Stephen Cloobeck Net Worth

What is Stephen Cloobeck's net worth?

Stephen J. Cloobeck is an American businessman who has a net worth of $500 million. Stephen Cloobeck earned his fortune as the founder of the timeshare company Diamond Resorts International. He became more widely known after being featured on the reality series "Undercover Boss."

As we detail throughout this article, Stephen earned a huge fortune thanks to Diamond Resorts International. The exact size of the fortune is not known. What is known is that in 2016, Stephen sold Diamond Resorts for $2.2 billion in cash. At the time of the sale, he owned around 22% of the company's equity, which translated into a $500 million pre-tax windfall.

Stephen has claimed in various interviews to be a billionaire. That is certainly possible. He owns a home in Beverly Hills that he claims to be worth $100 million and a home in Cabo that he claims to be worth $45 million. He has also been divorced twice. He and his first wife, Heather, were married for 13 years. He was then married to a model named Chantal Leduc from 1997 to 2018. Chantal received their former $40 million mansion in Laguna Beach in the divorce, and presumably other assets, especially considering the divorce occurred AFTER the sale of his company and AFTER 20+ years of marriage. In 2024, Stephen announced his candidacy for the 2026 California Governor's race. Hopefully, he'll release a detailed financial statement to confirm or deny his billionaire status.

Early Life and Career Beginnings

Stephen Cloobeck was born on October 26, 1961. He graduated from Brandeis University in 1983 with a degree in Psychobiology. He initially intended to become a surgeon or a lawyer and was accepted into both medical and law school. It's unclear how or when his path changed, but he soon found himself building shopping centers in Southern California. His first shopping center project was in Burbank. He went on to build shopping centers in a half dozen other SoCal cities before moving on to Las Vegas. In 1991, he began construction on a hotel in Las Vegas. In 1992, the 21-story Polo Towers hotel opened on the Strip.

Diamond Resorts International

In 1992, Stephen founded Diamond Resorts International. He grew the company to a point where it operated more than 370 resorts around the world that specialize in timeshares. The company's resorts are located in 35 different countries and more than 400,000 people use Diamond's hotels each year for their vacations. In April of 2007, he acquired the publicly the Sunterra Corporation.

In June 2016, Stephen sold his timeshare assets to Apollo Global Management for $2.2 billion in cash, a 26% premium to its previous closing price. Cloobeck, the majority owner, walked away with $500 million in cash. Today, Diamond Resorts is owned by Hilton.

(Photo by Leonard Ortiz/MediaNews Group/Orange County Register via Getty Images)

Other Work and Politics

In addition to serving as the CEO of Diamond Resorts, he is the Chairman of the Board for the US Corporation for Travel Promotion and the Nevada Cancer Institute. He founded the Brent Shapiro Foundation for Drug Awareness and also gave the Brandeis University International Business School a significant endowment in 2012. He is very politically active and considered running for governor of Nevada in 2007. In November 2024, Stephen announced his intention to run for Governor of California in 2026.

Undercover Boss

Stephen became more well-known after appearing on the reality series "Undercover Boss." He first appeared on the series in January 2012 on season 3, episodes 1 and 2. He has gone on to make numerous appearances on the series.

Personal Life

Stephen and his first wife, Heather, were married for 13 years. In 1997, he married Chantal Leduc, a Canadian model who won Star Search in 1993. They divorced in 2018. They have three children together.

OnlyFans Girlfriend + Lawsuit

In 2020, Stephen began dating an OnlyFans model named Stefanie Gurzanski. They met through a matchmaker. In December 2020, he reportedly spent $130,000 throwing Stefanie a 36th birthday party at his Cabo San Lucas house with give of her girlfriends. Stephen, who would have been 59 years old on the day of his girlfriend's 26th birthday, flew the group to Cabo on his Bombardier Global Express private jet. As a birthday present he reportedly gifted her $200,000. He reportedly spent $1.3 million on Stefanie during the FIVE months they dated. It was later alleged by Cloobeck that Stefanie demanded $2 million in cash and a $7 million house in exchange for giving up her OnlyFans account. In January 2021, Stephen sued Stefanie, claiming various offenses, notably fraud and trespassing. A few weeks later, he filed an amended complaint that demanded the return of his money and property. At one point, Stefanie requested a temporary restraining order against Stephen, claiming she was "in fear for my life and well-being.". The restraining order was granted. For his part, Stephen was upset upon learning that Stefanie took nude photos without his permission in various rooms of his various mansions, his private jet, his private suite at a hotel in Las Vegas and more. She would then post those photos on OnlyFans. In September 2020 she allegedly took a nude photo wearing a yarmulke from his son's bar mitzvah and posted it on Rosh Hashanah, a significant Jewish holiday.

Real Estate

Upon their divorce, Chantal took ownership of a $40 million mansion in Laguna Beach. They bought the home in 2007 for $10.5 million. Stephen owns homes in Los Angeles, Las Vegas, and Cabo San Lucas. His Cabo home is reportedly worth more than $45 million.

After paying $19 million for his Beverly Hills mansion, Cloobeck spent years waiting for city approval to construct his 16,000-square-foot dream mansion. He finally won approval in February 2017. He named the finished product "Papillon," which means "butterfly" in French. Cloobeck has claimed this house is worth $100 million.

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