Rudy Giuliani was down in the dumps.
It was January 2008, and the former New York City mayor had flamed out of the Republican presidential primaries in spectacular fashion.
He had longed to be the first Italian-American president of the United States. Now what?
“In the wake of that crash and burn, Giuliani started to drink and went into a depression,” said Andrew Kirtzman, a longtime New York City journalist who has written two biographies of Giuliani.
An unlikely figure stepped up to help: Donald Trump.
The real estate mogul allowed Giuliani and his third wife, Judith, to stay at a cottage at Mar-A-Lago where he was able to recuperate outside of the prying eyes of the media.
“It was Donald Trump who came to his rescue,” said Kirtzman, who recounted the episode in his 2022 book, “Giuliani: The Rise and Tragic Fall of America’s Mayor.”
Some 15 years later, Giuliani has been charged with engaging in a conspiracy to overturn the results of the 2020 presidential election on behalf of Trump.
The indictment handed down by a grand jury in Fulton County, Georgia, marks the most dramatic turn in the long relationship between the two quintessentially New York figures. For Giuliani the charges also represent a new low in the career arc of a man who was once one of the most admired people on the planet.
“His fall from grace is almost complete,” said Ken Frydman, who served as Giuliani’s press secretary during the 1993 mayoral campaign. “His only goal should be to die a free man.”
Giuliani enjoyed a meteoric rise in the 1980s and 1990s.
He was the Justice Department’s No. 3 official during the Reagan administration. He was the hard-charging head of the U.S. attorney’s office in Manhattan who dismantled the Mafia’s “five families.” He was “America’s Mayor,” whose calm, unwavering leadership steadied New York in the aftermath of 9/11.
But his escapades in more recent years have both stunned and saddened many of his former colleagues and aides. As Trump’s chief fixer and attack dog, Giuliani peddled conspiracy theories and pushed false allegations about the Biden family and the 2020 election, entangling him in both of Trump’s impeachments.
“His only goal should be to die a free man.”
— Ken Frydman, former Giuliani press secretary
He’s now being sued by two voting machine manufacturers over his election fraud claims, by a pair of Fulton County poll workers who allege that he defamed them, and by a woman who has accused him of “wide-ranging sexual assault.” (Giuliani has denied all of the allegations.)
“The current version of Rudy is not understandable to the people who thought they knew him when he was younger,” said John Flannery, a former federal prosecutor who worked with Giuliani in the mid-1970s.
Flannery said his discussions with old colleagues about Giuliani invariably turn to the famous 19th century Lord Acton quote — power tends to corrupt, and absolute power corrupts absolutely.
“He got close enough to taste it, and he just needs it,” Flannery said.
'A Greek tragedy'
The indictment accuses Giuliani and 18 others, including Trump, of violating Georgia’s Racketeering Influenced and Corrupt Organizations Act (RICO), which is modeled on a federal law Giuliani famously championed when he was busting up the mob in New York.
As part of the alleged criminal enterprise, Giuliani pressed election officials in Pennsylvania and Arizona to act on bogus claims of election fraud and oversaw news conferences that falsely alleged voting machines were rigged, prosecutors say.
He and Trump are both facing 13 counts, more than any other defendant.
Giuliani has maintained his innocence and attacked the case with characteristic bravado.
“This indictment is an affront to American Democracy and does permanent, irrevocable harm to our justice system,” he posted online after the charges were made public.
“It’s just the next chapter in a book of lies with the purpose of framing President Donald Trump and anyone willing to take on the ruling regime.”
Many of his former colleagues and friends have abandoned him, but he still has his defenders, which include a celebrity divorce attorney and, improbably, one of the former Mafia members he prosecuted.
Michael Franzese, an ex-Colombo family member who was known as the “Yuppie Don,” was indicted by Giuliani’s office for racketeering in 1984, but he was acquitted at trial.
“I had as much business being in that case as you did,” Franzese said in an interview.
Franzese ultimately served eight years in prison after he pleaded guilty in a racketeering case brought by Brooklyn federal prosecutors. While behind bars, he renounced his gangster ways and left the mob, becoming a motivational speaker and author.
Franzese said he was both shocked and grateful when Giuliani agreed last year to write the foreword to his book, "Mafia Democracy."
“My opinion of him has changed,” Franzese said. “I don’t want him to go to prison.”
Raoul Felder, a high-profile divorce lawyer, said he believes his longtime friend will beat the case.
“For Rudy, it’s a Greek tragedy because he’s a man of enormous talent, enormous temperament, enormous ethical principles,” Felder said.
Jeffrey Harris holds a much different view of Giuliani and the charges he now faces.
