Rudy Giuliani glared across a Washington hearing room as a lawyer seeking his disbarment after the Jan. 6 insurrection asked: How did this man, celebrated as “America’s mayor” after 9/11, become a leader of an attempt to overturn a national election?
“It’s like there are two different people,” Hamilton “Phil” Fox III, the lead prosecuting attorney for the agency that disciplines Washington lawyers, said last December. “I don’t know if something happened to Mr. Giuliani or what.”
Giuliani — feted, knighted and named Time magazine’s person of the year for his leadership as New York City mayor after the 2001 terrorist attack — has seen his reputation eviscerated and now his liberty imperiled for his steadfast defense of former President Donald Trump’s false claims about the 2020 election.
On Monday, Giuliani’s downfall sank to its lowest level yet with his indictment in Georgia on charges he acted as Trump’s chief co-conspirator in a plot to subvert President Joe Biden’s victory.
Giuliani, Trump and 17 other people were charged under Georgia’s version of the Racketeer Influenced and Corrupt Organizations Act. The law, known as RICO, was once one of Giuliani’s favorite tools when he was cracking down on mobsters and Wall Street titans as Manhattan’s top federal prosecutor in the 1980s. Now, as he nears 80, it could put him behind bars.
Giuliani called the indictment “an affront to American democracy” and said it “does permanent, irrevocable harm to our justice system.” On his radio show Wednesday, he described the case as an “atrocity” and an “out and out assault on the First Amendment.”
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 front runner 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.
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 last year. “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 U.S. 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 Sept. 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.
After his efforts to keep Trump in office failed in the courts, Giuliani on Jan. 6, 2021, made incendiary remarks to Trump supporters who later stormed the U.S. Capitol, suggesting they engage in “trial by combat.”
The New York State Bar Association said his words were intended to encourage Trump supporters “to take matters into their own hands.” A panel of the D.C. Bar Association unanimously recommended that he be disbarred, saying his misconduct “sadly transcends all his past accomplishments.”
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% of his mayoralty,” which ran from 1994 to 2001.
In the Georgia case, Giuliani is accused of making false statements, soliciting false testimony and seeking the illegal appointment of pro-Trump Electoral College voters. Giuliani was also described as a co-conspirator but not charged in special counsel Jack Smith’s election interference case against Trump.
Giuliani maintains that he had every right to raise questions about what he believed to be election fraud.
Today, he remains popular among conservatives in his hometown. He hosts a daily radio show in New York City and a nightly streaming show watched by a few hundred people on social media, which he calls America’s Mayor Live.
After 9/11, Giuliani started a consulting firm that had $100 million 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, he put his Manhattan apartment up for sale for $6.5 million.
Last year, 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.
In May, a woman who says she worked for Giuliani sued him, alleging he owed her nearly $2 million in unpaid wages and that he had coerced her into sex. Giuliani denied the allegations.
“His legacy is in tatters,” said Kirtzman, who was with Giuliani on 9/11 as they fled debris from the falling World Trade Center. He’s “gone through all of his money,” is facing prison and “will never change his feeling that he was right and everyone else was wrong.”
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