Giuliani's financial woes could compound as he faces mounting legal exposure

In 2007, when Rudy Giuliani launched his presidential bid, he seemed both politically and financially at the height of his powers.

His image as "America's mayor" in the wake of the 9/11 terror attacks made him an immediate contender for the Republican presidential nomination. And in the half-decade since he left New York's City Hall, lucrative consulting work and speaking fees had boosted his net worth to between $18 and $70 million, according to financial disclosures he filed at the time.

But Giuliani's presidential ambitions fizzled almost immediately, and the former New York City mayor failed to make it through Super Tuesday. It was a humbling political tumble -- and now, some 15 years later, his wallet appears to have taken an equally humbling hit.

A deluge of civil and criminal lawsuits has left Giuliani experiencing what his attorney called "financial difficulties."

The twin threats of potential legal exposure and an apparent depletion of resources could continue to compound in the months and perhaps years ahead, as the onetime attorney to former President Donald Trump battles the fallout from his activities in the wake of the 2020 presidential election.

Next week, a Washington, D.C.-based jury will determine what penalties Giuliani will owe a pair of Georgia election workers he was found to have defamed. He is already on the hook for some $230,000, and the election workers are seeking between $15 million and $43 million at trial.

Giuliani stands to owe millions more if he loses cases brought by two voting machine companies and his own longtime personal attorney, and he faces an unrelated sexual harassment suit for $10 million from a former business associate. In October, President Joe Biden's son Hunter Biden also sued Giuliani for unspecified damages, accusing him of mishandling personal data belonging to him.

Giuliani has denied all claims, and "unequivocally denies the allegations" in the sexual harassment suit.

But perhaps more concerning for Giuliani is the criminal racketeering indictment Fulton County District Attorney Fani Willis returned in August against him and 18 other co-defendants, including Trump, accusing them of unlawfully seeking to overturn the results of the 2020 presidential election in the state of Georgia. Giuliani -- who, like many of the other defendants, faces potential jail time in the case -- has pleaded not guilty to the charges.

Even if Giuliani emerges victorious from his legal tribulations, fighting them will undoubtedly rack up an immense cost.

"He has made it pretty clear that he doesn't have the resources to handle litigation," said one source familiar with Giuliani's legal situation.

To help raise money, Giuliani has turned to a deep-pocketed former client -- Trump himself. The former president reportedly recently hosted a $100,000-a-plate dinner at his Bedminster, New Jersey, estate, with proceeds going to Giuliani.

It was not immediately clear how much money the event raised -- though Giuliani's son has suggested it eclipsed $1 million -- or how much of those funds have made it to Giuliani. But one thing is clear, according to Giuliani himself: He needs the help.

Election lies -- and costs

In court filings over the summer, Giuliani's lawyer wrote a federal judge asking to defer payments Giuliani was ordered to pay to Ruby Freeman and Shaye Moss, two former election workers, citing "financial difficulties" as a result of fighting a slew of litigation elsewhere.

"Giuliani needs more time to pay the attorneys' fees," an attorney for Giuliani wrote.

Since then, the judge in that case has issued a summary judgment finding Giuliani liable for defamatory remarks he made about the two women during the Georgia presidential election recount. In a December 2020 appearance before a committee of the Georgia state legislature, Giuliani told lawmakers that a video circulating online showed "Ruby Freeman and Shaye Freeman Moss ... quite obviously surreptitiously passing around USB ports, as if they're vials of heroin or cocaine."

The judge initially ordered Giuliani to pay roughly $132,000 to cover Freeman and Moss' attorneys' fees -- but after Giuliani missed a deadline to submit payment earlier this month, the judge tacked on an additional $104,000. The judge ordered Giuliani to appear in person at a trial beginning next week to determine additional damages.

Beyond what Giuliani already owes in that lawsuit, he could lose even more substantial sums in his other suits.

In early 2021, voting machine company Dominion Voting Systems filed a string of lawsuits after Giuliani and others targeted the firm with false accusations that it orchestrated a plot to overturn the results of the 2020 election. Dominion's $1.3 billion lawsuit against Giuliani accuses him of carrying out "defamatory falsehoods" about Dominion, in part to enrich himself through legal fees and his podcast.

Dominion has since won an historic $787 million settlement against Fox News after filing a similar lawsuit against the conservative media giant seeking $1.6 billion dollars. The suit was settled just minutes before opening statements were set to begin in the trial.

