In the “What on earth happened to Rudy Giuliani?” sweepstakes, there are plenty of entries but no winners. Everyone wants to know why “America’s Mayor” became President Trump’s favorite consigliere.
Absolutely not, Rudolph W. Giuliani tweeted last week, writing that The Washington Post stooped “so low as to actually ask me about my pending divorce, to see if it affects my work. It doesn’t.”
Giuliani’s private life has been splashed across New York tabloids for decades, and the lawyer representing his estranged wife thinks Giuliani is concealing money while working pro bono for President Trump. As a central figure in the Ukraine impeachment scandal, the exact nature of Giuliani’s clients and income is of interest to more than divorce lawyers.
Not that he wants to talk about any of it.
“My divorce is my personal business,” Giuliani texted me last week. “Anyway my opinion on it is the least objective as is my soon to be ex-wife. This is third divorce for both of us and thank goodness no children. If you can figure out the truth in a divorce proceeding, you should be on the High Court, the one above the Supreme Court.”
It’s hard to explain why a marriage falls apart, or why two crazy kids once madly in love end up going at each other’s throats.
“I feel betrayed by a man that I supported in every way for more than 20 years,” Judith Giuliani told the New York Times last month. “I’m sad to know that the hero of 9/11 has become a liar.”
There’s never a good time for a nasty split, but perhaps this is the very worst of times for Giuliani.
“He’s going through a divorce at the same time he’s in the most precarious legal and professional situation of his life — and it’s all happening on live TV,” says Rebecca Katz, a New York political consultant. “And there doesn’t seem to be anyone left in Trump’s orbit with the inclination or authority to stop him.”
Giuliani, 75, is leaving this marriage the same way he entered it: with blaring headlines, tabloid updates and so much drama.
“He digs it,” says Ken Frydman, spokesman for his 1993 mayoral campaign. “He loves the attention. It’s sport for him — and a lack of judgment.”
In May 2000, New York’s two-term mayor called a news conference and announced a separation from his second wife, television anchor Donna Hanover. It was also a public acknowledgment of his year-long relationship with Judith Nathan, whom he praised as a “very, very fine woman.” The separation, however, was allegedly a surprise to his wife, who said she found out her 16-year marriage was ending by watching television.
A surprise, but also not surprising: Hanover started dating Giuliani when he was married to his first wife, Regina Peruggi. An eternal mystery: When the mistress becomes the wife, why is she shocked when another mistress enters the scene? (“Job opening,” goes the old joke.) The New York papers alluded to other indiscretions, but nothing serious became public until the infamous news conference.
Nathan and Giuliani met in 1999 at Club Macanudo, an East Side cigar bar. Nathan, divorced from her second husband, was a hospital sales rep and a trained nurse. Across the room: Mayor Giuliani. Sparks flew.
“It was the thunderbolt,’’ he told the New York Times. “Our attraction was instantaneous. There was almost something mystical about the feeling.’’
Soon, the two were inseparable, except for the quality time he spent with his wife and two children.
The affair was not, shall we say, discreet. Nathan accompanied the mayor to a number of official functions and stayed at his side during his treatment for prostate cancer, which led to his divorce lawyer’s TMI revelation in 2001 that the cancer had rendered Giuliani impotent and the two had not had sex for a year. They were not ones to let the marriage of true minds admit impediments, so love flourished.
Giuliani and Hanover divorced in July 2002, and he married Nathan the following May in a ceremony at Gracie Mansion fit for royalty: The bride wore off-white and a tiara; the 400 guests included Yogi Berra, Henry Kissinger, Barbara Walters and Trump.
By this time, Giuliani had been crowned “America’s Mayor” and Time’s 2001 Man of the Year, following his heroic response to the terrorist attacks of Sept. 11, 2001. He received a knighthood from Queen Elizabeth II. Prevented by law from seeking a third term as New York’s mayor, he settled into life with Nathan as a celebrated power couple.
