Stephen J. Cloobeck: Fortune, Politics, and Witness Tampering Arrest

Stephen J. Cloobeck is a California real estate developer, the founder and former CEO of Diamond Resorts International, a two-time Undercover Boss participant, and a former top Democratic donor who ran briefly for California governor in the 2026 cycle. In May 2026, Los Angeles County prosecutors charged him with three felony counts of attempting to dissuade a witness and one misdemeanor count of making annoying telephone calls, accusing him of trying to block testimony against his fiancée in a separate criminal case.¹

The May 2026 Witness Tampering Arrest

Cloobeck surrendered to the Los Angeles County Sheriff’s Department at its West Hollywood station on May 12, 2026. The District Attorney’s Office had filed the criminal complaint the previous month.²

Prosecutors allege Cloobeck tried to prevent three male victims from testifying in the criminal case against his fiancée, Adva Lavie, and that his conduct was “committed by force and an express and implied threat of force and violence upon a victim.” The misdemeanor count concerns allegations that he contacted and threatened Lavie’s attorney, Lou Shapiro, along with Shapiro’s property and family.¹

He posted $300,000 bail and was released the same day. His attorney, Elias Dabaie, said: “These charges are false and we look forward to our day in court.” Arraignment is scheduled for August 7, 2026.¹

The Case Against Adva Lavie

Lavie, 28, is a model and social media influencer who also uses the name “Mia Ventura.” She faces six felony charges: two counts of unauthorized use of personal identifying information, two counts of grand theft, and two counts of first-degree residential burglary. Prosecutors say she used dating apps between 2023 and 2025 to target wealthy men in Westlake Village, West Hollywood, Los Angeles, and Beverly Hills, posing as a girlfriend or travel companion to get inside their homes and take cash, gold, and designer items.³ She pleaded not guilty in April 2026 and was released on her own recognizance with an ankle monitor.² A conviction on all counts could carry up to 11 years and eight months in state prison.⁴

How He Built His Fortune

Cloobeck grew up in Encino, California, and earned a bio-psychology degree from Brandeis University in 1983. He briefly worked as a heart-research volunteer at Cedars-Sinai before shifting into real estate, developing shopping centers across California in the 1980s.⁵

In 2007, he led an investor group that acquired Sunterra Corporation, a timeshare company with nearly 100 resorts, and folded it together with his existing properties, including Las Vegas’s Jockey Club and The Carriage House, to form Diamond Resorts International. The company ran on a points-based ownership model aimed at giving members more flexibility than traditional deeded timeshares.⁶

Under Cloobeck, annual revenue grew from $371 million in 2010 to $954 million in 2015, and the business swung from a $19 million net loss to a $150 million profit over that period. Diamond Resorts went public on the New York Stock Exchange in 2013. In June 2016, Apollo Global Management announced a $2.2 billion all-cash deal to acquire the company. Cloobeck, who held close to a quarter of the stock, stood to collect roughly $346 million from the sale.⁶

Diamond Resorts drew consumer-protection scrutiny during his tenure. In January 2017, the company settled with the Arizona Attorney General over allegations its sales practices violated the state’s Consumer Fraud Act. Arizona had collected hundreds of complaints involving maintenance fee hikes, resale programs, and travel discounts. Diamond paid $800,000, of which $650,000 went to consumer compensation and $150,000 to state attorney fees, and agreed to change its sales presentations.⁷

Undercover Boss

Cloobeck is the first executive to have appeared on CBS’s Undercover Boss twice. The first episode aired January 15, 2012, as the Season Three premiere. Going undercover as “Jack Fischer,” he shadowed four Diamond Resorts employees and, after revealing himself, paid off one worker’s mortgage, bought another a new truck, cleared a third’s student loans, and helped a fourth cover her mother’s hospital bills.⁸ His second episode, “Diamond Resorts: Take 2,” aired November 30, 2012, and included more than $1 million in employee rewards.⁹

Politics: Big Democratic Donor, Then Not

Federal records show Cloobeck has given to Adam Schiff, Ruben Gallego, Barbara Lee, Kamala Harris, Mark Kelly, state Democratic committees in Nevada, Minnesota, California, and New York, and PACs including the Jane Fonda Climate PAC, Follow the North Star Fund, and Remedy PAC.¹⁰ By 2017 he was identified as Nevada’s largest national Democratic donor.¹¹

He has also quarreled with his own party. In a November 2017 MSNBC appearance, he called the party’s messaging on wealthy Americans “so effin’ wrong” and threatened to pull donations, saying, “If you use the term billionaires again, I’m done.” He said he had told Chuck Schumer, Ron Wyden, and Nancy Pelosi the same thing privately.¹²¹¹¹³

The 2026 California Governor’s Race

Cloobeck announced his candidacy for California governor on November 5, 2024, at a Beverly Hills watch party, running as a Democrat to replace Gavin Newsom. He put $3 million of his own money into the race in 2024. His platform, built around the slogan “California is not affordable, livable nor workable,” pushed easing the California Environmental Quality Act, overhauling insurance rules, revisiting AB 5, and demanding more accountability on homelessness spending.¹⁴ By September 2025 he was running television ads, some aimed at President Donald Trump.¹⁵

