Join us Read
Listen
Watch
Book
Sensemaker Daily

Will Rudy Giuliani die in jail for Donald Trump?

Will Rudy Giuliani die in jail for Donald Trump?
The former mayor of New York is in need of a good lawyer and reportedly broke. Georgia prosecutors are trying to persuade him to turn against Trump in court

Rudy Giuliani, Trump’s former personal attorney, has lost one of his own lawyers and is said to be broke.

So what? The outcome of two criminal cases against Trump for trying to steal the 2020 election could hinge on the former New York mayor who became the hero of 9/11. Prosecutors are trying to persuade him and others to turn against Trump in court, and the more desperate Giuliani’s personal situation becomes, the more likely he may be to “flip”.

Giuliani is already

  • known to have urged the crowd that invaded the Capitol in the January 6th insurrection to engage in “trial by combat”;
  • accused in Georgia of masterminding a scheme to overturn the election with “fake electors” and of promoting lies about voter fraud in Michigan, Arizona and Pennsylvania; and
  • 79 years-old and at risk of dying in jail if convicted.

His fall from grace is the subject of Trump & Rudy, a Tortoise podcast series starting today.

And now… David Wolfe, one of his lawyers in the Georgia case, has filed notice that he plans to withdraw, while Giuliani’s biographer describes him as “penniless”.

The caveats. Giuliani denies all wrongdoing in the Georgia case. His spokesman has said there’s no chance of him flipping against Trump because the only information he has supports the ex-president’s contention that the election was stolen. And in any case, every effort so far to hold Trump to account for January 6th has only helped him in the polls. 

The money. That said, Giuliani’s personal fortunes have hit a nadir. He has an income from a radio show he hosts in New York, which he supplements by hiring himself out for online conversations with his fans. But:

  • He’s being sued for $1.4 million in unpaid legal bills by his own lawyers, who say he has paid only $214,000 of what they are owed.
  • He’s been forced to put his New York apartment on the market (for $6.5 million) and to beg Trump to pay him for years of so far unpaid work as his lawyer.
  • He faces substantial damages in a defamation case brought by two Georgia election workers whom he falsely accused of stuffing ballot boxes in the 2020 contest.
  • More damages could be awarded against him in a sexual assault case brought by his former assistant Noelle Dunphy, who accuses him of demanding sexual favours including while he was on the phone to the White House. 

The background. Giuliani has already submitted to six hours of questioning in the Georgia case, brought by Fani Willis, district attorney for Fulton County in Atlanta. In a separate federal case brought by special prosecutor Jack Smith, in which Giuliani is an unnamed co-conspirator, he has attended two days of “Queen for a day” talks in which both parties explore possible grounds for a plea deal. 

Rico to Rico. The Georgia case is based on US racketeering laws designed to help prosecutors bundle together apparently disparate crimes and suspects as long as they can demonstrate a conspiracy at the heart of them. No one knows how Rico laws work better than Giuliani, who used them to bring down four New York mob families in one case in the Mafia Commission trial of 1985-86, which made his name. 

Is Rudy ready? He’s said he has “very good insurance” should he face jail time for his work for Trump. Ken Frydman, who worked on his first successful campaign for the New York mayoralty, says he’ll need to use it. 

“We can assume given his background in law enforcement and his relationships in that community… that he probably has some confidential information or photographs or videos of Donald Trump that he doesn’t want to be released,” Frydman tells Tortoise. “That’s what he means by insurance… He’s not going to jail for Donald Trump.”


Enjoyed this article?

Sign up to the Daily Sensemaker Newsletter

A free newsletter from Tortoise. Take once a day for greater clarity.



Tortoise logo

A free newsletter from Tortoise. Take once a day for greater clarity.



Tortoise logo

Download the Tortoise App

Download the free Tortoise app to read the Daily Sensemaker and listen to all our audio stories and investigations in high-fidelity.

App Store Google Play Store

Follow:


Copyright © 2026 Tortoise Media

All Rights Reserved