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In Judy We Trust

Judge Judith Sheindlin found fame and fortune in an offbeat TV courtroom—but the private star’s rise is similarly unconventional

Judy Sheindlin shuffles a deck of cards like she’s mad at it. We’re in her dressing room at Sunset Bronson Studios in Hollywood, where she’s taped her popular courtroom show for nearly two decades. Judge Judy is the most-watched daytime program on television, averaging about 9 million viewers daily. The show often beat Oprah Winfrey’s final season in the ratings and reportedly earns CBS more than $200 million every year.

This money is not spent on the dressing room, which looks like a suite at a Holiday Inn. The lighting is less than flattering. And there’s a sitting area with nondescript furniture where, between cases, Sheindlin, 70, plays hands of gin rummy to keep her energy up. “My maternal grandmother taught me to play,” she says, barely looking up as she shuffles. “She didn’t let me win. And I don’t let my grandchildren win!” Sheindlin doesn’t let her staff win, either. One longtime employee has been playing gin with Sheindlin for years and says, “She’s happy to take my money.”

Not that Sheindlin needs it. In April, she extended her contract through 2017, adding an additional two years and $90 million. She is the highest-paid person in daytime television. She works exactly 52 days a year. It appears she’s worth it. While most other courtroom shows on television—such as The People’s Court and the now-canceled Judge Joe Brown—took a ratings hit in 2013, Judge Judy held firm. The program finally won a Daytime Emmy this year, after 14 consecutive losses. How was the ceremony? “I haven’t gone for years,” Sheindlin says, smiling. “I like to watch it from my bedroom.” Which one?

Judge Judy has made Sheindlin a very wealthy woman, with a family spread in Wyoming and homes in Los Angeles and Naples, Florida, not to mention a 20,000-square-foot colossus in Greenwich, Connecticut—complete with eight bedrooms and 10 marble fireplaces. She is said to have paid $13.2 million for the estate in 2007 and promptly demolished the existing residence, re-building from scratch. (Her property taxes alone are $230,000 per year.) In June, Sheindlin was spotted driving a Bentley convertible around Greenwich. When asked about the car, she downplays the extravagance, saying: “It’s an old Bentley.” Besides, she says, she prefers her Lexus wagon.

In a testament to her iconic status, earlier this year Reader’s Digest named Sheindlin one of the most trusted people in America, behind Tom Hanks and Sandra Bullock. Jimmy Kimmel, in a recurring segment called “Lie Witness News,” announced that President Obama had just appointed Judge Judy to the Supreme Court. One viewer apparently agreed with Obama, lovingly describing Judge Judy as “gangsta.” Sheindlin got a kick out of the segment and called Kimmel herself to say so. “Being called gangster was a first for me,” she says.

If there’s something gangster about Sheindlin—and no one doubts there is—it may be her bling. While she shuffles the cards, one can’t help but notice the emerald-cut, Kardashian-size diamond ring she wears. “I didn’t get a ring when I became engaged,” she says. “I got one later in life. I bought a smaller one when I first started [the show]. My husband said, ‘Really, you need a bigger one.’ He bought it for me for a birthday.”

Judge Judy Sheindlin (right) with her husband Jerry Sheindlin. Photo: Marcel Thomas/FilmMagic

 Twice a month, Judy Sheindlin travels to Los Angeles for two to three days of filming. In that time, she’ll preside over 20 or 30 cases—real cases, researched and recruited by a team of more than 60 scattered across the country. The participants are flown to L.A., where they agree to binding arbitration. (The cases cannot exceed $5,000.) Nothing is scripted. Not even Sheindlin’s enviable one-liners. At this point, she says, “It’s second nature.” I am about to find this out for myself.

It’s the end of June when I meet Sheindlin in the lobby of the Montage, a residence hotel in Beverly Hills, where she recently closed on a condo that cost a reported $10.7 million. After years of staying in hotels—first the Peninsula, then the Beverly Wilshire, made famous in Pretty Woman—she decided to put down roots. Why now? “Because we could.” OK, but $10.7 million? “All the kids were taken care of and the grandchildren are taken care of. It’s like a hotel, but we don’t have to move our stuff.” It’s worth noting Oprah is said to also have an apartment in the building, though they’ve yet to run into each other. That’d be fun, I say. “Sure,” she says, not wanting to engage.

Sheindlin, wearing a navy suit jacket and slim black pants, is just over five feet tall and toned. Last year, around her 70th birthday, she went on Katie Couric’s show and debuted a recent photo of herself in a white bathing suit. When I compliment her, she says: “It was incredibly smart of me to put on a cover-up.” Shifting uncomfortably in her chair, she reaches for a small silver key chain. Sheindlin suffers some lingering pain from a past back surgery, and she hopes an Aleve will do the trick. She notices me noticing her stylish undercover pill case.

