Rudy Giuliani's $60M Divorce: This Time It's Going To Hurt

Contested, no prenup and a recent aversion to kicking up dirt in public. Call it karma or just bad timing, the deck on this split is deeply stacked against the tough-guy mayor. The best he can do is fight to a stalemate.

After Rudy Giuliani’s wife preemptively filed the paperwork to end the marriage, the only silver lining was that the details of the proceedings will remain confidential.

But from the key players’ track record and what they’ve leaked so far, we might end up hearing a lot more than what normal courtroom decorum allows.

And with an estimated $60 million at stake this time, what we hear could get ugly.

Expert combatants

Rudy is no stranger to no-holds-barred divorce. When he hooked up with current wife Judith, he dragged Donna Hanover through the tabloids.

Even though he was technically the adulterer, he accused Donna of cruel and inhuman treatment while kicking her out of the New York City mayoral mansion and sabotaging her charities.

Right now he’s playing the good cop card. Reporters are hearing about how he’s eager to get mutual disclosure, how neither party is completely innocent, the whole routine.

Unfortunately he’s not the one who fired the first shots. Judith filed the paperwork and she indicated that the split would probably be anything but easy.

She’s willing to put up a fight. Like her soon-to-be-ex-husband, this is not her first contentious divorce. Years before she met Giuliani, she was married to a Long Island trust fund baby. When that relationship went south, both sides got nasty.

All in all, she won her last divorce and he lost his. Donna ended up squeezing $6 million out of Rudy, which amounted to about half of his paper assets plus a year of his high-powered post-911 speaking fees.

Judith got custody and support last time. Odds are good Rudy’s going to settle this time around.

Who has more to lose?

Rudy has been awfully quiet since the election. Technically he’s the White House cybersecurity consultant but the job is extremely low profile by his standards.

Whatever’s going on in his life, he isn’t eager to have it hit the headlines. Unless that attitude shifts, he’s playing defense here.

Back in 2000, he was eager to fight it out in the morning papers. The split took two years of insults and petty retaliation against his wife, his kids and ultimately the city. It took 911 to turn him into a hero.

This time around, I think he’s more inclined to pay Judith to go away and keep her mouth mostly shut. He’s still got national political ambitions. A really nasty divorce in the age of #MeToo would end his career with a bang.

That said, he’s 73 years old. He could stay on the consulting circuit until he drops dead, but statistically his peak earnings years are behind him. A contested divorce hearing is going to consider his assets in terms of retirement and not so much where future opportunities will take him.

Do the math, he might’ve banked $60 million since leaving the mayor’s office. By 2002 he was taking in $8 million a year. Since then he’s bought his way in and out of a few firms, cashing bigger and bigger checks.

But at this point, he’s cashed out of just about all the ventures: Giuliani Partners, Giuliani Capital, Bracewell Giuliani. The security company is still around, but it’s unclear how much business it actually does.

He’s collected his big paydays. Now a divorce decree can take a hefty chunk of that wealth away from him in his golden years.

Remember, when he left Donna he claimed he was practically insolvent. The money started coming in once Judith came into the picture. All the wealth he has now, he earned while he was married to her.

That’s not an instant 50-50 judgment in New York, where separate property still applies. But if the case goes to court, her participation in his success will be a factor.

Judith could end up with $30 million if it goes all the way. While his lawyers might buy her out with a lower number, it’s still going to hurt.

Nuclear options

If Judith is as serious now about winning as she was in her last divorce, look for allegations of abuse to emerge. True or false, Rudy doesn’t have a lot of leverage in that scenario.

She has more to win and he has more to lose. While he paid her $125,000 a year for writing speeches early in the marriage, she never really earned real money like he did.

And she’s only 10 years younger than he is, so retirement is on the horizon for her too. This is her chance to lock down the finances for the rest of her life.

The kids on both sides of the blended family are grown. His son seems friendly but both his daughter and hers appear to be more than a little estranged.

Any estate planning he wanted to do is going to get dragged into this. After all, there’s no prenuptial agreement — he’s made that clear — because when they married, he didn’t have much. His previous divorce took whatever was already there.

A prenuptial agreement would’ve protected the kids’ inheritance. They’ll probably do all right either way, but the split is going to be a lot smaller for everyone now.

On the other hand, Judith could have simply hung on to inherit as spouse, saving everyone the disruption of a divorce. The fact that she’s breaking it off now reveals how much she’s learned to hate him. 

It’s in his interest to keep her motives out of the public eye. He’ll settle.



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