Harris and Giuliani were close friends when they worked together as assistant U.S. attorneys in New York in the 1970s and later at the Justice Department in Washington. But Harris said he can’t understand what became of the smart, outstanding lawyer he knew.
“When I was thinking about marrying my wife, the person I went to to see what he thought was Rudy,” Harris said. “This pains my heart.”
Among the most outrageous claims cited in the indictment were Giuliani’s allegations during a state legislative hearing in Georgia that two Black election workers, Ruby Freeman and her daughter, Shaye Moss, were “quite obviously surreptitiously passing around USB ports as if they’re vials of heroin or cocaine.” (Moss later testified that it was a “ginger mint.”)
Harris said he was reminded of an old story when he watched clips of Giuliani bad-mouthing Freeman and Moss.
It was around 1982. The two men had just returned to their desks at the Justice Department after running out to pick up lunch when Giuliani received a call from the Office of Professional Responsibility, saying someone had reported that he had walked through the building’s courtyard carrying a brown bag full of drugs.
“It was obviously BS, and he was apoplectic to say the least,” Harris said. “He could talk about nothing else for the rest of the day.”
“Here’s a guy who should know better,” Harris added, referring to Giuliani’s false claims about the election workers, “because when a similar thing happened to him the outrage was uncontained.”
Ted Goodman, Giuliani's political adviser, defended Giuliani's legacy and hit back at the ex-mayor's former colleagues-turned-critics.
“I get it," Goodman said in a statement. "It’s probably easier to say nasty things about the mayor in order to stay in good graces with New York’s so-called 'high society' social circles and the Washington D.C. cocktail circuit, but I would remind these 'former colleagues' that Rudy Giuliani is the most effective federal prosecutor in American history, he improved the quality of life for more people than any Mayor in American history, and he comforted the nation following September 11th.
“No one can take away his great accomplishments and contributions to the country."
'A fallen hero'
Giuliani has known Trump for decades.
In some ways, they were kindred spirits. Both were larger-than-life New York figures who craved attention and prized loyalty.
Giuliani delivered a eulogy at the funeral of Trump’s father, Fred, in 1999 and attended Trump’s wedding at Mar-a-Lago in 2005.
In 2000, the two men appeared together in a memorable skit for an annual charity dinner, with Giuliani dressed in drag and Trump nuzzling the then-mayor’s fake bosom.
“Oh, you dirty boy, you!” Giuliani exclaimed before slapping Trump in the face.
Their relationship had benefits for Trump that went beyond comedic cameos.
During Giuliani’s mayoralty, Trump pushed to build the world’s tallest residential building in the shadow of the United Nations headquarters on Manhattan’s East Side. A coalition of residents, including legendary newsman Walter Cronkite, fought the development and implored Giuliani to reject it.
But the mayor stood by Trump, and the building eventually went up.
Less than 10 years later, Giuliani’s failed bid for the GOP nomination ended when he came in a distant third in Florida, the state he had banked his candidacy on.
Giuliani focused on his consulting and security businesses and began to fade from public view.
But in 2016, he got his chance to regain the spotlight. Now it was Trump who was gunning for the Republican nomination for president. But who was going to back him?
“He had almost no political supporters,” said Kirtzman, the Giuliani biographer. “The guy he knew was Rudy Giuliani.”
Trump reached out to Giuliani, and over the ensuing years it would become clear that he found his most pugnacious advocate, a man who jumped at the chance to once again bask in the limelight.
“The truth is, no one else was making those calls to Giuliani at the time,” said Kirtzman. “He was a fallen hero.”
Giuliani announced his endorsement in an awkward TV interview in April 2016 as Trump was hurtling toward the nomination. Giuliani repeatedly emphasized that he was not part of Trump's campaign, but six months later, the former mayor stepped up for Trump when almost no one else would.
It was Giuliani who went on TV to defend Trump after the release of the "Access Hollywood" tape, a 2005 recording in which Trump had, seemingly unaware he was being recorded, talked about grabbing women.
There would be reporter butt dials, a hair dye mishap, an embarrassing movie cameo and an infamous news conference at a landscaping business next to a sex shop. But Giuliani has remained in Trump’s good graces.
Whether their relationship will survive criminal charges remains an open question.
Wayne Barrett, the renowned investigative reporter who died in 2017, summed up the man Giuliani had become in a blistering 2016 column for the New York Daily News.
“What is amazing after all these discrediting years,” Barrett wrote, “is that he is still treated as a voice of reason, even when he echoes, or inspires, Trump.
“It is, for both, the last gasp of rapacity, a final dance with grand destiny, propelled by howls of aging ambition.”
