All Giuiliani’s Wives – Love and Loathing in New York City

Former NYC Mayor, now latest Trump defender, Rudy Giuliani’s nasty divorce from his third wife Judith is not the first scandalous split in the politician’s life.

His previous marriages, to an alleged second cousin and to an actress - TV personality, also gave the tabloids endless material for shocking headlines and rumor amplification.

Often criticized by conservatives for his many known affairs and divorces, Giuliani reportedly did not make the latest Mrs. Giuliani sign a prenup, and perhaps, he is lamenting that now. A look at his love and loathing stories offers a glimpse into high net-worth divorce in New York.

Rudy Giuliani’s Wife Number Three: Judith Nathan

Date of marriage: May 24, 2003

Date of divorce: Filed in April 2018

Children from the marriage: None

Life and Career:  Judith Nathan came from humble origins and was struggling to support her daughter Whitney in New York when she met Giuliani. Although she spread the notion that her second husband, Bruce Nathan, was a millionaire and a trust fund baby, Vanity Fair found that he made little over $70,000 during the year leading up to the split.

She is a registered nurse, and did abundant charitable work while married to the former mayor but Judith only worked briefly as a nurse during the few months following graduation in Pennsylvania, where she was born.

Her first marriage to a young colleague ended amicably after four years, but her divorce from Nathan got rather ugly, including a custody battle.

Love Story: Giuliani met Judith at a cigar bar in 1999, while he was still married to his previous wife. They dated secretly for a year, before he announced he was leaving his wife during a press conference.

Around the time of their wedding, Judith commented, "Hopefully if you learn anything from being married before, it's that you learn from your mistakes. We look forward to growing old together." She also came from two previous marriages, but lied to the press about only having been married once before.

Known scandals: Recently, Giuliani made a tasteless remark about Hillary Clinton’s figure at Trump’s resort Mar-a-Lago. This prompted Judith to give him a “foul look.” 

The remark she did not appreciate was, "Hillary was also here. And she actually fit through the door." Giuliani was speaking to an audience of Republican Party donors.

To crown the faux pas, Trump said, in his own speech to the crowd, "I'm just glad I didn't say it."

While Giuliani campaigned to become the Republican nominee for the presidential run in 2008, Judith earned a reputation as a woman who splurged on all kinds of luxury items. Vanity Fair famously reported that she once demanded an extra seat on a plane for her Louis Vuitton handbag. 

Reasons for divorce: Unknown, sources close to the couple have commented, "How'd they stay married for 15 years? That's a better question!" 

Asset distribution issues: The former couple owns properties in Southampton, Manhattan, and Palm Beach, Florida. The fight over assets is ongoing at Manhattan Supreme Court. Both sides have demanded details about the other party’s current net worth. 

In official documents filed in 2007, Giuliani valued his fortune at $30 million. As per current estimates, he could be worth $60 million today.

Public comments about the divorce: A spokesperson for Judith commented, "She is thankful that she was able to be by Rudy's side on Sept 11th, 2001, and help establish the Family Center at Pier 94 which supported the victims' families for several months, and also be a founding board member of the Twin Towers Fund. As a nurse she found this particularly gratifying."

Rudy Giuliani’s Wife Number Two: Donna Hanover

Date of marriage: April 15, 1984

Date of the divorce: First filing, 2000, finalized in 2002.

Children from the marriage: Andrew and Caroline, 15 and 11 at the time of the divorce.

Life and career: Originally from Oakland, California, Hanover is the daughter of a high-ranking Navy officer. She graduated in political science from Stanford and later obtained a Master’s Degree in Journalism from Columbia.

A journalist, TV personality, and actress, Hanover is famous for her appearances on WOR radio and the Food Network. She was very active during Giuliani’s campaign and later in her role as the First Lady of New York City, promoting many health and educational causes. 

She became an actress in the mid 1990s, appearing in several films, landing a recurring role in Law & Order and also appearing on Sex and the City and Ally McBeal, among other popular shows.

Her first husband was Stanley Hanover, a Harvard graduate whom she met at Stanford.

Known scandals: Rumors of Giuliani’s affair with Judith Nathan abounded when he decided to end them with an unlikely choice: holding a press conference. 

Giuliani announced the split from Hanover to the world without giving her a heads up. This caused the couple’s children to be estranged from him for many years.

Following their scandalous separation, Hanover obtained a restraining order preventing Guiliani’s then girlfriend, Judith Nathan, from getting anywhere near Gracie Mansion, the New York Mayor’s official residence. 

At the time, Giuliani commented, “In these divorce situations, you cannot place blame, it is 50/50, there are problems on both sides.”

Reasons for the divorce: Adultery

Asset dispute: During divorce proceedings, Giuliani claimed he only had $7,000 in the bank. However, when the divorce was finalized, Hanover was awarded $6.8 million and custody of their two children 

Donna’s story beyond Giuliani: In 1968, Ed Oster dumped his high school girlfriend, Donna Hanover, during their freshman year at Stanford. Hanover was heartbroken. One year after she divorced Giuliani, Oster called her up, out of the blue.

Donna later told reporters that Ed said, “he was divorced, was going to be in town for some business. Would I have coffee with him? So, we took a long walk in Central Park, and he said to me, ’I’m so sorry I made you cry all those years ago.’”

Soon after, in 2003, Donna and Ed were married. “This is my lost treasure. My lost treasure found, never to be lost again,” he said.

Mrs. Giuliani Number One: Regina Peruggi

Life and career: The daughter of his father’s first cousin, Peruggi was therefore Giuliani’s second cousin. 

She grew up in The Bronx and attended Catholic schools, graduating from New Rochelle in 1967. Peruggi had a remarkable career as an educator. She was the first woman to preside over Kingsborough Community College, a position she held between 2005 and 2014.

Wedding date: October 26, 1968

Divorce date: Filed (by Giuliani) and finalized in 1982.

Annulment: A church dispensation allowing second cousins to marry was a requirement for the couple’s Roman Catholic wedding to be valid. So, Giuliani was able to secure an annulment.

Scandals: Giuliani denied knowing he and his first wife were second cousins, claiming he believed they were actually third cousins. 

Children from the marriage: None

It remains to be seen how many millions Judith Nathan will be able to get from Giuliani. After his experience with his previous divorce, it is likely that he is going to settle before the scandal escalates.

Recently, John Oliver dedicated his weekly show to Giuliani, who is now Donald Trump’s attorney and sometime fall guy. With Oliver’s characteristic sort of humor, he compared the two, saying,

“Think about it: They’re basically two versions of the same person. They’re both New Yorkers coasting on their reputations, they’ve both had three marriages, neither of them can shut up in front of a camera, and, perhaps most importantly, they both want... Ivanka—which is weird for Trump because Ivanka is in his family, and is weird for Giuliani because she isn’t.”

In spite of having married his second cousin and having practically announced his affair to his wife during a press conference, Giuliani seems to keep landing on his feet. It will also be interesting to see whether he already has a candidate for Mrs. Giuliani Number Four...


Dror Bikel

Dror Bikel co-founded Bikel Rosenthal & Schanfield, New York’s best known firm for high-conflict matrimonial disputes. A New York Superlawyer℠ and twice recognized (2020 and 2021) New York Divorce Trial Lawyer of the Year, Dror’s reputation as a fearsome advocate in difficult custody and divorce disputes has led him to deliver solid outcomes in some of New York’s most complex family law trials. Attorney Bikel is a frequent commentator on high profile divorces for national and international media outlets. His book The 1% Divorce - When Titans Clash was a 5-category Amazon bestseller.

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