Rudolph W. Giuliani is running out of money and looking to collect from a longtime client who has yet to pay: former President Donald J. Trump.
To recover the millions of dollars he believes he is owed for his efforts to keep Mr. Trump in power, Mr. Giuliani first deferred to his lawyer, who pressed anyone in Mr. Trump’s circle who would listen.
When that fizzled out, Mr. Giuliani and his lawyer made personal appeals to the former president over a two-hour dinner in April at his Mar-a-Lago estate and in a private meeting at his golf club in West Palm Beach.
When those entreaties largely failed as well, Mr. Giuliani’s son, Andrew, who has an independent relationship with the former president, visited Mr. Trump at his club in New Jersey this month, with what people briefed on the meeting said was the hope of getting his father’s huge legal bills covered.
That appeared to help. Mr. Giuliani’s son asked that Mr. Trump attend two fund-raisers for the legal bills, and the former president agreed to do so, the people said.
Still, for the better part of a year, as Mr. Giuliani has racked up the bills battling an array of criminal investigations, private lawsuits and legal disciplinary proceedings stemming from his bid to keep Mr. Trump in office after the 2020 election, his team has repeatedly sought a lifeline from the former president, according to several people close to him. And even as the bills have pushed Mr. Giuliani close to a financial breaking point, the former president has largely demurred, the people said, despite making a vague promise during their dinner at Mar-a-Lago to pay up.
Mr. Giuliani, 79, who was criminally charged alongside Mr. Trump this week in the election conspiracy case in Georgia, is currently sitting on what one person familiar with his financial situation says is nearly $3 million in legal expenses. And that is before accounting for any money that Mr. Giuliani, the former mayor of New York City, might be owed for his work conducted after Election Day on Mr. Trump’s behalf.
Mr. Trump’s political action committee, which has doled out roughly $21 million on legal fees primarily for Mr. Trump but also for a number of people connected to investigations into him, has so far covered only $340,000 for Mr. Giuliani, a payment made in late May.
A spokesman for Mr. Trump did not respond to a request for comment, nor did a spokesman for Mr. Giuliani.
Mr. Giuliani, whose law license has been suspended because of his work to overturn the election, has few sources of income left, according to people close to him.
He earns roughly $400,000 a year from his WABC radio show, according to a person familiar with the matter. He also gets some income from a podcast he hosts, and, according to another person familiar, a livestream broadcast. The three cash streams are nowhere near enough to cover his debts, people close to him say. A legal-defense fund set up by friends to raise $5 million for him in 2021 took down its website after raising less than $10,000.
In the past, Mr. Trump has entered dangerous territory by not paying an associate’s legal bills when the case is connected to him, most notably with his former lawyer and fixer, Michael D. Cohen, who has become a chief antagonist and star witness against him. But people close to both Mr. Trump and Mr. Giuliani take it as an article of faith that the former mayor would never cooperate with investigators in any meaningful way against the former president. (Mr. Giuliani has said both he and his former client did nothing wrong.)
Among those who remain close to Mr. Giuliani, there is bafflement, concern and frustration that the former mayor, who encouraged Mr. Trump to declare victory on election night before all the votes were counted, has received little financial help.
Bernard B. Kerik, the former New York City police commissioner under Mr. Giuliani, who worked with the former mayor trying to identify evidence of fraud and who remains a supporter of Mr. Trump, puts the fault on people around the former president. Mr. Kerik was pardoned by Mr. Trump after pleading guilty to tax fraud and having lied to White House officials when President George W. Bush nominated him to be secretary of the Homeland Security Department.
“I know the president is surrounded by a number of people that despised Giuliani even before the election, more so after the election, for his loyalty to the president and for their relationship,” Mr. Kerik said. “It’s always been a point of contention for a number of people who I personally think didn’t serve the president well in the first place.”
Mr. Kerik added, “Where is everybody? Where’s the campaign?”
But, even as Mr. Kerik and others have blamed Mr. Trump’s inner circle for the lack of payments, the decision, as several people familiar with the matter noted, was always the former president’s.
Mr. Trump has never explicitly told Mr. Giuliani why he is effectively stiffing him, but the former president has pointed out that he lost the cases related to the election. That has been consistent with what Mr. Trump told aides shortly after Election Day, when an associate of Mr. Giuliani’s, Maria Ryan, asked the campaign in an email for $20,000 a day to pay for the former mayor’s work.
People close to the former mayor argue he was not working strictly on lawsuits, but also on research and efforts to keep state legislatures from certifying results Mr. Giuliani insisted were false. But Mr. Trump told aides he didn’t want Mr. Giuliani to receive “a dime” unless he succeeded. Some of Mr. Giuliani’s expenses were eventually paid, but only after Mr. Trump personally approved the money.
The effort to collect legal fees from Mr. Trump began in earnest more than two years ago. Mr. Giuliani’s main lawyer, Robert J. Costello, started calling people in Mr. Trump’s orbit, making the case that the former president was on the hook for legal fees Mr. Giuliani incurred because of his work for Mr. Trump. Mr. Costello has contacted at least six lawyers close to Mr. Trump, according to people with knowledge of the discussions, and most appeared sympathetic to Mr. Giuliani’s situation.
This spring, Mr. Giuliani reached out to Mr. Trump directly and asked to meet, the people said. Mr. Trump agreed, and in late April, they met at Mr. Trump’s golf club in West Palm Beach.
The meeting was pleasant, and lasted more than an hour, a person familiar with the meeting said. But Mr. Trump, who was accompanied by one of his Florida attorneys, was noncommittal.
Yet he agreed to meet them again, two days later, at his private club, Mar-a-Lago, a meeting previously reported by CNN. Over a nearly two-hour dinner, Mr. Costello pressed Mr. Trump to cover not only Mr. Giuliani’s legal bills, but also to pay him for the work Mr. Giuliani provided Mr. Trump in the wake of the 2020 election.
Mr. Trump resisted, noting that Mr. Giuliani did not win any of those cases. Mr. Costello, who did most of the talking for Mr. Giuliani, said that the money was not coming out of Mr. Trump’s own pocket, but rather the coffers of his PAC. By the end of the dinner, Mr. Trump agreed that Mr. Giuliani would be paid, one person said. But in the weeks that followed, neither he nor the PAC delivered. And Mr. Giuliani was growing more and more desperate.
A federal judge was exasperated with Mr. Giuliani for failing to search for records as part of a defamation lawsuit that two Georgia election workers filed against him because he falsely accused them of stealing ballots. Mr. Giuliani said that he could not afford to pay for a vendor to do so.
Mr. Costello pleaded with Mr. Trump’s aides to pay off Mr. Giuliani’s balance with the vendor, and the PAC made a $340,000 payment to that firm.
Since then, however, the PAC has not covered any other bills for Mr. Giuliani.
It has been a remarkable reversal of fortune for Mr. Giuliani, who was once worth tens of millions of dollars made partly on contracts he signed after leaving City Hall in New York, having become known as “America’s mayor” for his performance in the aftermath of the Sept. 11, 2001, attacks.
A divorce from his third wife, Judith Nathan, cost him much of his wealth around the time he left his law firm to represent Mr. Trump, then the president, in the investigation brought by the special counsel Robert S. Mueller III over whether the Trump campaign conspired with Russian officials in the 2016 election.
From there, Mr. Giuliani engaged in campaign efforts to find damaging information about Joseph R. Biden Jr. in Ukraine, where Mr. Biden’s son had business dealings, efforts that helped lead to Mr. Trump’s first impeachment.