Twenty-five years since his leadership in the wake of the 9/11 terrorist attacks garnered him universal praise and the moniker “America’s mayor,” a quarter-century of scandal and disgrace has clouded Rudy Giuliani’s peak in public life.
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Barred from practicing law, accused of plotting to overthrow democracy and rig an election for Donald Trump in two criminal indictments, a third divorce, and a humiliating cameo in a “Borat” film, the steady stream of controversies has yet to cease.
The swell of scandals has subsumed the 82-year-old Giuliani’s once-prestigious reputation as the hard-charging Manhattan U.S. attorney credited with taking down the mob before pulling New York City out of its “bad old days” after he became mayor in 1994, all but erasing the memory of his leadership in the wake of the deadliest attack on the U.S. in its history.
“He was the face of American pain,” recalled veteran political consultant Hank Sheinkopf.
“America had experienced Pearl Harbor 2, and the president wasn’t there, but he was there. There he was walking down the street, with white powder on his shoulders, with his police commissioner following him and a retinue of other people, and he was leading the country. He was America’s mayor at that moment, at a time when the country was at great risk, and no one knew what this meant.”
Today, the isolated former mayor lives in Florida, having sold his Upper East Side co-op last year for a fraction of the price he paid for it while tangled in a maze of legal debt.
Once the iconic images of him holding a respirator to his face as he emerged from the wreckage of the collapsed Twin Towers, the photographs that today define Giuliani’s life in politics show him falsely crying election fraud in the parking lot of a Philadelphia landscaping company with hair dye streaming from his scalp when President Joe Biden was declared the winner of the 2020 election.
“He will be remembered as the man with dye down his face, red dye falling from coloring his hair, who shilled for a very bad idea — that America’s electoral system was a fraud,” Sheinkopf said.
“That red dye replaced the white dust on his shoulders. He’s a tragic American figure, unquestionably so.”
Scandal in the leadup to 9/11
Easy to overlook in Giuliani’s story is that his reputation was in rough shape before the tragic events of 9/11.
Giuliani’s ascent to beloved national icon in the final months of his second term as mayor followed an otherwise tumultuous last year in office. Four months before the attacks, the Daily News reported that his personal dramas were losing him his edge in a special feature titled “Rudy’s Crumbling World.”
“Will Giuliani be remembered like his hero, Mayor Fiorello LaGuardia, as a hard-charging reformer who brought order and prosperity back to a city that seemed to lack both?” The News asked in May 2001. “Or will his political epitaph read more along the lines of Jimmy Walker, the charismatic Depression-era mayor who is remembered more for his comely mistress than for anything he did at City Hall?”
Amid a bout with prostate cancer and his divorce from Donna Hanover, City Hall insiders described the lame duck mayor as zoning out in briefings and increasingly leaving his deputies at the helm.
His personal life had become such a soap opera that, weeks before the attacks, he moved out of Gracie Mansion after the courts sided with Hanover, the mother of his children. He had unsuccessfully attempted to evict the city’s first lady to make room for his mistress, Judith Nathan, with whom he had an equally bitter divorce in 2018.
While many credit Giuliani with bringing down crime in the city during his first term, critics said his hardline tactics went too far and disproportionately harmed New Yorkers of color.
“The personal foibles, that was one thing, but his endless encouragement of police brutality, his constant defense of brutal cops and the worst parts of the criminal legal system, including mass incarceration, his highly personal attacks on the victims of police brutality comes to mind,” civil rights attorney Ron Kuby said.
“9/11 saved Rudy’s political career, his political life,” said Kuby, “until he threw it away again.”
Becoming ‘America’s Mayor’
After the attacks, Giuliani’s personal woes took a back seat as a grieving city looked for guidance.
As lower Manhattan disappeared behind a plume of darkness, debris and death on the morning of Sept. 11, 2001, and President George Bush circled the skies in Air Force 1, then-Mayor Giuliani was the leader who stepped up to address a horrified and heartbroken nation.
“The number of casualties will be more than any of us can bear, ultimately,” the visibly shaken mayor told reporters in the hours after the attacks.
Hailed for his heroism, eloquence and unifying words of comfort, Giuliani would be anointed within weeks by Oprah Winfrey as “America’s mayor,” appear for a cold open on Saturday Night Live, and be named TIME’s person of the year.
The high note Giuliani left office on — after mulling avenues to stay in office past the limitation — burnished his public profile with lucrative results, said his 1993 campaign secretary Ken Frydman.
“He was making hundreds of thousands of dollars for speeches after 9/11, and was killing it,” Frydman said.
Giuliani ran for the Republican nomination in the 2008 presidential election, entering the race in the lead but ultimately dropping out and endorsing Sen. John McCain when he came third in the Florida primary. McCain would go on to lose to President Barack Obama.
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His White House ambitions returned within a decade, in 2015, when he put his full-throated support behind Trump in what many consider Giuliani’s point of no return.
“He sold his soul to Donald Trump,” Frydman said.
