — especially when he has not provided any [indication] of an attempt to comply — risks jeopardizing” upcoming court dates, according to lawyers.

They have asked New York District Judge Lewis Liman to determine that Giuliani never planned to live at his Florida condo before he claimed it was his primary residence, and that he never intended to live there full-time until the proceedings against him — answers that would effectively resolve the central issues for a trial in the case set for January.

Rudy Giulaini, who joined the 2024 campaign trail to support Donald Trump, previously sought his help as he faced legal battles across the country (Getty Images)

In press conferences outside a Manhattan courthouse where Giuliani and election workers are navigating what he owes them, Giuliani has blamed his legal turmoil on what he believes is a Democratic conspiracy against him. He claims he is being “punished” by President Joe Biden’s administration for disseminating damaging information about his son Hunter.

Asked whether he is waiting for Trump to help him, he said “Trump doesn’t have to help me get out of it.”

“All Mr. Trump has to do is straighten out the legal system,” he said.

It is unclear whether Trump can help his former attorney once he returns to the White House.

Giuliani was struggling financially before the defamation ruling against him last year. He had put his Manhattan penthouse on the market and he began representing himself in several cases to save money on legal fees.

After his indictment in Georgia, he called on supporters to donate to a legal defense fund.

He reportedly made a desperate plea for Trump’s support during a meeting at Mar-a-Lago last year. The former president ended up hosting a fundraiser dinner; entry was $100,000 a plate.

Attorneys for Shaye Moss, left, and her mother Ruby Freeman, right, are asking federal judges in New York City and Washington, DC, to hold Rudy Giuliani in contempt of court (AP)

Last month, Giuliani asked the judge in his property turnover case to move a trial so that he could attend Trump’s inauguration. That was rejected.

“My client regularly consults and deals directly with President-elect Trump on issues that are taking place,” Giuliani’s attorney Joseph Cammarata told Judge Liman. “My client wants to exercise his political right to be there.”

Giuliani, while sitting inside the federal courthouse he helped open in 1996 when he was mayor, furiously clicked a pen while his attorney spoke to the judge. Then he spoke up for himself.

“The implication you make is against me, and every implication against me is wrong,” he told the judge.

“I’m not impoverished,” he said. “Everything I have is tied up. I don’t have a car. I don’t have a credit card. I don’t have cash.”

The next time he speaks up, Judge Liman said, “The court will take action.”