There was a time when former New York mayor Rudy Giuliani wouldn’t have been able to pay for his own drink in a bar. In the aftermath of the September 11, 2001, terrorist attacks that took down both towers of the World Trade Center in New York City, Giuliani became known as “America’s Mayor” while leading the recovery process. His popularity soared, and he even made a run at becoming the Republican candidate for president in 2008 before bowing out after a weak showing in the primary. A former U.S. Attorney for the Southern District of New York, he first made his name prosecuting organized crime bosses and other criminals.
Things haven’t gone quite so well for Giuliani since then, as evidenced by a decision handed down on September 16, 2025, in his former Manhattan stomping grounds. New York State Judge Arthur Engoron ruled that Rudy Giuliani must pay over $1.3 million in unpaid legal fees to the law firm that represented him in numerous cases between 2019 and 2023. These include lawsuits for false claims made about alleged election fraud during the 2020 elections. Giuliani had argued that his retainer contract was with one of the partners and not with the firm, and that he had never agreed to the hourly rate.
Justice Engoron didn’t buy Giuliani’s defense, causing an attorney for the former mayor to announce they would be taking the case to the appellate court. One hopes they got their fees paid up front.
America’s Mayor
Before he became the New York City mayor, Giuliani was well on his way to becoming a household name through his career in the U.S. Department of Justice, working in the Southern District of New York. In addition to convicting three heads of the infamous New York mafia Five Families (another was assassinated on the streets while under indictment), Giuliani took down Wall Street moguls Ivan Boesky and Michael Milken. The latter cut a deal after being indicted on 98 counts of racketeering and fraud.
Running as a Republican, the former Democrat and Independent lost his first mayoral campaign to David Dinkins in 1989. He defeated Dinkins in 1993, although some called his campaign’s hiring of off-duty police, corrections officers, and firemen to “monitor voting fraud” at polling stations blatant voter intimidation. Giuliani won again in 1997 and, facing a term limit, mounted a run for Senate. His campaign collapsed amid a prostate cancer diagnosis, the revealing of his extramarital affair, and his separation from his wife.
Giuliani was the mayor when planes struck and collapsed the towers of the World Trade Center. His determination and leadership over the ensuing months cast him as a hero in the eyes of many across the nation and saw him named Time Magazine’s Person of the Year for 2001. In high demand for speaking appearances, he tried to parlay his popularity into a presidential bid in 2008. After that failed, he became a political consultant before becoming a vocal supporter of Donald Trump in 2015.
From Rubble To Ruin
Although he was rumored for several Cabinet positions during President Donald Trump’s first term, Giuliani instead served as one of his personal lawyers. He often acted as a public figure during the Mueller investigation and the payoff scandal involving adult film actress Stormy Daniels.
After President Trump lost the 2020 presidential election to President Joseph Biden, Giuliani became the leader of the “elite strike force” tasked with exposing alleged voting fraud by the White House. Giuliani and the others' wild accusations resulted in 63 losses in court, with most cases dismissed when the accusers were unable to provide any kind of evidence. Further lowlights included Giuliani holding a press conference outside a landscaping company with the same name as a prestigious hotel, and hair dye running down his face as he sweated heavily during another appearance.
Giuliani’s woes continued to mount as those he’d accused of voting fraud fired their own legal salvos in his direction. Two Georgia election workers in Fulton County, who suffered threats on their lives after Giuliani’s baseless accusations, won a defamation case against him in 2023. Giuliani’s attempt to declare bankruptcy to avoid payment was denied, and he settled with the plaintiffs for an undisclosed amount.
The former mayor has maintained that President Trump’s campaign owes him over $2 million in legal fees. In 2021, Trump said, “I do pay my lawyers when they do a good job.” It’s uncertain if he was specifically referring to Giuliani and his failures in challenging the election results.
Do They Offer a Payment Plan?
The law firm of Davidoff Hutcher & Citron, along with former partner Robert Costello, claims that Giuliani has paid less than 15% of his outstanding legal bill and owes them $1.36 million. The court order from Justice Engoron instructs Giuliani to pay his legal fees with interest. Appeals court is next, but what appeals to be a clear-cut case of outstanding debt might not be easily reversed. He’s also still embroiled in lawsuits filed by voting machine companies that have won hefty settlements from others to avoid a defamation judgment.
As for bars, some are less friendly to Giuliani than others. The New York Bar Association revoked his license to practice law due to making false and misleading statements in court during the election cases in 2024. The District of Columbia followed suit and disbarred him as well later that year. If he chooses to ignore the judge’s order, Giuliani will likely add a contempt of court charge to his headaches.
Related Resources
- Attorneys and Fees (FindLaw’s Filing a Lawsuit)
- What Does It Really Take To Get Disbarred? (FindLaw’s Greedy Associates)
- Court Can Consider Attorneys’ Ability To Pay Court Sanctions (FindLaw’s Practice of Law)
