The Truth About Rudy Giuliani's Three Ex-Wives

Let's start at the end, shall we? In this case in 2019, when Rudy Giuliani divorced his third wife, Judith, after 20 years together. 

Giuliani's marriage to Judith Giuliani (formerly Nathan) was the most soap-operatic of his three failed attempts at settling down. The pair rocketed into the public eye in 9/11's aftermath, when Judith took an active roll in relief efforts, manning call centers for victims (via The New York Times). They quickly became New York royalty and acted accordingly. According to The Washington Poston the private jets they took to public engagements, Judith's designer purse got a seat of its own. They owned box seats at the New York Yankees, bought high-value properties, and went to the opera. Judith, at one point, racked in a yearly salary of $125,000 for helping Giuliani write speeches (via Vanity Fair). She doesn't come from wealth — before Giuliani, she'd earned modest salaries as a hospital sales rep and a dental receptionist — but she fought to hold onto it. Despite receiving $42,000 a month in alimony, she fought for more, claiming at court that Mr. Giuliani had spent nearly $300,000 on an affair since their separation (via The New York Times). 

"I'm sad to know that the hero of 9/11 has become a liar," Judith told The New York Times. Rudy's problems with fidelity are hardly news to us. For one, Judith and Rudy's affair began while Rudy was married to his second wife, Donna Hanover. 

Donna Hanover found out her marriage to Rudy Giuliani was over via TV

Judith Nathan and Rudy Giuliani met in 1999 at a cigar bar, where Judith apparently offered Guiliani a business card. "Our attraction was instantaneous. There was almost something mystical about the feeling,' Giuliani told The New York Times

Back then, of course, Guiliani had been married since 1983 to television anchor and Law and Order star, Donna Hanover, with whom he had two children (via The Irish Times. Hanover had probably already weathered one affair by that time, but she had, according to a statement she made during her divorce "made a major effort" to keep the marriage together (via The New York Times). So in 2000, while Vanity Fair reports that she was aware of a "sudden mysterious chill" between her and Guiliani, her separation took her completely by surprise. It's now the stuff of legend. Hanover found out that she was separating in 2000, via a news conference (via The Washington Post). "They're all there to stay," an ex-staffer told Vanity Fair, "until they're gone. And the staff usually knows before they do."

Hanover got $6.8 million out of her divorce. During it, she accepted a part in The Vagina Monologues, wedding ring on. Was it a play at embarrassing Guiliani? The tabloids giggled. Then, in 2002, her high school sweetheart, Ed Oster, gave her a call. The two have been married since 2003 (via CBS).

Regina Peruggi's marriage to Rudy Giuliani ended after he cheated with Hanover

"I dare say we never had a first lady as contemporary, as smart, as personable as you," said David Remnick, editor of the New Yorker, during Hanover's last charity in the capacity as first lady to Mayor Rudy Guiliani (via The Irish Times). Hanover says that Guiliani swept her off her feet. Spoiler alert. He did so while still married to his first wife, Regina Peruggi, who was working as a drug abuse counselor at a state jail at the time (via Bklyner).  

Guiliani's 14-year marriage to Peruggi ended in 1983 (via The New York Times). They didn't get divorced. Instead, Peruggi and Guiliani's marriage was annulled on the grounds that they were second cousins once removed (yup), and hadn't obtained a church dispensation before marrying (via The New York Times). 

We don't have a lot of information about who Regina Peruggi was when she was married to Guiliani. We do know who she became after. Between 1990 and 2001, the educator served as the first lay president of Marymount Manhattan College, during which time she doubled enrollment in the institution (via Marymount Manhattan College). Between 2004 to 2013, she served as the first female president of Kingsborough Community College. During her tenure there, she was honored as a 2006 New York State Senate Woman of Distinction (via New York State Senate). She was, in other words, the educational equivalent of a rockstar.