Inside the Winning Love Story of Judge Judy and Husband Jerry Sheindlin

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Sarah Grossbart
·11 min read
Inside the Winning Love Story of Judge Judy and Husband Jerry Sheindlin
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Let the record state that Judge Judy Sheindlin and her husband, the honorable Jerry Sheindlin, haven't had the most perfect of marriages. But we're going to go ahead and deliver our verdict: Anyone who makes it past their silver anniversary is a winner.

And Judy is already well into her 44th year of marriage with Jerry, which is some two decades longer than she's presided over her triple Daytime Emmy-winning eponymous court series Judge Judy—one of the longest-running shows on television with ratings that far surpass pretty much anything else that airs during your lunch break.

The pair just had to overcome one teeny, tiny blip that saw the two judges, perhaps ironically, facing off in court.

Dissatisfied with Jerry's inability to take care of her as she grieved the 1990 death of her father, Judy issued an ultimatum. "She said to me, 'If you can't maneuver this, I'm going to divorce you,'" he recalled to Marlo Thomas and Phil Donahue in the duo's May 2020 release, What Makes a Marriage Last. "And I said, 'Oh, yeah? I dare you.' And the next day I got divorce papers. The next day. So, that was the end of that."

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It wasn't of course, their split lasting all of a year and ending with Judy accepting this particular blindspot of her husband's, declaring to Marlo and Phil that oftentimes you truly can't change a man: "Like they say, don't try to teach a pig to sing. It doesn't work and it just annoys the pig."

Not that Jerry, a retired New York Supreme Court justice, regularly gets a pass. In real life, Judy is every bit the exasperated, watch-tapping, meme-generating, take-no-prisoners cultural icon that she portrays onscreen, never afraid to unleash one of her patented insults or remind a defendant, "On your best day, you're not as smart as I am on my worst day." (Or, as Amy Poehler lovingly referred to her as she presented Judy with her lifetime achievement Emmy, "the Jewish mother we all want.")

Curb Your Enthusiasm Guest Stars, Judge Judy
Curb Your Enthusiasm Guest Stars, Judge Judy

She split with her first husband, fellow prosecutor Ronald Levy, after 12 years and two kids—daughter Jamie Hartwright, born in 1966, and Adam Levy, born in 1968—because, as she put it on the Fox News show, OBJECTified, he saw her career in law "as a hobby." Entering back into the workforce, she was a prosecutor in the New York family courts when she first cross-examined defense attorney Jerry in a bar.

"I just finished trying a murder case as a defense lawyer," he recalled to the Los Angeles Times years later in 1999. "There was a reporter from the New York Post there at the bar, and I was speaking to him about the case. Judy came walking in and put her finger in my face and said, 'And who is this?' I said, 'Lady, get your finger out of my face.' We've been together ever since."

Transitioning from his work on the New York Supreme Court at the time, Jerry was speaking to the paper about his new gig as arbitrator on the third season of The People's Court—a role that his bride pushed him to consider despite it placing him as her direct competition.

"She is the one that told me I should do it," he assured in that 1999 interview. "If she had any reservations at all, I wouldn't have done it."

Not that she had allll that much to worry about considering Judge Judy began crushing its next closest competitor, Oprah Winfrey with all of her free cars and celebrity confessionals, two years after its 1996 debut. Still, Jerry cautioned to the paper, if "my show takes off and I beat her, I am contacting Hollywood immediately to remake the movie Sleeping With the Enemy."

One could argue a ratings battle was nothing compared to what they'd already endured.

Judge Judy, Late Night With Seth Meyers
Judge Judy, Late Night With Seth Meyers

Having spent the first decade-plus of her marriage tending to Jerry's needs while also building a legal career that had taken her from prosecutor to judge, Judy was thrown when her father ("My champion" she she put it to Thomas and Donahue) passed away in 1990.

In desperate need of a role reversal, "I said, 'I've been taking care of you for 12 years, now it's your turn to take care of me.' And he was totally unaccustomed to that role," Judy detailed of her husband in What Makes a Marriage Last. "I wasn't asking for anything unreasonable, and he wasn't being unreasonable saying that he really didn't know how to do that. He was 55 and had lived a certain way all his life. He couldn't even conceptualize taking over that role. He just couldn't."

Agreed Jerry, "What she said was, 'Unless you change, we can't stay together.' I said, 'Tell me what you want me to do. You can't just say 'take care of me.'' What does that mean? Do you want me to carry you from place to place? Do you want me to buy you things? Do you want me to feed you? Do you want me to keep you warm? What you have to do is tell me—use your words and tell me what you want me to do to take care of you.' She said, 'Just take care of me.' And I said, 'I don't know how to do that.'"

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The stand-off led to the sort of expedited divorce that occurs when both halves of the couple are judges. Then, not long after, came the regrets.

"I missed her presence the very first week that we were separated," he shared. "It was the first time in years that we didn't get to see each other every single day. It was such a strange experience."

Equally as forlorn, she was receptive when he phoned her up after a year apart, agreeing to his request for dinner and gamely detailing one particularly unsuccessful date that had her telling an overweight suitor to rethink his dinner order. "I was so pleased having her tell me that story," Jerry said, "because, at that moment, I knew she eventually had to come back to me."

Judge Judy, Judy Sheindlin
Judge Judy, Judy Sheindlin

Both in agreement that the previous year without each other had been rough—"I missed him," allowed Judy—they decided to give both their romance and matrimony another shot.