Days after the Dominion suit was filed, Smartmatic, a voting technology company, followed suit, claiming that Giuliani, Fox News, and others "engaged in a widespread disinformation campaign" about the company's voting software rigging the election around the country.

Smartmatic is seeking a total of $2.7 billion in damages from Giuliani and the other defendants. Giuliani and other defendants have denied wrongdoing.

Paying his own attorneys

In September, Giuliani faced another potential legal blow from an unlikely source: his own longtime attorney and personal friend, Bob Costello.

Costello and his partners at Davidoff Butcher & Citron LLP accused Giuliani of owing them nearly $1.4 million for work defending him during numerous criminal, civil and congressional investigations. Giuliani has paid $214,000 to the firm since November 2019, when he retained Costello, the lawsuit said.

Costello represented Giuliani during criminal investigations in New York, Georgia and Washington and in 10 civil lawsuits in various state and federal courts, as well as during the House select committee's Jan. 6 investigation, and in disciplinary proceedings involving Giuliani's law license.

Giuliani has denied Costello's claim, but the allegation leveled by Costello is not the first of its kind.

In May, Bruce Castor, a former Trump impeachment attorney who agreed to defend Giuliani in a 2020 election-related civil suit, accused the former New York mayor of bilking him out of his attorneys' fees.

In court papers seeking to withdraw from the case, Castor, who said he had known Giuliani for decades, unloaded on Giuliani for his failure to cooperate with court-ordered documents on time -- telling the court that Giuliani "failed to provide the retainer sum" or "work even in the slightest with [Castor] to advance this case."

"That he promised to send the money and then didn't was a shock to me, and not in keeping with the character of the man I thought I knew when we were both prosecutors and later watching him from afar as mayor," Castor told ABC News. "Something had change in him."

A spokesperson for Giuliani rejected the claims at the time, insisting that Giuliani had indeed paid Castor for his work.

In the Fulton County racketeering case, two attorneys who initially represented Giuliani have since withdrawn, without public explanation.

One of those attorneys, David Wolfe, had previously defended Giuliani's payment record.

"Of course I'm getting paid for my work," Wolfe said in an interview on CNN over the summer. "I'm doing my work, I've been paid to do my work, and it's going to cause some problems for the state to respond to it."

But a source familiar with the matter told ABC News at the time that it remained unclear how long Wolfe would remain on the case. Wolfe resigned weeks later.

In the bank

Despite his entreaties for help and his self-described "financial difficulties," Giuliani's actual financial picture remains opaque, and at times has seemed to contradict his declarations of poverty in court.

Giuliani earns some $400,000 annually from advertisers on his daily WABC radio program, according to the New York Times, and in August, he traveled by private jet from New Jersey's Teterboro Airport to his initial court appearance in Georgia to face the racketeering charges. The longtime New York resident also recently listed his Upper East Side apartment for more than $6.5 million, according to Insider.

Ted Goodman, a political adviser to Giuliani, told ABC News that Giuliani's livestream show, "America's Mayor Live," brings in over five figures per month from advertisers.

The U.S. district judge overseeing Freeman and Moss' defamation case, Beryl Howell, recently cited Giuliani's luxury apartment and private flight in court documents, framing them as evidence that Giuliani's request to defer payments to the election workers was "dubious."

"In short, based on the current record, Giuliani has failed to show that he cannot pay the reimbursement fees he owes," Howell wrote.

Judge Howell had ordered Giuliani to share detailed financial information with attorneys for Freeman and Moss ahead of their upcoming trial to determine damages owed. Giuliani was supposed to submit details about his "assets and net worth," including "savings accounts, money market funds, mutual fund accounts, hedge fund accounts and certificates of deposit ... and financial statements."

Giuliani missed the Sept. 20 deadline to share all the information the judge requested; attorneys for Freeman and Moss said Giuliani only turned over a 2018 tax return and his divorce settlement from the same year. Judge Howell will instruct the jury to consider their request for additional sanctions against Giuliani at trial.

"It would be difficult to find a clearer example of an informed, sophisticated, and well represented party openly flouting orders of a federal court," attorneys for Freeman and Moss wrote in a recent filing in the case.

"Accordingly," they wrote, "severe sanctions are both warranted and necessary."

"The Rudy Giuliani you see today is the same man who took down the Mafia, cleaned up New York City and comforted the nation following September 11th," Goodman said in a statement to ABC News. "I implore folks to take the life of public service and accomplishments of Rudy Giuliani, and name a more consequential mayor or U.S. attorney in our nation's history."