Arts & Entertainment

Judging Judy

What Judge Judy Sheindlin is like off the bench—and how she gets the most out of her life in Naples

BY September 30, 2014


It didn’t take long for Judy Sheindlin and her husband, Jerry, to make a home in Naples. In fact, it didn’t take long for them to make two.

It seems that when they bought their first place at the Carlysle at Bay Colony, the condo’s pet policy allowed only one dog per unit. So they did what any reasonable couple would do—they bought two residences at the Carlysle.

“Because we had two dogs. If you have two dogs you had to have two apartments,” Sheindlin says, with a laugh. “And then we realized how foolish that was and so we bought an apartment at the Windsor (at Bay Colony) where they ultimately did allow
 us to have both of our puppies [shih tzus Lulu and Honey, both of whom have since passed]. And we have been blissfully happy in Naples ever since.”

If you’re not familiar with Sheindlin, that black box in your living room is a television—turn it on.

Though she stands a mere 5 feet 1 inch tall, she is arguably the biggest television star in the country—perhaps the world. Sheindlin, best known simply 
as Judge Judy, is the star of the top-rated show in daytime television. And now, in its 19th season, Judge Judy has, like the woman herself, bucked tradition and actually gotten better over the years. In fact, her show has been ranked No. 1 for the past four seasons—which includes Oprah Winfrey’s final two years.

So just how did a family court judge from New York end up as one of TV’s biggest stars?

“I actually didn’t decide to do the TV show; somebody made the suggestion to me and I thought, ‘Hey, that’s a good idea,’” the 71-year-old Sheindlin says in her Brooklyn staccato. “You know, I was 
in the courts for a long time, and this opportunity came up to me when I was 51 years old and I thought it would be quite an adventure—a second career. A wonderful opportunity. You never know whether that works out or not, but I had my law degree and I knew that if it failed I’d always be able to make a living. And it worked out.”

That’s putting it mildly. The show filled a gap left by the departure of The People’s Court, and America fell in love with Sheindlin’s new brand of justice. Now, Judge Judy can be seen in 125 international markets and is watched by more than 10 million people a day in the United States. CBS, which owns the show, recently gave her a primetime special, signed her to another three years and green-lit a new syndicated show she created called Hot Bench, which will premiere this fall. A recent New York Times article estimated her yearly salary at $47 million for a 52-day shooting schedule. She even has a star on the Hollywood Walk of Fame.

Yes, things worked out all right.

“I must tell you I’m in the fortunate position of being able to make a living doing exactly what I’m most comfortable doing,” Sheindlin says. “So if somebody said to me, ‘Judy, you have to stifle the way you do your cases, we want you to be more like Joe Wapner—don’t get out there in their faces,’ I couldn’t do that.”

The fact is she resonates with viewers. So much
 so that a 2013 Reader’s Digest poll placed her among the “100 Most Trusted Americans.” And in this world of gridlock and political correctness, the author of such books as Don’t Pee on My Leg and Tell Me It’s Raining and Beauty Fades, Dumb Is Forever,
 is a breath of fresh air, even after 19 years. People crave plain speak and quick justice. And that’s exactly what Sheindlin delivers.

“I marvel at it,” says Charlie Henrich, vice president and general manager of Fox4, which airs four episodes of Judge Judy daily. “She calls the baby ‘ugly.’ And I think people appreciate that. It’s hard to find someone who cuts to the chase better than Judge Judy.”

“(People) like to see the good guys win and the bad guys lose and have justice move swiftly,” Sheindlin says. “Most people who’ve been involved in the justice system have found the experience totally unsatisfying … because it just works too slowly. That doesn’t mean that what I’m doing is a utopia or should be a template for how the court system should work, but certainly someplace in the middle of my lightning-speed justice and the molasses court systems that we have in most of the country. There has to be something in the middle of that.”

But her streamlined, justice-in-a-hurry approach is what helped get her to this place. Her family court career began back in 1972. At that time she prosecuted juvenile delinquent cases for the state of New York. But by 1982, then New York City Mayor Ed Koch appointed her to the bench. By 1986, she was the supervising judge in Manhattan’s Family Court. She retired from the bench in 1996 after hearing more than 20,000 cases. Justice, via the Sheindlin bench, was swift. Her speed, style and brashness garnered a lot of media attention.

But the career change to television star, and the freedom it delivered, gave Sheindlin and her husband—who was a justice on the New York State Supreme Court and presided over The People’s Court from 1999 to 2001—a lot of options. And one of those options was housing.

“I decided that the west coast of Florida was probably the most beautiful place that we visited. My husband and I spent some time in Sanibel and Captiva and we loved both. And when we first thought about having a second home, in Florida, the first place I looked was Captiva Island,” Sheindlin says. “It was the closest thing to the South Pacific that you could find. But I found that as magnificent as it was, there was only one way in and one way out. I said, ‘Well, that might lend to being a little frustrating.’ I figured that as long as I’m starting fresh, why start out with restrictions?”

So she reached out to her cousin, longtime Naples resident Bruce Sherman, who told her if she was going to live on Florida’s west coast, she had to come explore Naples. That was 1999. She and Jerry took a weekend and booked a stay at The Ritz-Carlton, Naples.

“We walked the beach and fell in love with each other again—and the beach,” Sheindlin says. “And we decided this would be the perfect place for us. As a matter of fact, that weekend, we bought our first apartment at the Carlysle. … And we knew it was the right place for us.”

Though they have other places scattered across the country (Greenwich, Connecticut; New York City; Jackson Hole, Wyoming, to name a few), the pair arrive in Naples in early October each year and stay through May. But during that stretch they also have to travel to Los Angeles every other week to film her show.

