Rudy Giuliani, the former New York mayor and onetime attorney to Donald Trump, owes millions of dollars in legal fees, a source familiar with the matter told CNN, a debt that Giuliani hopes to eat into Thursday night at a fundraiser at Trump's Bedminster golf club.
Amid a host of lawsuits and now criminal charges tied to his efforts to overturn the 2020 election, Giuliani is expected to take in more than $1 million for his legal defense fund at a $100,000-a-plate fundraiser hosted by Trump Thursday evening. It is the first of two fundraisers Trump is expected to sponsor for Giuliani.
Giuliani's son, Andrew Giuliani, who helped organize the fundraiser at Trump's New Jersey club, said in an interview Thursday on Sid Rosenberg's WABC radio show that the event would not cover all of Giuliani's legal fees. But he said that it would help Giuliani "be able to have the resources necessary to put a team together to fight against what many of us see as political prosecutions."
Giuliani's closest allies have been soliciting donations from people the former New York mayor has helped in the past -- including former deputies and politicians who previously solicited favors from Giuliani, as well as from high-dollar donors who have contributed to Giuliani's political endeavors. It's unclear how successful this effort has been, but a source familiar with the legal defense fund said it has raised "peanuts" compared to the millions of dollars Giuliani owes.
The fundraiser at Bedminster comes amid a split in Trump world about whether the former president should be doing more to help Giuliani pay for his mounting legal bills, multiple sources familiar with the conversations and dynamics between the two men told CNN.
Trump has pushed back on the idea that he should pay Giuliani's bills himself so that their interests remain aligned, arguing that he hasn't committed any wrongdoing, some sources said.
But despite not paying his legal bills, the two men still spend time together. Trump and Giuliani ate lunch together Monday and greeted Trump supporters together at the former president's Bedminster resort.
Giuliani has struggled to pay his legal bills -- which one source estimated to be as high as $5 million -- while defending against multiple defamation lawsuits. Giuliani has been sued over his comments and actions after the 2020 election spreading false claims of election fraud.
Last week, a judge ruled Giuliani lost a defamation lawsuit from two Georgia election workers against him after he failed to provide information sought in subpoenas. He has already been sanctioned nearly $90,000 in attorneys' fees and now faces the prospect of significant damages that could amount to thousands if not millions of dollars.
And in a defamation case brought by voting technology company Smartmatic against Giuliani and others, his attorney said last month that Giuliani couldn't afford to pay $15,000 to a data-hosting company for an electronic search of his phone records.
Giuliani is also facing criminal charges in Fulton County, Georgia, for his role in an alleged conspiracy to subvert the will of voters after Trump lost the state to Joe Biden in 2020.
Legal bills for the Fulton County case could easily add millions to Giuliani's tab. Prosecutors told Judge Scott McAfee Wednesday that they expect the Georgia trial will last approximately four months and they intend to call more than 150 witnesses. Giuliani is currently represented in the Georgia case by attorneys Brian Tevis and David Wolfe, as well as New York based attorney John Esposito.
But it is still unclear if Giuliani will be able to come up with the money to retain his defense team.
'Some of those people don't like Rudy Giuliani'
There is disagreement among Trump advisors about whether he should be helping Giuliani. Multiple advisers have told Trump that it would be in his best interest to help his former lawyer with these bills as a way to keep him in the fold and to aid a longtime ally.
Others have encouraged the former president to cut Giuliani loose.
Andrew Giuliani blamed some Trump aides for suggesting there was a wedge between them. During his WABC interview, he said that his father was willing to tell Trump when he "sees somebody that's yessing him to death" who isn't giving the former president good information.
"And guess what -- some of those people don't like Rudy Giuliani for doing that," Andrew Giuliani said.
Sources close to Trump pushed back on the idea that Trump was not helping Giuliani, specifically pointing to the fundraisers he has agreed to sponsor, as well as a payment from his political action committee to cover Giuliani's debt to a data-hosting company.
"This is his way of helping him," one source said.
Trump has paid the full legal bills of a number of advisers, aides and employees connected to both the House select committee that investigated January 6, 2021, and the federal investigations into the former president.
Many of these individual whose bills Trump's PAC has covered are relatively unknown, unlike Giuliani, who still has supporters willing to dole out money at fundraisers.
Bernie Kerik, Giuliani's longtime friend and former New York police commissioner, is advising him on finding lawyers and also raising money to help pay Giuliani's outstanding bills, according to sources. Kerik traveled with Giuliani to Georgia for his arraignment last month and was seen walking with the former mayor into the Fulton County jail.
"I don't care who you are and what you have done for Trump -- Giuliani's done ten-times more and suffered more than anyone," Kerik told CNN. He estimates Giuliani has lost between $10-$20 million in business because of his work for Trump.
Kerik worked closely with Giuliani after the 2020 election to chase down supposed election fraud. Though he is not charged in the sprawling indictment out of Fulton County, Kerik's attorney confirmed to CNN that Kerik is the unnamed individual listed in the indictment as co-conspirator 5.
Giuliani won't ask for money himself
Giuliani currently owes more than $1 million to his former attorney Robert Costello, according to a source familiar with matter. As CNN first reported, the two men met with Trump earlier this year to discuss helping pay off Giuliani's legal debt. But multiple sources said Costello did all the talking in those meetings.
Giuliani has not been willing to personally ask Trump for help directly.
"He will not do it. He thinks its disrespectful to the president," a source close to Giuliani said.
After the meetings with Costello, Trump's Save America political action committee paid $340,000 to a data-hosting company, Trustpoint, on Giuliani's behalf, according to federal campaign records. CNN confirmed that the payment from Trump's leadership PAC -- which has paid roughly $40 million in legal fees for Trump and his aides and advisers -- covered Giuliani's debt with the company and allowed him to pay for an additional search for evidence.
Trump also agreed after meeting with Giuliani and Costello to attend two fundraisers for Giuliani, a source said.
Andrew Giuliani has also made direct appeals to Trump on behalf of his father. The younger Giuliani, who set up a political action committee to help with his father's legal bills, has developed his own relationship with Trump.
'They love the chaos'
Sources who have spent time with Trump and Rudy Giuliani describe a friendship and said that the former president remains very fond of the former mayor.
"It's not that he is refusing to help," one source said, noting Trump's PAC's payment for Giuliani's debt to the data-hosting company. The source also said Trump had not ruled out taking on more of Giuliani's legal bills in the future, should his other fundraising efforts fall short.
Andrew Giuliani, who did not respond to CNN's questions about Thursday's fundraiser, said on WABC Thursday that the former New York mayor is ready to take on the charges against him.
When he called his father to ask how he was feeling shortly after the Fulton County indictment was unveiled, Andrew Giuliani said he was "almost chipper because he had a challenge."
"I hang up the phone and I'm like, 'This guy's half-crazy. He loves the chaos,'" the younger Giuliani said. "He's like Trump in that in that regard. And that really is true. They're wired a little bit differently than most of us. They love the chaos. They love the challenge."