Latest Update: Stephen Cloobeck's Total Wealth in Net Worth 2026: Career Earnings & Assets

As one of the most talked-about figures, Stephen Cloobeck has built a significant fortune. In this article, we dive deep into the assets and career highlights.

What is Stephen Cloobeck's net worth?

Diamond Resorts International

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.

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.

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.

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.

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."

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.

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.

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

In summary, the total wealth of Stephen Cloobeck reflects strategic moves.

Disclaimer: All net worth figures are estimates based on public data.