Rudy Giuliani. You probably know him as "America’s Mayor" or the guy who was once Donald Trump’s right-hand man. But honestly, if you live in New York—or even if you just read the tabloids—you know his personal life has always been a complete whirlwind. His relationship history isn't just a list of names; it’s a series of public explosions.
People talk about "Rudy Giuliani and wife" as if there’s just one person, but there were three. And each exit was more dramatic than the last. We’re talking about an annulment based on being second cousins, a divorce announced via a televised press conference, and a third split involving allegations of six-figure spending on a mistress.
It’s messy. It’s complicated. And it’s kind of a masterclass in how not to handle your private business when the cameras are always on.
The First One: A Marriage That Was Actually Illegal?
Long before he was a household name, Rudy married Regina Peruggi in 1968. They were together for over a decade. But here’s the kicker: they were actually second cousins.
Now, they claimed they didn't know this at first. Or maybe they thought they were third cousins? Either way, when the marriage hit the rocks in the late '70s, Rudy didn't just want a divorce. He wanted an annulment from the Catholic Church.
Basically, he argued the marriage was never valid because of the blood relation. The Church eventually agreed in 1982. This move was pretty convenient because it allowed him to remarry in the Church later. Regina went on to have an incredible career in education, eventually becoming the president of Kingsborough Community College. She rarely, if ever, talked about him. Classy move on her part, really.
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Donna Hanover and the Divorce by Press Conference
If you think the cousin thing was wild, the Donna Hanover era was a full-blown soap opera. Donna was a TV personality and actress. They married in 1984 and had two kids, Andrew and Caroline. For years, they were the ultimate New York power couple.
But by the mid-90s, the cracks were everywhere. Rumors of affairs were constant. There was the whole thing with his press secretary, Christyne Lategano, which they both denied. But then came May 2000.
Imagine being Donna Hanover. You’re the First Lady of New York. You’re living in Gracie Mansion. You turn on the TV and see your husband holding a press conference. He tells the entire world he’s separating from you.
He hadn’t told her first. He literally announced their separation to the media before he mentioned it to his wife. It was brutal. Donna fired back with her own press conference outside Gracie Mansion, basically saying she had tried to keep the marriage together despite his "notorious adultery."
The legal battle that followed was legendary. At one point, Donna’s lawyers tried to get a restraining order to keep Rudy's girlfriend—a woman named Judith Nathan—from entering Gracie Mansion. Eventually, they settled in 2002. Rudy paid her a reported $6.8 million.
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Judith Nathan: The Third Act
Enter Judith Nathan. She was the woman Rudy was seeing while still technically married to Donna. They married in 2003 in a massive ceremony at Gracie Mansion, officiated by Mayor Michael Bloomberg.
For a while, Judith was his partner in everything. She was by his side during his 2008 presidential run. They seemed solid.
Then came 2018.
Judith filed for divorce after 15 years. This wasn't a quiet split. The court filings were like something out of a movie. She accused him of spending over $280,000 on his mistress, Maria Rosa Ryan, in just six months. She claimed he was dropping thousands on cigars, luxury pens, and travel while telling the court he couldn't afford to pay her spousal support.
At one point, his lawyers even argued that he was "working for free" for Donald Trump and therefore didn't have the income to meet her demands. The judge wasn't exactly thrilled about the "dirty laundry" being aired in public. They finally settled in 2019, though the exact numbers are under wraps.
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Why This Still Matters in 2026
You might wonder why we're still talking about this. Honestly, it's because Rudy's personal life has always mirrored his political style: aggressive, public, and often chaotic.
As of early 2026, Rudy’s financial situation has become a major headline due to massive legal judgments against him. In his bankruptcy filings, the name Maria Ryan—the woman Judith accused him of seeing—has popped up again. While he’s denied they are a "romantic" item, she’s been described as his partner or close associate in various legal contexts.
It’s a pattern that has repeated for forty years.
What We Can Learn From the Chaos
If there's any takeaway from the saga of Rudy and his wives, it’s these three things:
- Public perception is a double-edged sword. Rudy used his family image to build a brand, but when that image shattered, it happened in the most public way possible.
- The "Press Conference Strategy" rarely works. Trying to get ahead of the story by blindsiding your partner usually backfires. It didn't make Rudy look strong; it made him look cruel to a lot of New Yorkers.
- Legal settlements are long-lasting. Even years later, the fallout from these divorces continues to impact his current financial struggles and bankruptcy proceedings.
If you’re following the current news about his assets and legal battles, keep in mind that the "wife" narrative isn't just gossip—it's the backstory to how he ended up in his current legal and financial position. The past, especially in New York politics, never really stays in the past.
For those looking to understand the full scope of his current legal situation, the next step is looking at how these past settlements are being treated in his ongoing 2026 bankruptcy proceedings.