Judge Judy takes on a totally 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 grandkids. She officiated her first grandson’s wedding.
America’s beloved television arbitrator, Judy Sheindlin, better known as Judge Judy, understands that she is a hardcore TV host and that someone will take over the reins someday.
Judy said this in an interview with Larry King back in December 2006. However, she did note that she did not want a replacement for her position on the “Judge Judy” show.
“I don’t know if I want anybody to replace me in my chair. I know somebody will come along. They will find somebody who is feisty and tough,” the TV star said at the time.
Judy’s courtroom reality show ended in 2021 following 25 seasons. As a result, she walked away with a $440 million fortune.
The media personality reportedly raked in $47 million per year while on the TV show since 2012, making her one of the highest-paid television hosts. She quipped about her high salary in 2017:
“I joke now. I certainly don’t want pay parity with guys.”
Judy’s personality off-screen differs, including being a mother, a wife, and a grandparent. In November 2022, she stepped out with her beloved husband, Jerry Sheindlin, and reportedly looked unrecognizable.
She had a tan and opted for a casual look for the couple’s lunch date outing, which is the opposite of her early years in television in strict courtroom attire.
Moreover, Judy once explained that following a long day at work, she would go home and prepare meals for her family, “appointments, clothes, socks – and not everybody is as neat as you would want them!” she added.
Over the years, Judy has given fans a glimpse into her daily life. Between March and April 2020, she posted images of her participating in activities at home.
One photo showed her playing Scrabble, and another displayed her running. She wrote, “Exercise is important. However, remember to practice social distancing!”
Judy is an animal lover at heart. She shared a picture of her having “lunch” with her dog, Scout, outside her house. “Spending quality time with my favorite dog!” she captioned her post.
The New York native also posted a snap of herself cooking up a storm in the kitchen as she smiled at the camera. “Haven’t cooked in ages!” she admitted in her caption.
Judy Got Married Three Times—Twice to the Same Man
In her life, Judy has been married three times, twice to the same man. The author wed her first husband, prosecutor Ronald Levy in 1964.
The newlyweds soon welcomed two children, a son named Adam and a daughter named Jamie, after moving in together in New York.
Judy talked about her first marriage in a 2017 interview, and while she described her spouse as a good person, she also revealed there was resentment between them:
“My first husband is a lovely, lovely man, but he always viewed my job as a hobby and there came a time when I resented that.”
Judy also recalled that during those times, she felt pressured to become a family woman. Before turning 21, she already became a parent, “and all my friends were getting married,” she said.
Still, she and the father of her kids divorced in 1976 following 12 years of marriage. A year later, in 1977, Judy married Jerry, another lawyer, who already had three children.
Their union hit rock bottom in 1990 when she lost her father. Back then, Judy reportedly did not appreciate how her spouse failed to comfort her during her grief and threatened him with a divorce. He dared her to do it, and she did. Jerry recalled that unforeseen experience in May 2020:
“She said to me, ‘If you can’t maneuver this, I’m going to divorce you.’ And I said, ‘Oh yeah? I dare you.’ And the next day, I got divorce papers.”
Despite that, the lovebirds rekindled their romance one year later, in 1991, by remarrying, and they have been married ever since. The couple now resides in Florida with their three dogs.
In the book “What Makes a Marriage Last,” Judy shared that men and women are wired differently. She further supported her statement by saying:
“Women will accommodate men from the beginning, and after they get married, they say, ‘All right, you start accommodating me. You start changing.’”
Judy also discussed the do’s and don’ts for couples in her book, “What Would Judy Say? A Grown-up Guide to Living Together with Benefits.” She said she has nothing against people who prefer cohabiting before getting married, only if they have a plan for how they would go about it.
The television producer stated her number one rule for that setup: a set timeframe for how long it would go on. Secondly, she said couples should keep their properties separate.
Thirdly, Judy stated women should avoid falling pregnant before getting married. “I’m old fashioned in that respect,” she noted, adding it was all from experience:
“I would say it’s wise, live together, give it an old college try, if it doesn’t work, move on. And if it does, get married.”
Judy’s Five Adult Kids
Judge Judy had her first child, Jamie, in 1966 and later welcomed her second child, Adam, in 1968. She put her career on hold to raise them and has never regretted it.
However, boredom struck the Emmy Award winner while being a stay-at-home mom. That said, Judy returned to school to study for a Master’s in Family Law at New York University.
Five years later, the philanthropist also decided it was time to get back to work, but her then-husband disagreed; hence their marriage fell apart. They, too, as a couple, grew apart.
As for their kids, the duo’s daughter forged a path away from the Law profession and has kept a low profile ever since. However, the same cannot be said about Judy and Ronald’s only son, Adam, who followed in their footsteps. Adam made a name for himself by becoming the District Attorney (D.A.) in Putnam County, New York.
