Former Trump Lawyer Rudy Giuliani Will Never Live Down The Affair Rumors

Few political figures have been mired in more controversy than Rudy Giuliani. The once-respected lawyer and former New York City mayor has been involved in so much personal drama and legal hot water that his formerly lavish lifestyle is a thing of the distant past. He's been arrested – complete with an embarrassing, tragic mugshot – and he's even been disbarred, making him Donald Trump's worst-ever lawyer (at least for a time). However, despite all his career setbacks, it's the multitude of weird, off-putting, and embarrassing romance scandals that Giuliani will likely never live down.

After a lifetime of high-profile drama surrounding his love life — including the revelation that his first wife, Regina Peruggi, was actually his second cousin == Giuliani has been through three marriages, all of which ended in public awkwardness and humiliation. Giuliani's second marriage, to Donna Hanover, with whom he shares adult children Andrew and Caroline, came to an end in 2002, when their divorce was finalized following two years of contentious court battles, and three years after Giuliani began a secret adulterous romance with Judith Nathan.

Giuliani and Nathan would go on to tie the knot in May 2003, and that marriage would last for nearly 15 years until Nathan filed for divorce in April 2018. Shortly after, rumors started to spread that Giuliani had been having an illicit fling with a married woman named Maria Ryan. The former political operative allegedly bragged to his friends that he was seeing a woman that he crassly described as having "big boobs," Page Six reported in June 2018. While Giuliani denied rumors that he and Ryan were involved, the rumors are hard to shake for a man who is also being sued for $10 million for sexual harassment and assault by a former female employee.

In 2023, one of Rudy Giuliani's former employees, Noelle Dunphy, filed a 69-page complaint against the embattled lawyer and political pariah. The $10 million lawsuit alleges that Giuliani created an intensely hostile work environment, forced her to perform sex acts with him, and was often drunk. The lawsuit claims that Giuliani would go on "alcohol-drenched rants that included sexist, racist, and antisemitic remarks" (via Reuters). As it turns out, Dunphy had secretly recorded some of the interactions with Giuliani, and the incredibly disturbing transcripts of those recordings were made public as part of the lawsuit.

In between all of the awful things Giuliani said to Dunphy, according to the transcripts, he also reportedly made several references to his alleged mistress, a married woman named Maria Ryan. In the transcripts (per The Independent) Giuliani reportedly commented: "She has this tremendous connection to her family, and she loves me. But she can't leave her family, including her husband." Giuliani claimed to be "friendly with her husband," Robert Ryan. At one point, Giuliani even reportedly said he'd spoken with his mistress about the possibility of getting married at some point, and he claimed that she asked if her current husband could live with them.

Ryan has denied the claims that she and Giuliani have been seeing one another romantically, as did Giuliani's rep, Michael Ragusa. "Dr. Maria Ryan is Mayor Giuliani's business partner and nothing more," Ragusa said in a statement to Newsweek in June 2024. "Any reports of her being his girlfriend are false rumors made up by the mayor's enemies to damage his reputation."

When confronted about his alleged affair with a married woman in 2018, the perpetually embattled Rudy Giuliani said that the woman was just a friend of his. Giuliani's third ex-wife, Judith Nathan, claimed that wasn't true. "My husband's denial of the affair with the married Mrs. Ryan is as false as his claim that we were separated when he took up with her," Nathan told The New York Post. While Giuliani claimed to the outlet that he and Nathan were "in effect separated" when he spent a cozy weekend with his alleged mistress in April 2018, there was no legal period of separation noted when Nathan filed for divorce days later.

Giuliani's divorce from his second wife, Donna Hanover, wasn't any less messy. In 2000, Giuliani held a huge press conference in Bryant Park to make the big announcement that he and Hanover were getting a divorce. This was somewhat surprising news for the reporters and it was especially surprising for Hanover, who had not been informed of the press conference at all, and had no idea that Giuliani was intending to announce his divorce plans.

Giuliani's acrimonious split from Hanover got ugly, fast, and was drawn out in legal battles. Hanover's lawyer, Helene Brezinsky, argued that Giuliani was crafting a false narrative about the failure of their marriage and issued a statement when Hanover filed for divorce herself. "If there's going to be a divorce, let's have the truth about why – Rudy's open and notorious adultery," Brezinsky said in June 2002 (via CBS News). Despite a long career in politics, law, and public service, it seems like Giuliani's name will likely forever be synonymous with affair scandals and sexual misconduct claims.