Judge Judy's wildest money moments over the years

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Judge Judith Sheindlin turns 80 on Oct. 21, 2022. To mark the occasion, Wonderwall.com is taking a look back at Judge Judy’s biggest money moments over the years — from massive deals to insane splurges and everything in between. Let’s start with this stat that’s sure to make your jaw drop… As of October 2022, Judge Judy is worth an estimated $440M! According to some estimates, she’s been worth as much as $470M in recent years.

Now keep reading for more of Judge Judy’s biggest money moments…

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In early 2017, reports indicated that Judge Judith Sheindlin was shopping the rights to “Judge Judy” reruns for a cool $200M. She ultimately sold the catalogue to CBS for just under $100M.

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In July 2018, Judge Judith Sheindlin ranked fourth (behind Floyd Mayweather, George Clooney and Kylie Jenner) on Forbes’s list of the world’s 100 highest-paid entertainers. She reportedly raked in $147M before taxes the previous year (nearly $100M for selling her catalogue of “Judge Judy” reruns to CBS, plus her annual salary of $47M per season of the hit TV show). She also came in No. 1 on Forbes’s list of the highest-paid television hosts that year.

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In its final years, Judge Judith Sheindlin’s hit TV show “Judge Judy” reportedly raked in an estimated $160M to $170M in licensing fees and advertising per year for CBS. The series ran for 25 seasons between 1996 and 2021.

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In the summer of 2018, Judge Judith Sheindlin snapped up the most expensive home sold in Rhode Island that year. According to the Providence Journal, Judge Judy dropped $9 million on the Bird House: a 9,700-square-foot, six-bedroom, eight-bathroom property on 3.67 acres in Newport, Rhode Island, that once belonged to the heir to the Campbell Soup fortune. The mansion, which was built in 2012, features geothermal heating and cooling, radiant heated floors, a three-floor elevator and more luxury amenities.

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Judge Judith Sheindlin — who lives primarily on the East Coast — reportedly owns a Cessna 750 Citation X private jet worth $24M. It’s an essential part of the equation considering Judge Judy works primarily in the Los Angeles area.

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According to Dirt, Judge Judith Sheindlin dropped $13.2M on a 12.54-acre property in Greenwich, Connecticut, in 2007. Judge Judy reportedly demolished the existing 11,623-square-foot, nine-bedroom mansion and built a 20,000-square-foot home in its place.

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In early 2021, Judge Judith Sheindlin dropped a $22M lawsuit against her former talent agent — the man who negotiated her initial deal with CBS for “Judge Judy” — when she realized the lawsuit would negatively affect CBS. “I have been in business with CBS for 20 years. I’m not suing them when they are not the wrongdoer,” she told Deadline of her costly decision. (She accused the former agent of unjust enrichment and of employing unlawful and unfair business practices.)

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In 2015, Judge Judith Sheindlin listed her four-bedroom penthouse apartment in Naples, Florida, for $11M. (According to Dirt, Judge Judy purchased the 8,550-square-foot condo for $6.9M in 2005.) The property features four full bathrooms, two half bathrooms, two high-speed private elevators and ocean views. The unit comes with parking for three cars in an air-conditioned garage, plus a private cabana/studio near the complex’s resort-style swimming pool. She had a good reason for unloading the luxury property…

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In 2015, Judge Judith Sheindlin dropped $8.6M on a nearly 11,000-square-foot lakefront mansion in a gated community in Naples, Florida. According to Dirt, Judge Judy’s six-bedroom property features nine full bathrooms, two half bathrooms, two air-conditioned three-car garages, an outdoor kitchen and a lagoon-style swimming pool with three waterfalls and a spa.

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In early 2022, Judge Judith Sheindlin donated $5M to Her Honor Mentoring to fund a scholarship program that will provide full tuition for 10 women at her alma mater, New York Law School. Judge Judy co-founded Her Honor Mentoring with her daughter, Nicole Sheindlin, in 2006.

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In 2013, Judge Judith Sheindlin sold her two-bedroom condo on the 11th floor of the Sherry Netherland building on New York City’s Fifth Avenue for $8.5M. According to Dirt, the unit featured two and a half bathrooms. Around the same time, Judge Judy snapped up another NYC pad…

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In 2013, Judge Judith Sheindlin dropped $8.5M on a four-bedroom duplex in New York City’s Sutton Place neighborhood. According to Dirt, Judge Judy’s NYC pad features four and a half bathrooms and a wrap-around terrace.

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Judge Judith Sheindlin once owned a yacht named the Triumphant Lady that she reportedly sold for nearly $7M at some point. Judge Judy’s 152-foot, five-cabin vessel featured a glass-bottom spa pool and a gym.

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In 2013, Judge Judith Sheindlin reportedly dropped $10.7M on a five-bedroom condo at the Montage Beverly Hills hotel and condo complex in the heart of Beverly Hills. The 4,680-square-foot unit features three and a half bathrooms, a walk-in wine cellar and seven balconies. Judge Judy’s Beverly Hills base also comes with four dedicated parking spots in an underground garage, plus all the amenities offered by a five-star hotel — from room service to laundry and housekeeping services.

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In 2020, TheRichest reported that Judge Judith Sheindlin owns “a whole fleet” of Bentleys including a 2007 Bentley Azure, a 2006 Bentley Arnage R and a 2016 Bentley Mulsanne. Judge Judy dropped more than half a million dollars on those three cars alone!

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In 2020, TheRichest reported that Judge Judith Sheindlin’s signature diamond stud earrings — which were practically a supporting character on “Judge Judy” — are worth an estimated $120K.

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In 2018, Judge Judith Sheindlin reportedly dropped $40K on a three-wheel Harley-Davidson motorcycle for her husband’s 85th birthday. (Judge Judy married fellow judge Jerry Sheindlin in 1977 and again in 1991 after a brief split.)

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Judge Judith Sheindlin once forked over more than $50K to “Judge Judy” executive producer Randy Douthit for some Christofle Mary Bone China and cutlery. The transaction came to light in early 2013 when Randy’s estranged wife, Patrice Jones, sued the TV judge for more than $500K, claiming that the posh tableware was community property and that Randy had no right to sell it to Judy without her consent. (Judy ultimately returned the items to Patrice, who alleged that Judy conspired with Randy to make the deal as Patrice and Randy geared up to divide their assets as part of their divorce.)

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In early 2014, Judge Judith Sheindlin filed a $75K lawsuit against a personal injury attorney who used her image in advertising without her consent. The duo settled out of court in Judge Judy’s favor. Per the terms of their settlement, the lawyer made a charitable donation to Judy’s mentoring program, Her Honor Mentoring.

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In early 2018, two former “Judge Judy” producers sued Judge Judith Sheindlin and CBS for $4.75M for allegedly cutting them out of profits for the show they helped create back in 1995 after they essentially discovered the TV judge. Ultimately, the court sided with Judy and CBS in early 2022.























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