But once back in Naples, Sheindlin unplugs and rejuvenates with a schedule that she has fine-tuned.

“We have a wonderful
 routine of working out most
 of the morning and then we 
lunch,” Sheindlin says. “And 
then (we) usually have a little 
work to do to take care of the 
business of living. We are early 
diners so we eat early, watch
 a little TV (or) go to a movie,
 and go to bed. That’s it. That’s
 our time. We do not play golf.
 There are always chores to do.
 We’ve got a gaggle of grandchildren who are always celebrating a birthday or anniversary or a graduation or engagement. So there’s shopping and things.”

She also blended seamlessly into local philanthropy. When her good friend Denise Cobb asked her to help during the formative years of the Naples Winter Wine Festival, Sheindlin jumped right in. “Since our first festival, each year she has attended, made donations that raised hundreds of thousands of dollars with behind-the-scene visits to the Judge Judy set and lunches, and other personal things,” Cobb says. “She cooked breakfast for some winners, had a dinner party one year for another, etc., and she bids.” As a result, the board made her an honorary trustee a few years back.

And though she claims she and Jerry eat only at the same three restaurants over and over again (no, she wouldn’t say which three), her friends claim she loves trying new places. A notoriously healthy eater, she has a well-known diet cranberry juice fetish, and if the restaurant she’s dining at doesn’t happen to carry the beverage, she’ll ask the staff if they mind if she drinks her own, which miraculously appears from her purse.

But as much as she loves Naples, she’s not going to earn any points from the Chamber of Commerce when it comes to encouraging others to discover the area. She was recently a guest on The Queen Latifah Show and they discussed seeing each other at The Ritz-Carlton, Naples. But when asked if she mentions Naples to other celebrity friends, she’s quick to shut down that concept right away.

“The only other people we see here are the Philbins [Regis and Joy], who occasionally perform at (Artis—Naples). They’re friends of ours from Connecticut and New York, so when they’re here we see them,” Sheindlin says. “But the real answer is I don’t encourage anybody to come to Naples. I think it’s just fine the way it is. It has enough people.”

Of course, that doesn’t include family. A daughter and son-in-law and a brother and sister-in-law have places in Naples and tend to be her core circle when they’re in town. And the new people she does meet find a kinder and gentler Judge Judy than they might expect. Sheindlin talks more slowly and much more deliberately in person than she does from behind the bench.

“In my personal life I really try to be very careful not to offend,” says the mother of five, grandmother of 12. “If there are two or three ways to say something to somebody, including my own children, I try to pick the way that has the most honey on it. And I may try that with my litigants that I work with every day, but sometimes they’re so invested in their position that there is no getting through to them. So, just as when you talk to your own child, you say, ‘Listen, we’re not going to put our hand near that hot stove.’ And they look at you and they put their hand on the hot stove. And by that time, then you’re screaming at them, ‘Didn’t I tell you not to put your hand near that stove?’ Well, that’s what I do at work. I say, ‘You shouldn’t lend that bum money. And once you did, and he didn’t pay you back, you kept lending him and lending him money for the next four years, what are you coming to cry to me for?’”

It’s that ability to switch gears coupled with phenomenally broad appeal and deep pockets that make her the perfect consideration for political office. But when we asked her if she’d make a good politician, she had a quick answer.

“Terrible. I do not work and play well with others who have different agendas,” Sheindlin says. “Most politicians have agendas that are consistent with representing their constituencies. (Although) many forget who their constituencies are once they get to where they want to be. And I think that rule by committee is not consistent with my personality. All of those things. Plus, politicians can’t, by virtue of the way the system is structured, make any radical change quickly. There is no immediate gratification. There are always three or four sides. I really don’t need that. Why would I want to put myself in that position? When you really can’t make a meaningful change—even the politicians who are the most well-meaning find that at the end of the day they are frustrated. I’m never frustrated.”

Sheindlin tends to pick up steam when the conversation shifts to her passion, which right now seems to be travel. The Sheindlins recently purchased an apartment on the mega-cruise liner The World.

“It’s wonderful. It takes all of the stress and aggravation out of yacht ownership,” Sheindlin says. “It circumnavigates the globe every 12 months on a different route that’s selected by the owners. … We bought last October, so we’ve been to Venice and we did a short trip into Croatia, then we recently spent three weeks in New Zealand. Prior to that we were in Bora Bora and Moorea, in French Polynesia, the Canaries, Portugal and Japan, and we’re going to China in October.”

Just in time for her to return home to Naples with her current shih tzus, Diva and Bogey.


Telling a Good Judge from a Bad One

Judge Judy Sheindlin has created another syndicated legal television show called Hot Bench, which will premiere nationally this fall. Although it won’t feature her, it will include three judges who hear cases and argue its merits among themselves be- fore rendering a verdict. So we thought we’d ask her just what it takes to be a good judge.

“I think that a good judge knows that the first thing they have to do is to judge, which means you have to make a decision. And it has been my experience that judges, mostly because they don’t like to offend—but some don’t like to work hard, some of them don’t have the information, some of them don’t have the expertise—they would much prefer parties to civil litigation settle.

(Judges) will draw out a case, allow it to be drawn out, either until everybody gets financially tapped out or emotionally frustrated. And so the first thing you have to be when you’re a judge is be able to make a decision. Get the facts fast, as best as you can, and make a decision. If you take three and a half years to decide a custody case, that’s a big mistake. People are suffering while you are twiddling your thumbs. You don’t have to author a Brown v. Board of Education decision or an erudite decision in order to say, ‘The court awards custody to…’”


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