Stephen Cloobeck, the billionaire who spent more than $1 million propping up Eric Swalwell's gubernatorial campaign, has maxed out his donation to Republican Steve Hilton, capping a dramatic party defection.

Cloobeck, a Los Angeles timeshare mogul and founder of Diamond Resorts, gave $39,200, the maximum allowed under California law, to Hilton's campaign for governor, state campaign records show. The contribution landed Tuesday, less than a month before Hilton's first scheduled general election debate against Democrat Xavier Becerra on September 30.

The donation marks the most concrete step yet in Cloobeck's break with the Democratic Party, a relationship he says lasted more than four decades. It also hands Hilton a symbolic win: one of the California left's most generous financiers is now writing checks for the other side.

From Swalwell's Beverly Hills host to his fiercest critic

Cloobeck's journey from Democratic megadonor to Republican contributor runs directly through the wreckage of Swalwell's political career. The billionaire had been one of Swalwell's most lavish backers, previously giving the former congressman the same $39,200 maximum donation, funding a $31,000 trip to France in 2024, and letting Swalwell stay frequently at his Beverly Hills mansion.

All told, Cloobeck poured more than $1 million into Swalwell's gubernatorial bid.

Then came the sexual misconduct allegations. Multiple women accused Swalwell of rape and sexual assault, and his campaign collapsed. Swalwell denied the allegations, at one point filming a denial video from inside Cloobeck's own home. Cloobeck responded by severing ties and removing Swalwell from the mansion.

Fox News reported that Cloobeck's donations to Swalwell's campaigns stretched back to 2017, totaling at least $23,400 in direct political contributions on top of gifts that included a flight to Nice, France valued at $39,900. The outlet described Cloobeck's break as part of a broader disillusionment with the Democratic Party that went well beyond Swalwell personally.

Cloobeck did not hold back when he announced the split earlier this spring. He told The California Post he planned to change his party registration entirely.

"I'm going to change my G**d*** party affiliation, because I cannot stand this Democratic Party at all. I am done. Finito."

He went further in the same interview, declaring himself a libertarian and directing an expletive at the party he had funded for decades: "F*** you, Democrat Party. I'm a libertarian now." He later told the outlet he now considers himself a Republican.

Hilton says Cloobeck donated without being asked

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 they have not spoken recently.

"I didn't ask for his support, he just did it."

Hilton framed the contribution as a sign that frustration with California's governance crosses party lines. He described the state's condition in blunt terms.

"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 respond to a request for comment from The California Post.

The donation is not Cloobeck's first flirtation with the governor's race from a different angle. He briefly ran for governor himself in 2025 before dropping out. Now he is backing the Republican he believes can deliver the management overhaul he wanted to lead himself.

Cloobeck's defection fits a pattern that extends beyond California. A prominent Democratic donor recently raised money for a Republican in New York's governor's race, suggesting that big-dollar frustration with the party is not confined to a single state or a single scandal.

Cloobeck faces his own legal troubles

The billionaire's political transformation comes as he navigates serious criminal charges of his own. Prosecutors have charged Cloobeck with three felony counts of attempting to dissuade or prevent a witness or victim from testifying, plus one misdemeanor count of making annoying phone calls. The charges stem from the criminal case involving Adva Lavie, described as Cloobeck's former fiancée.

Prosecutors have accused Lavie of using dating apps to target wealthy older men before burglarizing their homes.

Cloobeck pleaded not guilty to all charges in August. The case adds a volatile personal dimension to a political story that already involves allegations of sexual misconduct, a collapsed campaign, and a donor revolt.

Neither Hilton nor his campaign addressed Cloobeck's legal situation in the remarks captured by The California Post. Whether the charges complicate the donation's political value remains an open question heading into the fall campaign.

California's November ballot looms over the race

Hilton is preparing for what he described as likely his only general election debate against Becerra, scheduled for September 30. He pushed for more, citing Becerra's own words.

"[Becerra] said when he was pressed on this that there will be debates, plural. There should be more."

The governor's race unfolds against a broader backdrop of Democratic Party upheaval. California voters will decide in November whether to pass a wealth tax ballot measure, a proposal that has already drawn fierce opposition from the state's billionaire class. Google co-founder Sergey Brin has reportedly spent $100 million fighting the measure, according to prior California Post reporting.

The internal Democratic infighting visible at the national level has a California flavor: the party is simultaneously trying to hold its donor base, manage a governor's race shadowed by the Swalwell scandal, and defend a tax proposal that is driving wealthy residents toward the exits.

Swalwell, meanwhile, could face additional legal exposure. Prior reporting from The California Post indicated he may face abuse-of-power claims, though the current status of any such proceedings remains unclear. He has continued to deny the sexual misconduct allegations.

The Democratic Party is also contending with what The California Post described as "a revolt among billionaires." Cloobeck is the most dramatic example, a man who spent decades and millions building relationships inside the party, only to fund its opponents after a single season of scandal and disillusionment.

The broader question of where the Democratic Party is headed hangs over races well beyond California. But the state's governor's contest, with its mix of personal betrayal, criminal charges, and donor flight, offers the sharpest picture of a coalition under strain.

Hilton enters the final weeks of the campaign with a donor who once embodied Democratic generosity now standing on his side of the ledger. Whether more follow depends on how many other lifelong Democrats look at California's trajectory and reach the same conclusion Cloobeck did.

When a party's biggest donors start funding the opposition, the problem is not one bad candidate. It is the party itself.