Rudy hits rock-bottom: Giuliani, once revered prosecutor who took on the mob, is disbarred in his New York hometown

After a storied career in law and politics spanning decades, the 80-year-old is facing legal and financial jeopardy

Rudy Giuliani, the revered prosecutor who took on the New York mafia and led the city through the 9/11 terror attacks, has been disbarred in his own hometown.

The decision, by a New York Appellate Court on Tuesday, was a stunning conclusion for a man who was once one of the most powerful prosecutors in the country.

As US Attorney for the Southern District of New York, Giuliani became known as a tough prosecutor who went after organized crime. It was a reputation he leveraged to become New York mayor, leading the city through the devastation of the 9/11 terror attack in 2001.

On Tuesday, the NY appellate court cited the former mayor’s repeated false claims regarding the 2020 election as the reason for his disbarrment. As a lawyer for former president Donald Trump, Giuliani was one of the main mouthpieces for the baseless and fact-free argument that the election had been stolen.

The 80-year-old is in both legal and financial hot water.

New York Mayor Rudy Giuliani leads a tour of the site of the World Trade Center terror attack on September 12, 2001. On 2 July, 2024, he was disbarred in New York (2001 AP)

Giuliani filed for bankruptcy in December after a defamation judgment that ordered him to pay $148m in damages to two election workers about whom he made false claims. He was indicted in May, along with 17 others, in Arizona for supposedly being a part of a scheme to overturn Trump’s 2020 loss in the state. Giuliani faces a similar indictment in Georgia.

He is also under scrutiny in connection with other proceedings in New York. He faces a $10m complaint from a former staffer who has accused him of sexual assault and wage theft. There are also claims that he was selling pardons for $2m, but many of the actions against him were stayed following his bankruptcy ruling. Giuliani has rejected the allegations.

A Washington DC disciplinary committee has recommended that he be disbarred there as well.

Giuliani — feted, knighted, and named Time magazine’s Person of the Year for his leadership as New York City mayor after the 2001 terrorist attacks — has seen his reputation eviscerated and now his liberty imperiled for his steadfast defense of Trump.

How did it come to this? People who’ve studied Giuliani’s rise and fall see his failed 2008 presidential run as a turning point.

Giuliani started as the frontrunner for the Republican nomination, capitalizing on his post-9/11 popularity. But he struggled in the primaries amid GOP concerns about his past support for abortion rights, gay rights, and gun control, and questions about his personal life and business ties to the Middle East.

Rudy Giuliani, here seen in 1984, served as a US attorney between 1983 and 1989. He rode his success as a prosecutor all the way to the New York mayoralty (Bernard Gotfryd/Alamy)

For years following the race, Giuliani's political career appeared over. After falling into a deep depression, he and his then-wife Judith decamped to Florida, where Trump put them up for a month in a bungalow at his Mar-a-Lago estate, biographer Andrew Kirtzman said.

“Trump really took Giuliani under his wing at a very vulnerable moment,” said Kirtzman, whose second Giuliani biography, Giuliani: The Rise and Tragic Fall of America’s Mayor, was published in September 2022. “And then in 2016, Trump decided to run for president, and he needed Giuliani, and Giuliani needed Trump.”

Trump, a first-time candidate, leaned on Giuliani's political acumen and loyalty and put him to work as a surrogate leading attacks on former Secretary of State Hillary Clinton, whom Giuliani had faced in a 2000 Senate race.

The 2016 campaign returned Giuliani to relevance, but he surprised many with the ferocity of his attacks and his frequent claims that Clinton had committed crimes. Giuliani was seen as squandering his image as an elder statesman of sorts on a candidate who, at the time, was written off as having little chance to win.

Giuliani angled for a post in Trump's cabinet but didn't get it. Instead, he continued as Trump's attack dog, a role that saw him traveling to Ukraine seeking damaging information about Biden's son, Hunter.

Giuliani's contacts with Ukrainian figures later played a role in Trump’s first impeachment trial and prompted an FBI investigation. In April 2021, federal agents raided his home and office, seizing computers and cellphones, but the probe was later dropped without any charges.

Some people who were once close to him say the Giuliani of today has little in common with the man they knew.

“The man that I knew 20 years ago, the hero of September 11 bears no resemblance to this man,” said Judith Giuliani, who was by his side in the aftermath of 9/11 and his 2008 election loss. “I actually feel sorry for him. It’s sad. He’s not the person that he used to be to any of us.”

When Trump lost the 2020 election, Giuliani played a starring role in his effort to remain in the White House, which prosecutors say included illegal maneuvering to flip the results in key states.

He was ridiculed for holding a news conference on Pennsylvania legal challenges outside Four Seasons Total Landscaping in Philadelphia, an out-of-the-way location next to a crematorium and a pornography shop, not the Four Seasons hotel in the heart of the city.

A few weeks later, Giuliani appeared to have hair dye streaking down his face at another news conference, making him the butt of late-night television jokes and internet memes.

Those blunders came in the wake of another embarrassment: clips from the “Borat” sequel showing Giuliani flirting with a young actress posing as a TV journalist and then lying on a bed, with his hand down his pants. Giuliani said he went to the hotel thinking he was going to be interviewed and was just tucking in his shirt.

Former New York Mayor Rudy Giuliani departs the U.S. District Courthouse in Washington on December 15, 2023. He was ordered to pay $148m in damages to two election workers (REUTERS)

After his efforts to keep Trump in office failed in the courts, Giuliani on January 6, 2021, made incendiary remarks to Trump supporters who later stormed the U.S. Capitol, suggesting they engage in “trial by combat.”

Giuliani’s critics argue that he’s always been combative and abrasive, with a disdain for critics and a willingness to go after rivals.

“The real Rudy Giuliani was hiding in plain sight,” said Donna Lieberman, executive director of the New York Civil Liberties Union.

“Just because he was the face of a devastated and pained city after 9/11 doesn’t mean that he wasn’t still the authoritarian, anti-democratic bully” that he was “for 90 percent of his mayoralty,” which ran from 1994 to 2001.

After 9/11, Giuliani started a consulting firm that had $100m in revenue in five years. Lately, though, he's shown signs of financial strain, exacerbated by a third divorce, costly lawsuits, and investigations.

To generate cash, he’s hawked autographed 9/11 shirts for $911 dollars and pitched sandals sold by election denier Mike Lindell. He’s also joined Cameo, a service where celebrities record short videos for profit. Giuliani’s greetings cost $325 a pop.

In July last year, he put his Manhattan apartment up for sale for $6.5m before taking it off the market.

In 2022, a judge threatened Giuliani with jail in a dispute over money owed to Judith, his third ex-wife. Giuliani said he was making progress paying the debt, which she said totaled more than $260,000.

“His legacy is in tatters,” said Kirtzman, who was with Giuliani on 9/11 as they fled debris from the falling World Trade Center.