Life without HER HUSBAND
Judge Judy Sheindlin’s fortune has grown to $400 million with a new deal, but she often finds herself alone
Judge Judy Sheindlin had a reason to celebrate — a few hundred million reasons, in fact. On Aug. 8, it was announced that she’d not only struck a deal to sell her library of more than 10,000 Judge Judy episodes to CBS for $95 million to $100 million, but had also extended her contract through the 2020– 2021 season for a payday of nearly $50 million a year. The next night, Judy and a few family members headed out to dinner at Milos in NYC to revel in her news as they feasted on octopus, salad and fish at a corner window table, an eyewitness tells In Touch. As they left, a photographer asked the 74-year-old if she’ll ever slow down. Her response? “You go until you stop!” That’s exactly what she intends to do, even if it means she’ll be apart from her husband. Re-upping through her 25th season means Judy will spend chunks of time away from Jerry Sheindlin, the former New York State Supreme Court justice whom she wed in 1977, divorced and then remarried. Spending time apart because of her new deal is causing problems in their marriage, insiders claim. Jerry wants Judy to retire, but Judy looks at him
like he’s from Mars for even asking, a friend tells In Touch. “She’s signed on to continue Judge Judy for another four years, and she isn’t stopping there. She’s open for another contract extension after the current one expires.” Friends are so concerned for the couple that some worry the judges are headed for another divorce (they split in 1990 before remarrying the following year) — which would mean a bitter fight over Judy’s $400 million fortune. It could turn into the most epic celebrity divorce Hollywood’s seen in years.
Are they growing apart again? “Jerry turns 84 this fall, and frankly, he can’t keep up with Judy’s whirlwind life,” says the friend. “It’s like Judy is a high-speed train and Jerry’s been left at the station. Judy is a force of nature in her career.”
For tough-talking Judy, her career is worth far more than a massive paycheck. She’s TV’S highest-paid personality with an Emmywinning show that’s been the No. 1– ranked program in syndication for the past eight years, and “she likes the power and the prestige that comes with it more than the actual money,” explains the friend. “Judy still remembers those days she worked as a New York family court judge when money was a big concern, especially since they were trying to raise a family [ her two kids and Jerry’s three from their first marriages] in such an expensive city.” Now, she doesn’t have to answer to anybody.
She’s often spotted out without Jerry in Greenwich, Conn., where they reside. “She comes in here a lot, and she’s always alone,” an employee at Sephora tells In Touch. She rolls up in her Bentley at Saks Fifth Avenue, “And she always comes solo,” says a store insider. “She keeps to herself. I mean, you know who she is as soon as she walks in; she has a very distinct look! She’s definitely not a shopaholic. There are plenty of instances where she comes in just to browse and doesn’t make a purchase.” Does she ever check out the sales rack? “Who doesn’t love a good sale rack?!”
Adding to the tension in the marriage is the lingering resentment
over Jerry’s infidelity with a wait- ress who’d served both him and Judy breakfast several times. His 2002 affair with Kary Farrell, who’s 25 years younger than Jerry and worked at a diner near the couple’s Florida home, “still looms over their marriage,” says an insider. “It’s been 15 years, but I don’t know that Judy ever fully got over that betrayal.” (Jerry would have done well to remember Judy’s words in her 1999 book Beauty Fades, Dumb Is Forever: “Women have memories like elephants — they never forget,” she wrote.)
While Judy had become the queen of daytime TV since Judge Judy debuted in 1996, Jerry’s efforts to follow in her footsteps failed. After his one-and-a-half-season stint sitting on the bench of The People’s Court ended in March 2001, he spent a lot of time at home “licking his wounds,” the source tells In Touch, while “Judy flew off to LA every other week to tape [ her show].” Jerry found comfort with Kary, and they became intimate a year later, carrying on the affair inside the $11 million Naples, Fla., condo that Jerry shared with his wife (see sidebar). According to the source, Jerry even professed his love to Kary and talked about marrying her, buying them a million-dollar apartment and giving her a restaurant of her own. Then pictures emerged of Jerry and Kary together, and Judy learned the truth.
Jerry’s cheating left Judy so angry, she came close to leaving him again. “She practically had Jerry’s bags packed and at the door,” says the source. “Judy lost something in her marriage to Jerry. He created a fracture that has never truly healed.”
That old drama could have a devastating effect on the marriage even now. “If the hurt is deep, then no matter how much time passes, it’s still there,” explains Beverly Hills psychologist Julie Armstrong, who hasn’t counseled the Sheindlins. “And if you bring it up, it’s painful. It can reemerge if the person felt particularly wounded or particularly hurt.”
Judy speaks her mind freely on her show, but she’s been less than willing to talk about what happened with her husband. She tried to brush it off when Larry King asked during a 2002 interview about headlines touting the affair. “Why in the world would I comment on something that is so stupid and hurtful?... All I can tell you is, would he be a real idiot to risk everything that he has?” Pressed, Judy cryptically added, “The only thing I can tell you is I didn’t fool around. I don’t have a boyfriend. That I can tell you for sure, for certain.”
She ultimately made the difficult decision to stay married and not live without her husband again. In her 1999 book, Judy discussed what happened after she briefly divorced Jerry in 1990 following a period of emotional upheaval related to the unexpected death of her beloved father. “I realized that I could get along just fine on my own. The question was, did I want to?” she wrote, later adding, “You have to do what makes you happy, but I learned the hard way that sometimes what you think will make you happy won’t. You have to step back from your emotions and decide what matters most.”
Judge Judy doesn’t give up on anything easily, but she’s given up on her marriage before — and she could do it again. “Her marriage is really at a crossroads. But for Judy, more than ever, it’s ‘my way or the highway’ when it comes to dealing with Jerry,” explains the insider. As anyone who watches her show knows, “Judy is forceful and decisive, and if she sees her marriage going south, she won’t hesitate for a moment to pull the plug,” adds the friend. “She and Jerry have had some wonderful times in their marriage, especially with their kids’ marriages and welcoming their grandchildren into the world, but that might not be enough.” ◼
Jerry’s always been the first to admit Judy wears the pants in the family”
— A FRIEND