Rudy Giuliani, the disgraced politician once known as “America’s Mayor” and now known as a punchline, is about to face the most disastrous court ruling of his life—and it will only get worse from there.
Giuliani is poised to get hit with a multimillion dollar ruling against him in D.C. over his baseless accusations of election fraud against two poll workers. After that civil trial concludes, he’ll turn around and begin preparing for a criminal trial in Atlanta, where he’s facing many of the same racketeering charges he once wielded as a federal prosecutor against mobsters in New York. And throughout it all, Giuliani has a long list of creditors, from former associates to contractors, who are also hounding him for money.
For Giuliani, 2023 will likely end in penniless defeat. But 2024 could be even worse—it could actually end with him in prison.
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At the moment, the most immediate problem for Giuliani is his defamation suit. A jury in the nation’s capital has spent all week hearing about how the conspiracy-crazed attorney ruined the lives of two Georgia poll workers, Ruby Freeman and Shaye Moss, a mother and daughter whom Giuliani falsely accused of secretly plotting to sabotage Donald Trump’s 2020 re-election campaign.
Giuliani, an associate attorney general in the 1980s, managed to screw up the court case by barely putting up a defense—and getting hit with sanctions for failing to turn over evidence. As such, the damages-only trial has portrayed Giuliani, the former legal chief of the Southern District of New York, as a monster without compunction, one who should pay anywhere from $15.5 million to $43 million for abusing his status and MAGA megaphone to harness unfounded rage in the wake of Trump’s 2020 loss.
On Tuesday, Moss testified in the D.C. courtroom about the overwhelming fear of her son “finding me and my mom hanging in front of our house,” describing Trump supporter threats as a revival of the white supremacist vengeance that haunted the American South for a century. On Wednesday, her mother detailed the deluge of death threats that flooded her life after Trump tweeted out her name—all thanks to the target Giuliani painted on her back.
“They was coming to get me,” Freeman testified, according to journalists Brandi Buchman, Anna Bower, and others in the courtroom.
Giuliani, the 79-year-old who once led an emotionally devastated New York City through the Sept. 11 terrorist attacks as mayor, could have apologized publicly. He could have remained silent and followed the directives his agents gave so many mafiosos in Manhattan.
But no. Giuliani, a failed presidential candidate, dug an even deeper hole for himself—pissing off the judge and potentially opening himself up for even bigger damages by somehow defaming the women yet again just outside the courthouse after the first day of trial.
“They were engaging in changing votes,” Giuliani insisted when speaking to reporters on Monday. “When I testify, the whole story will be definitively clear that what I said was true, and that, whatever happened to them—which is unfortunate about other people overreacting—everything I said about them is true.”
Giuliani, a former LifeLock spokesperson, got a tongue-lashing the very next day from U.S. District Judge Beryl Howell, who warned that his recalcitrant remarks “could support another defamation claim.”
Never one to learn his lesson, Giuliani took to his right-wing talk radio show on Tuesday night to deliver yet another sermon dripping with unexplained “coincidences”—this time spinning the trial as a sinister leftist plot.
Giuliani noted that Freeman and Moss claim to be borderline destitute while simultaneously being represented by extremely expensive attorneys at the esteemed D.C. law firm of Willkie Farr & Gallagher, something that Giuliani chalks up to a tenuous connection between the women’s lead lawyer, Michael J. Gottlieb, and the current president’s son, Hunter Biden, who has long been the target of Giuliani’s ire. (As The Daily Beast has previously reported, Gottlieb worked with Biden back in 2014, where they handled business related to the Ukrainian natural gas company Burisma.)
Rudy Giuliani talks to reporters as he exits U.S. District Court.
Leah Mills/ReutersDecrying “politics,” Giuliani implied that his current case is merely the Democrats’ revenge for the way he successfully made the Hunter-laptop-and-Burisma scandal the rallying cry of Fox News and the MAGA world.
It’s conspiracies everywhere you look. But Giuliani, Trump’s personal attorney during his efforts to overturn the 2020 election, is clearly rattled enough to start watching his language.
“Today was the second day of my trial, involving, um, involving, uh, the people that were engaged at the State Farm Arena,” he said on Tuesday night during a stream of his 297th episode of America’s Mayor Live, this time broadcasting in Washington, D.C. “I think I’ve made enough comments on it, so now that we’re down to the last couple of days of the trial, discretion is probably the better part of valor.”
And yet he remains aloof.
“I shouldn’t go into great detail about the substance of the case, which might or might not violate… I guess the stipulation? Hmm. Maybe the order she entered today. I’m not sure. I haven’t looked at it,” Giuliani said during the livestream, rubbing the side of his face as the camera began to comically zoom in.
But his reaction to the impending doom is telling, with Giuliani resorting to incredulous humor about the entire affair.
“They’re seeking $40 million dollars,” Giuliani said on his nightly, live video podcast, laughing awkwardly with raised eyebrows and a nod of disbelief. “Oh yeah.”
There’s no sign that Giuliani has the money—or even a fraction of that. Old debts keep surfacing in New York court documents every few weeks since September, with one lawsuit after another calling him out as a deadbeat. He has apparently refused to pay his longtime associate and personal lawyer Robert Costello some $1.3 million for years of research and legal representation. He couldn’t even close out a $30,000 phone bill. Just last month, the accountants he hired to help him through his divorce came after him for an outstanding $10,000.
The idea that Giuliani—who previously worked as an unregistered lobbyist appealing to officials in countries like Romania and Ukraine—is underwater and stiffing contractors isn’t new. In August 2020, art adviser and TV personality Miller Gaffney sued him for $15,700 after he allegedly failed to pay her for appraising the estranged couple’s art collection during their split.
But the difference is that now, Giuliani has a lot more to lose. Those lawsuits are making their way through New York state courts, where state judges could start to make rulings on those relatively simple claims in the coming months. If Giuliani doesn’t settle them out of court, the legal battles threaten to expose the extent of his upside-down finances in public.
However, the real danger comes in the latter part of next year, when Fulton County District Attorney Fani Willis seeks to put Giuliani on trial along with former President Donald Trump for trying to overturn the 2020 election in Georgia.
Giuliani faces years behind bars if convicted of essentially taking part in a shakedown of the state’s election system. And yet, the clear way out already taken by others in the case—flipping and becoming a state witness to help prosecutors nail Trump—pits Giuliani against himself. That’s because he’s openly shown himself to be financially dependent on Trump’s massive fundraising.
Look no further than the $100,000-a-plate “Dinner With America’s Mayor” that Trump hosted at his golf course in Bedminster, New Jersey, in September. Were Giuliani to turn on Trump, as other MAGA lawyers like Kenneth Chesebro and Sidney Powell already have done, the Trump money spigot would instantly dry up.
The Giuliani downfall has been slow but precipitous: 2021 saw the ruining of his professional reputation, with New York and the District of Columbia suspending his law license for spreading lies and for his role in the Jan. 6 insurrection. This year exposed his financial ruin. Next year, it could be prison.
Prosecutors in Fulton County are asking for the massive racketeering trial to start in August, but jury selection is expected to take weeks. Last month, DA Willis revealed that she expects the historic trial to stretch through next winter. Giuliani will be in the hot seat alongside the former president he pledged loyalty to—and anyone else who hasn’t struck a plea deal by then.
