• Judge Judy takes on a different role once she’s off the job.
  • She married the same man twice.
  • She raised five kids and is a proud grandmother of 13 grandchildren. She officiated her first grandson’s wedding.

Judy Sheindlin, better known as “Judge Judy,” is well aware that she is a demanding TV host and that someone else will probably take her place as America’s most popular TV judge at some point.

Judy discussed this in a conversation with Larry King in December of 2006. She did mention, however, that she did not wish for her position on the “Judge Judy” program to be filled by another person.

“I don’t know if I want anybody to replace me in my chair. I know somebody will come along. “They will find somebody feisty and tough,” the TV star said.

After 25 seasons, Judy’s courtroom reality program was canceled in 2021. Consequently, she could walk away with an income of $440 million.

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According to reports, the media personality has raked in an average of $47 million annually while working as a host on the TV program since 2012. This places her among the highest-paid television hosts. She made a joke about her high salary in 2017, saying,

“I joke now. I certainly don’t want pay parity with guys.”

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Off-screen, Judy has a different personality, including the roles of mother, wife, and grandmother. It was reported that she did not appear to be the same person when she went public with her devoted husband, Jerry Sheindlin, in November 2022.

She was tanned and dressed casually for the couple’s lunch date, which was very different from her early years on TV when she wore formal courtroom clothes when she was on the show.

In addition, Judy once explained that after a hard day at work, she would go home and prepare meals for her family, in addition to  “appointments, clothes, socks – and not everybody is as neat as you would want them!” continued.

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Judy has shared private information about her work with her fans for her career. She shared images of herself acting in activities at home between March and April 2020.

In one picture, she was playing Scrabble, and in another, she was shown to be running. She wrote, “Exercise is important. However, remember to practice social distancing!”

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Judy has always had a soft spot in her heart for critters. She posted a picture of herself and her dog, Scout, on social media, having “lunch” outside the house. She captioned the photo of herself with the phrase, “Spending valuable time with my favorite dog!”

The woman, born and raised in New York, also shared a photo of herself grinning for the camera while working her cooking magic in the kitchen. She confessed in the caption that she hadn’t cooked in a long time.

Judy had three weddings, but she married the same man twice.

Judy has been married twice in her life to the same guy. All three of her marriages ended in divorce. In 1964, the author wed her first husband, Ronald Levy, a prosecutor.

After getting married and relocating to New York together, the couple quickly became parents of their two children, a boy named Adam and a daughter named Jamie.

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In an interview from 2017, Judy discussed her first marriage, during which she revealed that, despite her first husband being a decent individual, she and her first husband resented each other.

She stated that she did feel pressure during those times to become a family woman. And she had already given birth to a child before she turned 21, and all her friends were getting married around the same time.

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Despite this, she ended up divorcing the person who was the father of her children in 1976, after the couple had been married for a total of 12 years. The following year, in 1978, Judy tied the knot with Jerry, another lawyer who was already a parent to three kids.

Their relationship reached a breaking point when she lost her father in 1990. In those days, Judy seemingly did not appreciate that her partner did not try to comfort her when she was sad, and she threatened to end their marriage. It was a challenge for him, and she accepted it. Jerry reflected on the unexpected event that occurred in May 2020:

“She said, ‘If you can’t maneuver this, I will divorce you.’ And I said, ‘Oh yeah? I dare you.’ And the next day, I got divorce papers.”

Even though this happened, the two sweethearts got back together a year later and got married again in 1991. They have been married ever since. The couple has since relocated to Florida with their three dog companions.

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Judy pointed out in her work “What Makes a Marriage Last” that men and women are wired differently. In addition, she bolstered the relevance of her claim by stating.

“Women will accommodate men from the beginning, and after they get married, they say, ‘All right, you start accommodating me. You start changing.'”

In her book, Judy also addressed some things couples should and should not do “What Would Judy Say? A Grown-up Guide to Living Together with Benefits.”  She stated that she has nothing against people who choose to cohabit before getting married, but only if they have a plan for how they would go about it.