On November 24, 2025, Cloobeck dropped out and endorsed Representative Eric Swalwell, calling him “the most qualified person in the state.” He said he had only entered the race because he thought other candidates were not “capable of doing the job.”¹⁶ Cloobeck later said he gave the legal maximum of $39,200 directly to Swalwell’s campaign and $1 million through a supporting super PAC, and that he had spent roughly $7 million on policy research during his own run that Swalwell was free to use.¹⁷ His name did not appear on the June 2, 2026, primary ballot.¹⁸

During the campaign, Cloobeck tried to place bets on the race through the prediction market Kalshi, including $1,000 on Swalwell to win and $2,000 on San Jose Mayor Matt Mahan to lose. Kalshi blocked the trades, citing its rule against election bets by people with material, non-public information, though it did not give him a specific explanation.¹⁹

Break With Swalwell and the Democratic Party

The alliance ended in April 2026, when multiple women accused Swalwell of sexual assault. Swalwell denied the allegations but withdrew from the governor’s race and resigned from Congress. Cloobeck cut him off, evicted him from a Malibu property, and demanded his $1 million back, reportedly after Swalwell filmed a video denying the allegations from inside Cloobeck’s home.¹⁷²⁰ He also announced he was leaving the Democratic Party, telling the New York Post, “I’m a libertarian now. I am done. Finito.”

Earlier Civil Litigation

In January 2021, Cloobeck sued his former girlfriend, OnlyFans model Stefanie Gurzanski, in Los Angeles Superior Court for fraud and trespassing. He called her a “con artist” and alleged she had used his home, private jet, and credit cards to produce adult content without his knowledge, seeking to recover more than $1.3 million in gifts and luxury travel.²¹ Gurzanski denied the claims, obtained a temporary restraining order against him, and countersued for harassment, alleging he posted intimate images of her online without consent and published her address. A judge denied Cloobeck’s bid to lift the restraining order in April 2021. The available record does not show a final resolution of the case.²²

Philanthropy

In 2012, Cloobeck founded the Diamond Resorts International Foundation, originally called the Team Member Crisis Fund, to help employees facing emergencies. He has served as chairman of the Nevada Cancer Institute and donated $250,000 in 2022 to the Los Angeles Dream Center’s homeless families program.²³ His giving has gone to medical research groups including the Prostate Cancer Foundation, FasterCures, and Keep Memory Alive; to Brandeis University, UCLA, and the UNLV Foundation; and to the Anti-Defamation League, Homeboy Industries, and the United Farm Workers. He was executive producer of the CNN Films documentary Carville: Winning is Everything, Stupid.²⁴

1
Los Angeles Times. Cloobeck Arrest LA County
2
NBC Los Angeles. LA-Area Billionaire Stephen Cloobeck Arrested on Four Felony Counts
3
Los Angeles County District Attorney. Influencer Accused of Using Dating Apps to Target Victims Held to Answer on Six Felony Charges
4
ABC7 Los Angeles. Adva Lavie Held to Answer on 6 Felony Charges
5
Capitol Weekly. Better Know a CA Gubernatorial Candidate: Stephen Cloobeck
6
Forbes. Timeshare Resort Company Founder Is Big Winner in Apollo’s Latest Deal
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Timeshare Consumer Association. Diamond Resorts Are Ordered to Pay £800,000 in Way of Compensation
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Business Insider. CBS Show Undercover Boss: Stephen Cloobeck, Diamond Resorts International
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Paramount Press Express. Undercover Boss: Diamond Resorts: Take 2
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OpenSecrets. Stephen Cloobeck Donor Profile
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The Nevada Independent. Cloobeck, Huge Democratic Donor, Potential Gov. Candidate, Endorses Heller
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Washington Free Beacon. Major Dem Donor: Democratic Party’s Message ‘Effin’ Wrong’
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KNPR. Who Is Stephen Cloobeck
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Sacramento Bee. Stephen Cloobeck for California Governor
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ABC7 News. California 2026 Governor Candidates Hit Airwaves With New TV Ads
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CBS News Sacramento. Cloobeck Drops Out of CA Governor’s Race, Endorses Swalwell
17
Forbes. Near-Billionaire Backer of Eric Swalwell Goes to War With Him, Wants $1 Million Back
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California Secretary of State. 2026 Governor Election Returns
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Politico. Swalwell Ally Blocked From Prediction Market in California Governor’s Race
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Fox News. Billionaire Kicks Eric Swalwell From Mansion, Wants $1M Back
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Las Vegas Review-Journal. Timeshare Mogul’s Suit vs. Ex-Girlfriend Cites Lavish Gifts, Racy Pics
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Vanity Fair. Inside the Messy, Litigious Breakup of an OnlyFans Model and Her Uber-Wealthy Boyfriend
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StephenJCloobeck.com. Stephen J. Cloobeck Donates $250,000 to Los Angeles Dream Center
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StephenJCloobeck.com. Philanthropy