Billionaire Stephen Cloobeck Arrested on Felony Witness Tampering Charges Tied to His Fiancée's Case
Stephen Cloobeck — billionaire founder of Diamond Resorts International, former Democratic megadonor, and briefly a California gubernatorial candidate — was arrested Tuesday morning in West Hollywood on felony charges of witness tampering. He was released the same day after posting $300,000 bail.
The arrest adds a dramatic new chapter to one of the more turbulent trajectories in recent California political and social circles — a story that in the span of a few months has involved a major political figure's sexual misconduct scandal, a high-profile friendship collapse, a party switch, and now a felony booking.
The Charges
The Los Angeles County District Attorney's Office charged Cloobeck with three felony counts of attempting to prevent or dissuade a witness or victim from attending a legal proceeding by force or threat. He also faces a misdemeanor charge of making annoying phone calls. The alleged conduct occurred between last December and this February. Charges were formally filed on April 28.
The connection to the charges quickly became clear. Cloobeck's fiancée, Adva Lavie — described in reports as a former Penthouse Pet — is facing multiple felony theft charges. Prosecutors allege she targeted wealthy men through dating apps and social circles, allegedly stealing luxury goods, cash, and personal information. She has pleaded not guilty.
According to prosecutors, Cloobeck attempted to dissuade or prevent three of Lavie's alleged victims from testifying against her. The misdemeanor charge involves alleged annoying phone calls to a fourth man connected to her case.
The investigation is being conducted jointly by the Malibu/Lost Hills Sheriff's Station and the Los Angeles Police Department.
Cloobeck's attorney Elias Dabaie pushed back on the charges directly. "These charges are false, and we look forward to our day in court," a spokesperson said.
The Political Backstory
Cloobeck's arrest comes after a year of highly public political drama. He entered the race for California governor in 2025 as a Democrat — one of several candidates jockeying to succeed Gavin Newsom — before dropping out in November 2025. He then threw his support behind former Rep. Eric Swalwell's gubernatorial campaign.
Swalwell and Cloobeck had been longtime friends. Swalwell had stayed at Cloobeck's Los Angeles-area mansion while campaigning. Then sexual misconduct allegations against Swalwell began surfacing, and Cloobeck's reaction was swift and very public.
He cut ties with Swalwell, told him to leave his home, and publicly confronted him about the allegations — saying Swalwell had apologized before departing. He then withdrew his endorsement and made clear he was done with the relationship. "I am no longer supporting Eric," he told a reporter, adding that he was now identifying as a libertarian. Swalwell has since resigned from Congress.
The fallout from that very public break was still fresh when Tuesday's arrest was announced.
Who Cloobeck Is
Cloobeck, 64, built Diamond Resorts International into one of the largest timeshare and vacation ownership companies in the world before selling it to Hilton Grand Vacations in 2021 for $1.4 billion. He had been a prominent Democratic fundraiser for years, donating to and appearing alongside major party figures before his political evolution began.
His decision to run for governor was framed as an outsider business candidacy. His November 2025 withdrawal came before the race had fully taken shape. His subsequent endorsement of Swalwell and then the very public collapse of that alliance played out across California political media for months.
Now Cloobeck faces a legal battle that his team insists is baseless. A criminal case in which a billionaire is accused of attempting to shield his fiancée from prosecution by leaning on her alleged victims is the kind of story that tends to generate considerable attention — and this one already has.
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