"I like being married," Judy noted of their decision to retie the knot. Ahead of their first vows in 1977, she recalled in the book, "I actually had to drag him to the altar....He had no intention of divorcing his wife, even though they had been separated for three or four years. After we were together for about a year, I said, 'I want to see your divorce in the newspaper or don't bother calling again.'"

When he argued they could simply live together, Judy countered it'd be his job to inform her father. "I said, 'I'm not going to do that,'" recalled Jerry. "So she whipped out a calendar and said, 'Pick a date. Now.'"

This time around, though, he was the one tossing out propositions. "I picked her up from work at family court one day, and we were walking through downtown Manhattan," Jerry shared. "Suddenly I said to her, 'This is silly. I'm uncomfortable being with you all the time and not being married to you. Let's get married again.' She said, 'Well, how are we going to do that?' I said, 'The clerk's office is right up the street. We can go in and get a license…'"

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As predicted, their marriage license request was handled immediately, the standard 24-hour waiting period waived. The pieces snapping into place, she called up her best friend of 40 years to serve as maid of honor, he contacted his son, working at his downtown Manhattan law practice to stand in as best man, and after a quick call to Jerry's New York Supreme Court justice pal they had an officiant.

"So we go up to Herbie's chambers, and he performs the following ceremony," Jerry recalled. "To me he says, 'Do you take this woman to be your lawfully wedded wife forever—in good times and bad, in sickness and in health?' I said, 'Yes.' He looks at Judy and says, 'Do you take this man to be your husband?' She says, 'Yes.' He says, 'In good times or bad?' And she looks right at him and says, 'In good times or forget it.'"

Judge Judy, Jerry Sheindlin
Judge Judy, Jerry Sheindlin

In the three decades since, they haven't had to put those vows to the test.

A 1993 Los Angeles Times profile on Judy spiraled into a spot on 60 Minutes, then her first of seven books, 1996's Don't Pee on My Leg and Tell Me It's Raining and finally reality TV stardom. Her net worth estimated at roughly $440 million, their life together includes multi-million dollar spreads in Beverly Hills (a five-bedroom condo her landing spot when she films Judge Judy), in Greenwich, Conn. (a sprawling 12.5-acre spot some 35 miles outside where they both grew up in New York City) and their home base: a massive compound in Naples, Fla., where Judy spends several mornings at the Ritz-Carlton, Jerry joining her for lunch.

Their five kids—Jamie and Adam from her first marriage; Gregory Sheindlin, 56, Jonathan Sheindlin, 53, and Nicole Sheindlin, 52, from his—have given them 13 grandchildren, at least four of whom are interested in the family business.

Judge Judy, Jerry Sheindlin
Judge Judy, Jerry Sheindlin

And having long eschewed retirement, Judy shows no signs of laying down her gavel. She expanded her television empire in 2014 to include Hot Bench, now the third-highest-rated syndicated show on daytime behind Dr. Phil and, well, Judge Judy, which she recently announced will end this year after 25 seasons. Though that's really only to make room for her latest venture, Judy Justice.

As for their union, though Jerry didn't magically transform himself into a doting caregiver during their year apart, "He did learn to use a calendar better," she remarked to Marlo. "He learned to write down: 'October 21, Judy's birthday. Buy present, card.'"

In 2019, to mark her 77th, he got her exactly what she wanted—more or less. "I said, 'I'd like a new Aston Martin,'" she detailed to the TMZ cameras waiting outside her Beverly Hills apartment. "And he said, 'What's your second choice?' So I got a bathrobe!" In Jerry's defense, he cut in, "It was from Aston Martin!"

Judge Judy Sheindlin, Judge Jerry Sheindlin
Judge Judy Sheindlin, Judge Jerry Sheindlin

That she finds the whole situation impossibly charming is evidence that you can learn quite a bit across four-plus decades of marriage.

"I believe that men's brains and women's brains are different," she explained in What Makes a Marriage Last. "Women will accommodate men from the beginning, and after they get married, they say, 'All right, you start accommodating me. You start changing.' I remember when one of our kids was getting married, she complained to me that her fiancé cleaned the bathroom with a sponge, then tried to clean the kitchen with the same sponge. She told me, 'I don't know if I can deal with this.' And I said, 'Sweetheart, this is as good as it gets. The truth is, you're not going to be able to modify that behavior, and if you're not prepared to live with that, then don't do it. Otherwise, buy a dozen sponges.' And they're still married, almost 25 years."

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In other words, that conventional wisdom about choosing your battles holds strong. Though Jerry would throw in an addendum that you also need to be certain you've found the person you'd like to fight alongside.

"The truth of the matter is: No matter how you slice it—no matter how many sponges you buy—it's all irrelevant unless there's a special feeling when you speak to her, when you hug her and tell her you can't do without her," he added. "If you love your mate, it all works out."

Judge Judy
Judge Judy

Which is something Judy has known at her core since the day she spotted Jerry at that New York bar.

Asked the advice she'd give any young couple standing before her bench, she informed Marlo, "I'd tell them they had to have that intangible feeling of looking across the room and saying, 'I've got to have me one of those.' My father once told me that the first time he saw my mother was at a dance at the Jewish center when she was just 18. She was so pretty. My father was with his best friend, and he looked at him and said, 'You see that pretty girl over there? I'm going to knock that halo off of her head.' And he did. But he loved her from the first minute he looked at her. He saw her and he said, 'I've got to have it.' That's how I felt when I saw Jerry. I said, 'I have to have that forever.'"

This story was originally published on Wednesday, Oct. 21, 2020 at 8 a.m. PT.