According to the TV producer, the most important rule for that arrangement was that it would only last for a certain amount of time. Second, she recommended that married partners maintain their property rights.


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Judy added that women should prevent getting pregnant before marriage. She said, “I’m old fashioned in that respect,” and added that it was all from experience:

“I would say it’s wise, live together, give it the old college try, and move on if it doesn’t work. And if it does, get married.”

Judy’s Five Adult Kids

Judge Judy gave birth to her first child, Jamie, in 1966, and a few years later, in 1968, she received her second child, Adam. She has never considered the decision to put her career on hold to raise them.

However, the Emmy Award winner suffered from boredom while caring for her children at home. Judy decided to get her Master’s in Family Law from New York University and return to school.

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Five years later, the philanthropist also decided it was time to go back to work; however, her then-husband was against the idea, which finally led to the breakup of their marriage. As a couple, they, too, started falling apart over time.

Concerning the couple’s children, their daughter decided not to become a lawyer and has stayed out of the public eye ever since. On the other hand, one cannot say the same thing about Judy and Ronald’s only child, Adam, who continued in their parent’s footsteps. Adam’s career as a lawyer began when he was appointed District Attorney (D.A.) in Putnam County, New York.

Unlike his older sister, Adam became famous in 2013 when he sued Putnam County Sheriff Donald Smith for $5 million for defamation. The proceedings lasted for a total of four years, and Adam won that battle in the end. The court ordered Smith to pay him $150,000 and apologize to the public for his actions.

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During this time, Judy’s two stepkids, Gregory and Nicole, decided to pursue legal professions. Gregory was the first to graduate from Brooklyn Law School with a Doctor of Law (JD) in 1989.

Gregory began his legal employment as an Assistant District Attorney at the Office of the District Attorney for New York County. After that, he worked as a trial attorney for four years. He joined Sheindlin & Sullivan, LLP as an associate before deciding to launch the Sheindlin Law Firm in 2014.

In the same spirit as his stepbrother Adam, he has also been involved in his fair share of high-profile court dramas. Gregory took over the case in 2009 after a man named James H. Brady failed to pay his rent in Manhattan, and Gregory represented the commercial landlord pursuing Brady in court.

Jerry Sheindlin with his wife, Judge Judy Sheindlin and son Adam Levy on January 23, 2007┃Source: Getty Images

Jerry Sheindlin with his wife, Judge Judy Sheindlin, and son Adam Levy on January 23, 2007┃Source: Getty Images

Brady was found guilty, but years later, he tried to get the decision overturned by filing lawsuits. He filed a lawsuit against several defendants, including Gregory, and asserted that the decision was falsified to take away millions of dollars from him. He was required to pay a total of $1.7 million.

Nicole, Gregory’s sister, began her academic career at the University of Buffalo, where she earned a Bachelor of Arts degree in Design and Applied Arts. In 1993, she graduated from New York Law School with a Doctor of Law (JD).

Nicole began her legal practice as a Senior Attorney in The Legal Aid Society’s Criminal Defense Division. However, she decided to part ways with the business in 2007 to concentrate on building her private business, Mentzer & Sheindlin. Nicole is a passionate explorer who has visited a total of 38 countries. She also established a mentoring program.

Jonathan is the only family member with a different profession than his parents and brothers. He attended New York Medical College to earn his medical degree (MD) and did his ophthalmology internship at St. Luke’s/Roosevelt Hospital Center.

Judy Sheindlin with her husband Jerry Sheindlin and their daughter Nicole Sheindlin arriving at the Women's Guild Cedars-Sinai's Annual Luncheon at the Regent Beverly Wilshire Hotel on April 13, 2015 in Beverly Hills, California ┃Source: Getty Images

Judy Sheindlin with her husband Jerry Sheindlin and their daughter Nicole Sheindlin arriving at the Women’s Guild Cedars-Sinai’s Annual Luncheon at the Regent Beverly Wilshire Hotel on April 13, 2015, in Beverly Hills, California ┃Source: Getty Images

Judy and Jerry were blessed with grandchildren after raising children who had successful careers. When discussing the couple’s first granddaughter, the doting grandmother became emotional as she recalled the first time she saw him on the day he was born:

“[..] I looked at him and thought he was the most spectacular baby I had ever seen. [..] There’s something different about our first grandchild.”


