A Los Angeles billionaire who spent more than $1 million backing a Democrat for California governor has now written the maximum check to the Republican in the race, a party switch four decades in the making.
Stephen Cloobeck, the timeshare mogul who once bankrolled former congressman Eric Swalwell's gubernatorial campaign, made a $39,200 contribution, the maximum allowed under state law, to Republican Steve Hilton's campaign for California governor, state campaign records show. The contribution landed Tuesday, capping a dramatic break from the Democratic Party that Cloobeck had telegraphed for months.
Cloobeck's defection is not a quiet hedge. He poured more than $1 million into Swalwell's bid, gave Swalwell the same $39,200 maximum donation, funded a $31,000 trip to France for him in 2024, and let the then-congressman stay regularly at his Beverly Hills mansion. When Swalwell's campaign collapsed under rape and sexual assault allegations, which Swalwell denied, Cloobeck kicked him out of the house and publicly cut ties.
Earlier this spring, Cloobeck told The California Post exactly where he stood. He said he had been a Democrat for more than four decades and planned to change his party registration.
His language left no room for interpretation. As The California Post reported:
"F, you, Democrat Party. I'm a libertarian now. I am done, finito."
Cloobeck did not respond to a request for comment on the Hilton contribution. But Hilton said the donation came unsolicited.
"I didn't ask for his support, he just did it."
Hilton said a mutual friend in Los Angeles introduced the two men, and that they have met several times, though they have not spoken recently. In those conversations, Hilton said, they found common ground on the state's direction.
"In our conversations, we've agreed that California is a complete mess in terms of its management and it needs a common-sense, business-like turnaround."
Cloobeck's journey from Democratic megadonor to Republican contributor tracks directly through the wreckage of Swalwell's political career. Swalwell had been Cloobeck's chosen candidate, lavishly funded, personally housed, and publicly supported. When sexual misconduct allegations surfaced, Swalwell filmed a video denying the claims from inside Cloobeck's Beverly Hills home. Cloobeck responded by throwing him out of the mansion and walking away from the campaign entirely.
Cloobeck briefly ran for governor himself in 2025 before dropping out. His decision to back Hilton now represents the final step in a break that began with Swalwell's implosion and widened into a wholesale rejection of the party he had supported for decades.
The billionaire donor is not without complications of his own. Prosecutors have charged Cloobeck with three felony counts of attempting to dissuade or prevent a witness or victim from testifying and one misdemeanor count of making annoying phone calls. The charges stem from the criminal case of his former fiancée, Adva Lavie, whom prosecutors accused of using dating apps to target wealthy older men before burglarizing their homes. Cloobeck pleaded not guilty to all charges in August.
Those charges hang over his political activity but have not stopped him from putting his money squarely behind the Republican ticket in California's governor's race.
Hilton is now preparing for his first, and what he described as likely his only, general election debate against Democrat Xavier Becerra, scheduled for September 30. Hilton pushed for more.
"[Becerra] said when he was pressed on this that there will be debates, plural. There should be more."
California voters will also face a wealth tax ballot measure in November, a proposal that could accelerate the kind of donor flight Cloobeck's switch represents. For a party already watching billionaires walk out the door, that timing is not a coincidence, it is a consequence.
When a man who spent four decades and millions of dollars propping up Democrats decides to max out for a Republican, the message is not complicated. He looked at what his money bought, and he wanted a refund.