For the first time in his life, Giuliani was really rich. He was merely rich before — the divorce settlement gave Hanover more than $6 million — but now he was raking in serious bucks, commanding $100,000 per speech and private jets to fly in style. His bride accompanied him on all his trips; they required extra accommodations for staff — and an extra airplane seat for Judith Giuliani’s designer purse, which she was unwilling to put on the floor, according to news reports. Old friends of the former mayor allege they were pushed aside when his new wife turned Giuliani into a country club kind of guy.
“They were absolutely a good match,” says Frydman, who says that Giuliani is not the same man he knew 25 years ago. “They’re equally unsympathetic: People hate Judith and people hate Rudy.”
And they were equally ambitious: For a brief shining moment, Giuliani was the Republican front-runner for the 2008 presidential nomination. There were glowing profiles of the couple, complete with musings in New York magazine about what they would be like as president and first lady.
His presidential bid was thwarted by Sen. John McCain, and the Giulianis resumed life as Republican VIPs, buying properties — an elegant apartment on East 66th Street, homes in Palm Beach, Fla., and the Hamptons — and portfolios. There were box seats for the Yankees and the opera, private jets, Cuban cigars. Along the way, he amassed a fortune estimated at $45 million, according to several media reports.
When it came to politics, Giuliani hung around in the background, until 2016, when he endorsed Trump because of their longtime New York connections and popped up as a featured speaker at the Republican convention.
In April 2018, he was named one of the president’s personal lawyers, the same month Judith Giuliani filed for divorce in Manhattan Supreme Court.
“I don’t know that we can blame Rudy’s current meltdown on the divorce,” says Katz. “It seems more likely that Rudy’s meltdown led to the breakdown of his marriage, rather than the other way around.”
What happened in the marriage? And when did it happen?
“It was an ongoing process that began when he lost the presidential campaign,” Judith Giuliani told New York magazine last year. And then the coup de grace: “For a variety of reasons that I know as a spouse and a nurse he has become a different man.”
(As a nurse? Low blow.)
Through her lawyer, Judith Giuliani declined to be interviewed for this article. But she was more chatty last year amid rumors that her husband was dating Maria Rosa Ryan, a hospital administrator whom he took to the White House state dinner just weeks ago. The two have traveled abroad extensively and shared a night last year in a New Hampshire hotel, where he claims they were watching “The Godfather.” Giuliani and Ryan say the relationship is not romantic.
Shortly after the New Hampshire screening, Judith Giuliani released a statement to the New York Post saying, “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.”
Divorce filings in New York are not public documents, but enough has come out in news reports from the open hearings, which are vigorously covered by the New York tabloids.
Judith Giuliani, 64, receives $42,000 a month in alimony, an amount she claims is peanuts compared with the $230,000 per month they spent as a couple, according to the New York Times. Her lawyer, Bernard Clair, reported that Giuliani earned millions working at the law firm Greenberg Traurig: Almost $8 million in 2016 and $9 million in 2017. He also claims that by working pro bono for Trump, his client’s husband is deliberately concealing income and working with people who will have to “reimburse him” at a later date.
Giuliani, on the other hand, is pleading poverty. Because he is working for free and paying his own expenses, his lawyer says he can’t afford to support his wife in the lifestyle to which she became accustomed and had to borrow money to pay taxes.
“My reason for working for President Trump for free is wholly and entirely patriotic, and also because he is my friend,” he told the New York Post.
Meanwhile, they’re reportedly fighting over everything: money, Christmas decorations, remote controls and who gets to hang out in which of the private clubs to which they belong.
Judge Michael Katz told the couple: “It is beyond me why either party in this case would have an interest in having all of this done publicly.” Settling, he said, “would treat their relationship and marriage with more respect than divulging all our dirty laundry out for public consumption.”
That’s not happening. There is some chatter in New York that Judith Giuliani is writing a book — or it might be a savvy negotiating tactic for someone with no prenuptial and a good memory.
The Giulianis’ next court date is scheduled for January.
