The man who once held a Washington hearing room’s attention as “America’s mayor” ended up listening to a disciplinary lawyer ask: “I don’t know if something happened to Mr. Giuliani or what.” Hamilton “Phil” Fox III, who prosecuted the disbarment case in D.C., said it was as if there were two different people.
Prosecutor
Rudy Giuliani was born in Brooklyn in 1944, the only child of working-class parents. His father, Harold, did time in Sing Sing for felony assault and robbery. Giuliani graduated from NYU Law in 1968, and in 1981 became U.S. Associate Attorney General under Reagan. Two years later he took over as U.S. Attorney for the Southern District of New York, technically a step down, because he wanted to try cases himself.
It made his name. His office won convictions against the Wall Street figures Ivan Boesky and Michael Milken, and he is credited with bringing the “perp walk” into common use. In the Mafia Commission Trial of 1985 and 1986 he indicted eleven organized crime figures, including the heads of New York’s Five Families, under the RICO Act. “Our approach is to wipe out the five families,” he said. Critics noted the other side: arrests of white-collar suspects at their desks, like the trader Richard Wigton, led away in tears, with charges dropped within three months.
City Hall
He lost the 1989 mayoral race and won in 1993, reelected in 1997 with 57 percent. He ran on a tough-on-crime platform, brought in William Bratton as police commissioner, and led what the city called a civic cleanup that ran from 1994 to 2001. It was controversial. After the September 11 attacks, his leadership earned him the name “America’s mayor,” a knighthood and Time’s Person of the Year for 2001.
He left a 2000 Senate race against Hillary Clinton after a prostate cancer diagnosis. In 2002 he founded Giuliani Partners, a security consultancy, and in 2005 joined the law firm that became Bracewell & Giuliani. His 2008 presidential run began with him as an early frontrunner and ended in poor primary results and an endorsement of John McCain. Biographer Andrew Kirtzman sees that failure as the turning point. Giuliani fell into a deep depression, and Trump put him and his then-wife Judith up in a Mar-a-Lago bungalow for a month.
Trump’s Lawyer
In 2016 Giuliani became a leading Trump surrogate, and in April 2018 he joined the president’s personal legal team. His Ukraine contacts figured in Trump’s first impeachment, and federal agents raided his home and office in April 2021, though that probe ended without charges.
After the 2020 election he represented Trump in lawsuits seeking to overturn the result, pushing false claims about rigged voting machines and polling-place fraud. One news conference on Pennsylvania challenges was held outside Four Seasons Total Landscaping, next to a crematorium and a pornography shop. On January 6, 2021, he told supporters who would later storm the Capitol that they should seek “trial by combat.”
The consequences stacked up. A federal jury in Washington awarded $148 million to two Georgia election workers, Ruby Freeman and Shaye Moss, whom he had falsely accused of fraud. “I was afraid for my life,” Moss told jurors. After the verdict Freeman said: “I can never move back into the house that I call home.” He tried and failed to declare bankruptcy, and later reached a settlement to pay the damages.
In August 2023 he was indicted in Georgia alongside Trump and 17 others under the state’s RICO law, once his own favorite tool against mobsters. An Arizona indictment came in April 2024. He was disbarred in New York in July and in the District of Columbia in September; a D.C. panel had said his misconduct “sadly transcends all his past accomplishments.” In November 2025, Trump issued him a federal pardon.
Sources
- Rudy Giuliani – Wikipedia
- Rudy Giuliani: What Happened to America's Mayor?
- The fall of Rudy Giuliani: How ‘America’s mayor’ tied his fate to Donald Trump and got indicted
- Rudy Giuliani