Meanwhile, doting grandfather Jerry reflected on their memories of their grandson and revealed that they were obsessed with him.

“[..] We kind of stole him right after he was born, and I used to carry him around, and people used to say, ‘Oh, what a handsome son you have,’ and I would say, ‘Thank you.’ I never said he was my grandson, so it was fun.”

Judy Presided Over Her First Grandchild’s Wedding

When Jerry’s wife was requested to officiate at the wedding of their oldest grandchild, Casey Barber, who was marrying Olivia Weil, she felt even more honored than she already did. Both newlyweds are lawyers, and they first met in law school.

Casey and Olivia were married in a lavish wedding celebration on Judy’s estate in Greenwich, Connecticut, in September 2013. There were 150 people in attendance at the wedding ceremony and reception. Sheindlin

Of the television star’s granddaughters, her grandson Barber and her granddaughter Sarah Rose are lawyers.

They not only follow in her footsteps, but they also appear like her. Judy shared a throwback photo of herself in January 2018 with the caption, “#TBT Judge Sheindlin growing up as a young girl in Brooklyn!” The photo revealed Judy’s uncanny resemblance to her grandchildren.

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Judy has thirteen grandchildren, aged from under ten to the late thirties. Although she is best known for her toughness and her “no-nonsense” approach in the courtroom, she has confessed to being a softie when it comes to her grandchildren:

“I spoil them. I’m trying to think of how we don’t, but the answer is we do.”

However, that does not completely rule out the possibility that she is being severe with them. Sarah, one of her grandchildren, disclosed that their grandmother exercises a strict parenting style at home.

“That’s still there. The no-nonsense grandmother is still there. But there is a much softer, supportive side.”


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Sarah said she calls her grandmother Judy first whenever she has a problem or needs a problem solver. This is because Judy is very good at finding solutions to problems.

In addition, she disclosed that her family is full of lawyers who discuss various aspects of the law while they are eating supper together. Sarah mentioned that she always had the impression that she was being excluded from the discussions that her aunts and brothers used to have at the dinner table when she was a child and that she hoped to be able to join in those discussions in the future.

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Because of this, she, too, decided to pursue a profession in law and, ultimately, taught herself how to “communicate and think like a lawyer.” She was grateful that this enabled her to communicate with her loved ones at home and expressed her appreciation for having this capability.

During her commencement speech at New York Law School, Sarah was honored to have her renowned and much-loved grandmother present her with her diploma. Sarah felt extremely privileged to have this experience. During an interview in 2022, she expressed gratitude toward Judy for her influence on her life.

“[She taught me] not to let anybody else define you but yourself. [..] She’s given me the confidence to feel that way while I was growing up. I think that’s the best advice she’s ever given me.”

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Sarah, who has always referred to Judy as “Nana,” wrote a touching tribute for her in November 2021. She recalled how she and her siblings, cousins, aunts, and uncles would get together at her lake house every weekend when she was a child, and she said that it was one of her happiest recollections.

“[…] The home videos of everyone laughing, bundled up, and spending time together show how precious family is. You’ve always told me, ‘If you set the table, they will come,'” Sarah wrote, adding:

“You have set the table for decades, and we all continue to gather there.”

She stressed the importance of family and said she witnessed “first-hand how amazing it can be when there is a strong matriarch leading the way.”

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Sarah completed her heartfelt tribute to her devoted grandmother by expressing her gratitude for the role that her grandmother plays in her life as her “biggest cheerleader and supporter – and very best friend.”

After the conclusion of the long-running “Judge Judy” show, Judy made her glorious return to the small screen alongside her mentee granddaughter Sarah in the spin-off program “Judy Justice,” in which Sarah plays the role of a law clerk.

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