Stephen Cloobeck, a Los Angeles timeshare mogul who spent more than $1 million propping up Eric Swalwell's gubernatorial bid, has maxed out his donations to Republican Steve Hilton's campaign for California governor, capping a bitter break with the Democratic Party.
Cloobeck gave $39,200, the maximum allowed under state law, to Hilton's campaign, state campaign records show. The contribution landed the same week Hilton prepares for a September 30 general election debate against Democrat Xavier Becerra. For a man who said he spent more than four decades as a loyal Democrat, the check to a Republican governor's race marks a sharp and public reversal.
The money trail tells the story of a donor who went all-in on Swalwell, and got burned. Cloobeck previously gave Swalwell the same $39,200 maximum campaign contribution, funded a $31,000 trip to France for the then-congressman in 2024, and let Swalwell stay frequently at his Beverly Hills mansion. In all, Cloobeck spent more than $1 million supporting Swalwell's bid for governor.
That investment collapsed when multiple women accused Swalwell of rape, sexual assault, and other sexual misconduct. Swalwell denied the allegations. He filmed a video denying the claims from inside Cloobeck's own home, a detail that apparently did not sit well with his benefactor.
Cloobeck severed ties. He kicked Swalwell out of the Beverly Hills mansion and told The California Post earlier this spring that he was finished with the Democratic Party entirely.
His language left no room for interpretation. In a previous interview with the outlet, Cloobeck said:
"F--- you, Democrat Party. I'm a libertarian now."
He added: "I am done, finito." Cloobeck said he planned to change his party registration after more than four decades as a Democrat.
Hilton, the Republican nominee, said the donation came unsolicited. A mutual friend in Los Angeles introduced the two men, and they met several times, though Hilton said he has not spoken with Cloobeck recently.
"I didn't ask for his support, he just did it."
Hilton framed their conversations around a shared frustration with how California has been run.
"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 did not immediately respond to a request for comment on the donation.
The donor's break with Democrats is not the only turbulence in his life. 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. He briefly ran for California governor himself in 2025 before dropping out of the race.
Hilton now turns his attention to the first, and what he described as likely the only, general election debate against Becerra on September 30. Hilton pushed for more face-offs, noting that Becerra, when pressed, said "there will be debates, plural. There should be more."
California voters will also decide in November whether to pass a proposed wealth tax that would reshape the state's fiscal landscape. The combination of a competitive debate stage and a high-stakes ballot measure gives Hilton an opening to make the business-turnaround case Cloobeck's money now backs.
When a man who gave a party more than four decades and more than a million dollars walks out the door and writes a maximum check to the other side, that is not a tantrum. That is an exit interview, and California Democrats ought to read it carefully.