“Florida,” she says, by way of explanation. “In Florida we have more pill holders than any place else in the world. We don’t have a big selection of condoms! We have a big selection of pill holders.” She takes a sip of water. “OK. Let’s go!”

She’s been impatient from the start. The facts of the case: Born Judith Blum in Brooklyn, New York, in 1942 to Murray, a dentist, and Ethel, a homemaker. “Luxury was going to the Catskills,” Sheindlin says, “and taking two cha-cha lessons with the dance instructor in a weekend instead of one.” They were comfortable, not to mention progressive. Sheindlin’s father encouraged her to pursue an advanced degree; just as important, he taught her comedic timing.

While still in law school, she married Ronald Levy, a lawyer, in 1964. Her first job, at a cosmetics company, didn’t take. Neither did her first marriage. Her husband treated her career as “something to keep me busy—like bridge,” she has said. They had two kids together, but after 12 years of marriage they called it quits. Three weeks later she met Jerry Sheindlin, a criminal-defense lawyer, at a bar. In one of many apocryphal stories about Judge Judy that turn out to be true, she walked up to him at the bar, put her finger in his face, and said, “And who is this?” He replied: “Lady, get your finger out of my face.” They began dating, and when he wouldn’t commit to marriage, she pulled out her datebook and cornered him. “I did propose to him,” she says now. “I said to him, ‘Where is this relationship going?’ And he tried to weasel out of it, with his, ‘Well, you know, why do we have to get married?’ Whatever. He finally capitulated. I told him to pick a date. He picked Flag Day.” The two married in 1978; between them, they have five children.

If that had been the end of the story, Sheindlin says it would have been enough. In 1993, she was working in family court, making $113,000 a year. She ate Egg McMuffins for breakfast every day: “I still think an Egg McMuffin is the best breakfast.” She drove a Nissan Maxima to work. “We’d get a new Maxima every four or five years,” she says, “and we had an old second car.” As a judge in family court, the mandatory retirement age is 70. “My husband and I had envisioned a very pleasant retirement with two small pensions, some Social Security and a small apartment a couple of blocks off the beach in Florida. I would have been very happy.” Here is the rare moment she pauses to smile. “But this certainly was a more interesting adventure,” she says.

Sheindlin on set in 1995. Photo: Getty

How does a New York City family-court judge, in pre-Internet days, wind up with a national television show? Start by having a big mouth. Ed Koch appointed Sheindlin to the bench in 1982, where she quickly earned a reputation for, well, basically what you see on TV every day. Catchphrases like “Sir, has anyone told you the story about Pinocchio?” started here. Custody fights, 10-year-olds committing assault, family dysfunction: Those were the story lines that played out in her courtroom, and Sheindlin was far from sympathetic, making enemies of lawyers, often by cutting them off. The system was overcrowded, and there simply wasn’t time for hand-holding. In 10 years, she presided over something like 20,000 cases. Her no-nonsense approach led to a profile in the Los Angeles Times, as part of a series on social innovators. To be clear, Sheindlin wasn’t looking for publicity—not for herself, anyway. She was looking to expose the cracks in the system. “Family court was sort of a dumping ground for bad, bad judges—because it was closed to the public,” she says. “If you wanted to hide somebody—if you owed somebody a favor and wanted to hide them—family court was the place.” She was happy to let a little light in.

The Los Angeles Times piece—featuring Sheindlin zingers like “I can’t stand stupid, and I can’t stand slow” and “I want first-time offenders to think of their appearance in my courtroom as the second-worst experience of their lives…circumcision being the first”—led to a 60 Minutes segment. (She’s still opinionated. Her views on gay marriage: “I’ve always felt the same way about Americans who work and pay taxes. And do the right thing. Why do we care about this? It should be a non-issue. It’s a non-issue.”) Then Hollywood showed up.

After 17 years on air, when Sheindlin catches a rerun from the early days of Judge Judy, she’s critical, though not for the reasons you might think. “I say to myself, ‘You know, you should have let somebody else do your hair.’ I did it at the beginning. They used to call me the Kitchen Beautician. I went to the drugstore and got some wash-in color. I didn’t think it mattered. Truth is, it does matter.”

Despite her lifestyle and earning power—she tied Katy Perry on Forbes‘s 2012 list of highest-paid women in Hollywood—Sheindlin seems intent on holding firm to her Brooklyn roots. I ask about another of those apocryphal stories—that her 20,000-square-foot home in Connecticut was built in only three months, with construction workers toiling around the clock, seven days a week. “That’s not true,” Sheindlin sniffs. “It was built in short order,” she says, pointedly, “in less than a year. But that’s not true.” Still, how’d it go up so quickly? “You have to be able to say, You know what? That color marble isn’t so important. If you can’t get this one, get something that’s close. You can’t get that wallpaper, get something close. You have to be flexible if you want to get in and enjoy it.” Seriously, that’s it? The estate has gold-plated fixtures and what’s been called a mile of paved walkways. Sheindlin will concede: “When we drive through the gates to get to the house, there’s something almost fairy-tale about it. All from a little TV show.”

