All Of The Cheating Drama That's Surrounded Rudy Giuliani

Rudy Giuliani hasn't been in a marital relationship that wasn't tainted by scandal in some way. His first marriage with Regina Peruggi had some bizarre controversy attached to it when it was discovered Peruggi was the former New York mayor's second cousin. Giuliani reportedly separated from Peruggi in 1974 after he discovered their genetic link. But somehow, that scandal paled in comparison to the hot water he'd find himself in with his second wife Donna Hanover. Hanover was a news anchor when she met Giuliani, and they'd later end up marrying in 1984.

But Giuliani's commitment to Hanover was called into question when he was accused of having an affair with Cristyne Lategano, his former press secretary and mayoral aide, in 1995. Both Lategano and Giuliani would deny the rumors. "Allegations by unnamed sources are not true, and there is no need to comment on malicious works of fiction," Lategano once told a reporter according to the New York Post. "When a woman works closely with her male boss, it's called intimate. When a man does the same, it's called loyal."

Although Giuliani's purported affair with Lategano was up for speculation, his affair with Judith Nathan wasn't. Giuliani met the registered nurse at a bar through a mutual acquaintance. By 1999, it was reported that they were having an affair. On May, 11, 2000, Giuliani hosted a press conference announcing his plans to break up with Hanover without informing his ex-wife beforehand. The pair finalized their divorce on July, 2002.

Rudy Giuliani and Judith Nathan were married for over 16 years before their divorce in December 2019. Giuliani's old habits came back to ruin their marriage, however, when rumors started circulating that Giuliani was in a relationship with Maria Rose Ryan.

Eventually, Giuliani hoped to clear the air by providing details about a two-day meeting they had at a New Hampshire resort. "I think this occurred on March 29 and I was separated on April 2, so I had a pretty good inkling of it [the divorce,]" he told the New York Daily News (via The Providence Journal). He maintained that he and Ryan were only friends, reassuring that any interaction they had with each other was strictly business. Giuliani's ex-wife, however, was adamant. "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 said in a 2018 statement according to Page Six.

However, The Independent published excerpts from a conversation Giuliani was having with former employee Noelle Dunphy that was secretly being recorded. The recording was used as evidence in a lawsuit Dunphy filed against the Republican for sexual assault and harassment, which ended up outing his affair with Ryan. During the conversation, Giuliani can be heard saying in regards to Ryan, "We've had this, like, affair for two years and I'm friendly with her husband."