Unlike his older sister, Adam was thrust into the limelight in 2013 when he filed a $5 million defamation lawsuit against Putnam County Sheriff Donald Smith. The case went on for four years, and Adam ended up winning. Smith was ordered to pay him $150,000, accompanied by a public apology.
Meanwhile, Judy’s two stepkids, Gregory and Nicole, also pursued careers in Law. Gregory was the first to get his Doctor of Law (JD) from Brooklyn Law School in 1989.
Gregory began his legal career as an Assistant District Attorney at the New York County District’s Attorney Office and spent four years as a trial attorney. He became a partner in Sheindlin & Sullivan, LLP, then opted to open Sheindlin Law Firm in 2014.
Like his stepbrother, Adam, he too has had his fair share of high-profile legal dramas. In 2009, a man named James H. Brady failed to pay his rent, and Gregory took over the case to represent the Manhattan commercial landlord taking Brady to court.
Brady was found guilty but retaliated by filing lawsuits to overturn the verdict in the years that followed. He sued many defendants, including Gregory, and claimed the judgment was falsified to rake millions from him. In total, he had to cough up $1.7 million.
Gregory’s sister Nicole initially studied for a Bachelor’s Degree in Design and Applied Arts from the University at Buffalo. She later obtained a Doctor of Law (JD) from New York Law School in 1993.
Nicole started her law career as a Senior Attorney in the Criminal Defense Division of The Legal Aid Society. But she left in 2007 to become a partner in her private practice, Mentzer & Sheindlin. Nicole also founded a mentoring program and is an avid traveler, having been to 38 countries.
Unlike his siblings and parents, Jonathan is the only family member with a different career field. He obtained his Medical Degree (MD) from the New York Medical College and completed his residency in Ophthalmology at St. Luke’s/Roosevelt Hospital Center. He has since been working as an ophthalmologist.
After raising kids who became successful, Judy and her husband Jerry were blessed with grandchildren. The proud grandmother became emotional when speaking about the couple’s first grandchild, recalling the day she first saw him on the day he was born:
“[…] I looked at him, and I thought that he was the most spectacular baby I had ever seen. […] There’s something different about our first grandchild.”
Meanwhile, the doting grandfather Jerry, also reminisced on the memories they shared with their grandson and revealed 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 Officiated Her First Grandchild’s Wedding
Jerry’s wife was even more honored when asked to officiate their eldest grandchild Casey Barber’s wedding, as he married his college sweetheart, Olivia Weil. The newlyweds are both lawyers, having met in Law School.
Casey and Olivia tied the knot in September 2013 in a lavish wedding ceremony on Judy’s estate in Greenwich, Connecticut. There were 150 guests in attendance at the nuptials.
The television star’s grandson Barber and her granddaughter, Sarah Rose, are both lawyers out of her many grandchildren.
Besides following in her footsteps, they also look like her. Judy posted a throwback image of herself in January 2018 captioned, “#TBT Judge Sheindlin growing up as a young girl in Brooklyn!” and it showed her striking resemblance to her grandchildren.
Judy has 13 grandchildren, some are still just infants and several of them already have careers and families, and although she is best known for her toughness and her “no-nonsense” approach in the courtroom, she admitted to being a softie when it comes to them:
“I spoil them. I’m trying to think of how we don’t, but the answer is we do.”
However, that does not entirely mean she is not strict with them. Her grandchild Sarah revealed that at home, she gives them tough love:
“That’s still there. The no-nonsense grandmother is still there. But there is a much softer, supportive side.”
Sarah added that her grandmother is always the first person she contacts whenever she has an issue or needs a problem solver because Judy does an excellent job at solving problems.
Moreover, she revealed that her family is full of lawyers who discuss legal matters during dinner. Sarah said she always felt left out of the conversations her aunts and uncles used to have at the dinner table when she was young and wanted to be able to engage with them in the future.
That is why she, too, pursued a law career and ultimately learned how to “communicate and think like a lawyer.” With that, she could converse with her loved ones at home and expressed gratitude for achieving that.
In addition, Sarah felt fortunate to have her beloved and famous grandmother hand her her diploma during her commencement speech at New York Law School. In a 2022 interview, she spoke warmly about the impact Judy has had 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 piece of advice she’s ever given me.”
Sarah, who calls Judy “Nana,” penned a heartfelt tribute to her in November 2021. She shared one of her fondest childhood memories of when she and her siblings, cousins, aunts, and uncles would reunite at her lake house for the weekend.
“[…] The home videos of everyone laughing, all bundled up, and spending time together, shows 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.”
Sarah concluded her homage to her loving grandmother by saying she is fortunate to have her as her “biggest cheerleader and supporter – and very best friend.”
When Judy ended her long-running “Judge Judy” show, she returned to the screen with her protégé granddaughter for the show’s spin-off, “Judy Justice,” where Sarah serves as a law clerk.