The Trump years, legal troubles
A surrogate in Trump’s 2016 presidential campaign, Giuliani was vice chair of Trump’s transition and alternately served as the president’s cybersecurity czar and personal lawyer after Trump took office.
By 2019, he was under the microscope at the office he once led when prosecutors in the Southern District of New York began investigating him after the arrests of his business associates for a campaign finance scheme that overlapped with a pressure campaign on Ukrainian officials with Russia ties to dig up dirt on Biden.
The former mayor’s legal troubles reached new heights after he played a leading role in Trump’s efforts to cling to power after the 2020 election, calling for “trial by combat” at a rally preceding the insurrection on the Capitol on Jan. 6.
“In my mind, Giuliani is more culpable for January 6th than Trump because Trump was sitting with his feet up at the White House when they took the Capitol,” Frydman said.
Georgia prosecutors responded with criminal charges in August 2023, indicting Giuliani, Trump and more than a dozen others on the kind of RICO charges he helped pioneer in the 1980s, alleging they plotted to overturn the results of the 2020 election that Trump lost.
The former mayor faced a second indictment in Arizona the following spring alongside 17 others for a “fake electors” scheme that allegedly included pressuring county supervisors and local legislators to change the election’s outcome.
That December, a Washington, D.C. jury ordered Giuliani to pay $148 million to Ruby Freeman and Wandrea “Shaye” Moss, a pair of election workers from Georgia who were inundated with death threats and sent into hiding after he falsely accused them of committing ballot fraud to help Biden.
Giuliani’s election fraud claims led to the once-respected lawman’s permanent disbarment in New York and Washington, D.C., in the summer of 2024.
The former mayor’s lawyer and longtime confidant Bob Costello, who’s trying to help him get his law licenses back — and whose firm sued him in 2023 for $1 million in unpaid legal bills — came to Giuliani’s defense.
“You’re gonna disbar America’s mayor?” Costello said. “At the time, as I explained recently to Rudy, the guy was was making something like $6-8 million a year as a lawyer. So they deprived him of that $6-8 million a year for what, six or seven years now? That’s a lot of money. You shouldn’t be able to abuse anybody like that, much less a guy who was the U.S. attorney for the Southern District of New York and effectively wiped out the mafia and then was the mayor of the city of New York during 9/11. I mean, my god.”
Teflon Rudy
After staring down the possibility of federal prison time and financial ruin, Giuliani has appeared to make it out for the most part unscathed.
Manhattan prosecutors in 2022 announced criminal charges would not be forthcoming in the foreign lobbying investigation, and the indictments in Georgia and Arizona were dismissed after Trump retook power in 2024.
Submerged in debt, he came back from the brink of bankruptcy in 2025 after losing almost everything of value he owned when he reached an undisclosed settlement with the mother and daughter from Georgia he was found liable for defaming. Other lawsuits brought in relation to his election fraud claims were settled or dropped, and he got a pardon from Trump in November, saving him from facing any federal charges related to his efforts to thwart democracy in 2020 under future administrations.
The biggest threat to Giuliani’s finances now may be a suit brought by a woman who claims he sexually harassed and assaulted her during Trump’s first term after her hiring as his business assistant.
The pending case brought by Noelle Dunphy in Manhattan describes Giuliani as a chronic alcoholic who went on “alcohol-drenched rants that included sexist, racist and antisemitic remarks,” and likens the former mayor’s behavior around her to that seen in “Borat: Subsequent Moviefilm,” when he was caught on a hotel hidden camera with a young woman. Giuliani denies Dunphy’s allegations.
Last rites
After suffering a spinal injury in a bizarre car crash on a New Hampshire highway in September 2025, Giuliani had a second brush with death this past May, according to his 35-year-old spokesman Ted Goodman, who said he’d been by Giuliani’s side when he was read his last rites at a Florida hospital after experiencing complications from a restrictive airway disease contracted at Ground Zero.
The former mayor soon after joined many tens of thousands of New Yorkers who have filed for benefits through the World Trade Center Health Program, many of whom blame him for failing adequately to warn the public of the dangers of breathing the toxic air downtown in the months after the attacks.
Giuliani had insisted it was safe for first responders to continue working on what became known as “the pile” despite an October 2001 memo to one of his deputy mayors warning the city could face as many as 10,000 liability claims in toxic tort cases over the following decades.
Costello told The News there weren’t many people looking out for the ailing former mayor. The closest people to him are Goodman — who he was for a time living with and helps him produce his nightly webcast “America’s Mayor,” following its cancellation on WABC — and Maria Ryan, who has been described in various news reports as both his nurse and his girlfriend.
Goodman, Giuliani and Ryan did not respond to requests for comment.
Asked whether Trump or anybody at the White House was meaningfully supporting the elderly Giuliani, Costello said no.
“Trump announced that he’s going to give Rudy the Medal of Honor,” Costello said. “That hasn’t happened yet, but he said he’s gonna do it.”
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