Millionaire Stephen Cloobeck, who is running for governor of California as a Democrat, knows that throwing money at a challenge doesn’t always work.
The time-share entrepreneur saw the 2020 end of his five-month relationship with girlfriend Stefanie Gurzanski get ugly, litigious and public. Cloobeck, 58 when he met the OnlyFans model and Instagram influencer, spent over $1 million on Gurzanski, hosting a $130,000 party for her 26th birthday, buying her a $200,000 Richard Mille watch, and prepaying her annual rent on a luxurious Beverly Hills apartment. He claimed he didn’t know she was shooting porn on his property and posting it on OnlyFans, and said he broke up with her when he found out.
But when it comes to his business acumen and wealth — which Inside Edition put at around $100 million in 2021 — Cloobeck is far more successful.
And he’s willing to throw some big money at the long-shot challenge of becoming California’s next governor.
The former CEO of Diamond Resorts has the most money in his coffers among all 2026 California gubernatorial contenders, raking in $13.6 million via 172 contributions, according to California Secretary of State records.
Granted, he contributed $13 million of the total, but he got some contributions from real estate executives, including $72,800 from William Meldman, chairman of Discover Land Company, a Scottsdale, Arizona-headquartered real estate developer and operator of private residential communities and resorts. Cloobeck reeled in another $20,500 from five Discovery Land Company employees.
Cloobeck, who turns 64 on Sunday, also received $51,400 from family-owned real estate investment firm Randall Realty Group, led by James Randall, the airplane rivet king-turned-philanthropist, and $36,400 from Jim Murren, former CEO of MGM Resorts International. Residential agent Josh Altman, co-founder of The Altman Brothers at Douglas Elliman, who shot to fame on “Million Dollar Listing Los Angeles,” shelled out $1,500.
Beyond real estate, actress and comedian Tiffany Haddish supported Cloobeck with a $2,500 donation, director Brett Ratner gave $1,000 and actor and comedian Tom Arnold contributed $500.
The first-time political candidate, who once considered a run for governor of Nevada, announced his bid for California’s top elected office about a year ago but only recently garnered attention atop the money list among candidates.
His slogan is “California, Get a Cloo.” (He is giving away merchandise.)
He is one of many candidates competing to succeed Gov. Gavin Newsom, who is term-limited and ineligible for reelection in 2026.
How he got here
Cloobeck, who started out as a busboy in a small California restaurant, built his first shopping center in the 1980s in Burbank, California, and others in Bakersfield, Hanford, Hemet, Buena Park and Mission Viejo. He built his first hotel, the Polo Towers, on the Las Vegas Strip.
He founded Las Vegas-based Diamond Resorts International in 1992. The company acquired the publicly traded Sunterra Corporation in 2007 for $700 million, helping Diamond Resorts to become the second-largest vacation ownership company.
By 2016, Diamond Resorts had a network of more than 420 vacation destinations in 35 countries. Cloobeck sold Diamond Resorts to private equity firm Apollo Global Management in a 2016 deal expected to total $2.2 billion.
Cloobeck was named Nevada Athletic Commission chairman for a two-year term in June 2021. He resigned in late 2022, saying he would not be able to work with Gov. Joe Lombardo, a Republican who took office in early 2023.
The matter seemed more personal than ideological.
“He is not honest nor grateful for the great benefits I’ve given to the State of Nevada,” Cloobeck said at the time.
As chairman of the Athletic Commission, Cloobeck pressed for the cause of death in the case of Nathan Valencia, 20, who collapsed in the ring after a University of Nevada-Las Vegas fraternity-sponsored boxing match. Cloobeck successfully pushed the commission to pass “Nathan’s Law” which requires trained referees and on-site medical personnel at amateur boxing events — but noted in his resignation that then Clark County Sheriff Lombardo did nothing to help his effort.
Other past appointments were serving as the inaugural chairman of the board of Brand USA Inc., a United States government-formed nonprofit corporation to promote travel to the U.S.; and a member on Nevada’s Standing Committee on Judicial Ethics and Election Practices, a board that attempts to settle ethical disputes that may arise over the course of campaigns for judicial office.
A native of the Encino district in the San Fernando Valley, Cloobeck received a degree in bio-psychology from Brandeis University in 1983. He lives in a Beverly Hills mansion. Twice divorced, Cloobeck has three grown children. After his father went bankrupt, Cloobeck supported him until he passed away, per Vanity Fair.
“The internet says I’m only worth $100 million, which is just fine with me,” he told Vanity Fair in 2021. “My house in Beverly Hills is worth $100 million, and I own a $45 million home for cash in Cabo, and I own my own jet. You can do the math yourself.”
Cloobeck appeared on several episodes of the reality-television show “Undercover Boss,” working low-level jobs at Diamond Resorts International to see a different side of the business.
In June, the candidate released his second book, “Facing Hard Truths: How Americans Can Get Real, Pull Together, and Turn Our Country Around.” The book covers topics including immigration, crime and the cost of living. His first book, “Checking In: Hospitality-Driven Thinking, Business, and You,” came out in October 2018.
Real estate heavyweights back Villaraigosa’s 2026 bid for governor
Laguna Beach home connected to timeshare mogul asks $40M