The high life hasn’t much changed Sheindlin, says longtime friend and gossip columnist Cindy Adams. “Judy is very easy; she had it a hundred years before everything hit for her, so she knows what it’s like to be a normal, regular person,” says Adams, who was introduced to Sheindlin when their shared banker recommended the judge offer her advice on training Adams’ ungovernable Yorkies. “Maybe she wears better shoes now. Or better clothes. But nothing else has changed.”

This fall, the 18th season of Judge Judy begins airing. What’s more impressive than her schedule (52 days a year! $45 million salary!) is that she’s negotiated it all without an agent. Of her schedule, she says: “It’s not something I like to talk about. We tape 50 days a year. That doesn’t mean that’s all you work.” But she is more direct on the topic of representation: “Nobody understands your own worth more than you do,” she says. By the time her contract expires in 2017, she will be 75 years old. It may sound like a nice round number. But her longtime producer, Randy Douthit, can’t imagine Sheindlin walking away, even then. Yes, the travel will take a toll as she continues to age. She has to fly to L.A. twice a month. “In her private jet,” he adds, with a smile.

Sheindlin has flown private since just after 9/11. “If I’m going to continue to work,” she says, “I really have to make it easy for me to get to and fro.” She lives in Florida from October through May and spends the rest of the year in Greenwich. The family bought the place in Wyoming in 2011 so the kids could ski. On the private jet, Sheindlin preps her cases, then reads the New York Post, the Financial Times, USA Today, and the New York Times, usually in that order. “The plane has WiFi, so I catch-up on e-mails.” Has she read any good books lately? “My own!” she says. (Her sixth book, What Would Judy Say?, was published in April.) Her husband, the retired judge Jerry Sheindlin, accompanies her, making good use of the Montage’s gym. (“He’s buff,” Judy says.) They fall asleep at night watching reruns of Criminal Minds. “I don’t like to leave things hanging,” she says. “I’m not saying in the morning, What did I miss? I’ve seen it before.”

Do she and her husband argue? “All the time,” Sheindlin says. About what? “Everything. Nothing that I’m going to discuss with you.” Shifting in her seat, she issues her verdict: “Are we almost finished? I’m exhausted.”

OK. Last question: What does the staff on the private jet call you? Mrs. Sheindlin? Judge Judy? She smiles, finally: “To my face or behind my back?”


Sheindlin is perched on her stand, presiding over a landlord-tenant dispute—her fourth or fifth case this morning. In person, the “courtroom” appears as you’d expect: It’s like the set for a community production of 12 Angry Men, populated by “extras” who—while Sheindlin is backstage playing hands of gin—argue amongst themselves about the verdicts and the judge’s awesomely personal barbs.

The case we’ve just seen concerns a 39-year-old tattoo artist and his 23-year-old girlfriend who rent a one-room bungalow in Los Angeles, for which they pay $765 a month. Or at least that’s what they’re supposed to pay. They haven’t written a rent check in months, citing rodents, mold and a disagreement over the electricity bill as reasons to shirk. Sheindlin has little patience for them, or most other litigants. If the disputes are mundane and the litigants less than charismatic, no worries. Sheindlin’s skill is in the well-timed personal attack. Viewers love to see her put deadbeats in their place.

Nearing a verdict, Sheindlin says: “You don’t have a lease. You’re not trapped. You’re not happy? Move. Move!” The man backpedals, but Sheindlin puts it in terms he can understand, accusing him of going out for a steak dinner and not paying the bill. “You want to live with a 23-year-old who doesn’t work?” she says, smelling blood. “That’s your prerogative. You ate the steak. You have to pay.” Next!

There’s a second case—a dispute between two sisters. When one sister had her car repossessed, the other sent her a $1,600 Walmart MoneyGram. Was that a gift? Or a loan? (Sheindlin’s verdict: Pay it back!) Then one about a young man from Atlanta driving an uninsured car. The cases are entertaining enough. But Walmart MoneyGrams? Disagreements over $765 studio apartments? This is more Kitchen Beautician than Greenwich millionaire. When she’s back in her dressing room playing cards, I can’t help but wonder if Sheindlin can still relate to her constituents. “I understand the question,” she says. “But I don’t like the direction!” Then she lets out a very large laugh.

Sheindlin will make nearly $1 million today—or, roughly $100,000 per verdict. Nice work, if you can get it. But at age 70, wouldn’t she rather be kicking back? “I still love to go to work every day,” Sheindlin says, turning it on us: “Don’t you?”



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