Rudy Giuliani Had Quite The Age Gap With His Most Recent Ex-Wife

Rudy Giuliani's 10-year age gap with his third wife, Judith Nathan, is somehow the least messy aspect of their relationship. According to New York Magazine, the 55-year-old politician was a married man when he ran into 45-year-old Nathan at the Club Macanudo in New York in 1999. At the time, Giuliani had been married to Donna Hanover for nearly 15 years, and they had already welcomed two children. 

However, they apparently weren't on the former New York Mayor's mind when he met Nathan, as he told the New York Times in 2003 that he was drawn to her the moment he laid eyes on her. By their third meetup, Nathan was telling her mother that he was the one. "We simply were two people in love — never mind the extracurricular stuff that went on around us," she said, in apparent reference to her beau's wife. Per CBS News. After Giuliani filed for a divorce from Hanover in October 2002, she claimed that his "open and notorious adultery" had triggered the end of their marriage. 

Notably, in his second ex-wife's filing, she claimed that he had also cheated on her with Christyne Lategano-Nicholas, a former employee who was over two decades younger than him. However, Lategano-Nicholas and the disgraced lawyer claimed the allegation was false. And it didn't seem like Nathan was deterred by his alleged scandalous age-gap affair, either because she tied the knot with him in May 2003. By the time his third marriage imploded in April 2018, his strange past as a politician who had age-gap relationships and affairs had already caught up to him. And so, no one was surprised their divorce got messy.

During Rudy Giuliani's ex-staffer Noelle Dunphy's sexual harassment lawsuit against him, she presented an audio recording from December 2019 in which he admitted that he had been cheating on Judith Nathan for nearly two years with a married woman named Maria Ryan. In the recordings, the former New York Mayor can be heard lamenting about how his mistress, who is 21 years his junior, can't cut ties with her family because of her strong bond with them. 

Even worse, his alleged affair was affecting his relationship with his son, Andrew Giuliani, who warned him that they would be forever estranged if he chose to spend Christmas with his mistress' family. However, when Page Six published a report detailing one of their illicit meetups from March 2018, Rudy argued that he had already been essentially separated from his third wife at the time. The politician also insisted that he didn't have a physical relationship with Ryan.  

However, his estranged wife pushed back and claimed that he had indeed cheated on her. What's more is that in a November 2018 legal filing, Nathan alleged that Rudy had spent over $280,000 on Ryan in the seven months since she had filed for divorce. Although Rudy once had a stunning net worth, his legal woes still greatly changed his lavish life. By the time he signed off on divorce papers for the third time in December 2019, it was clear that the former Trump lawyer would never be able to live down the affair rumors.