Stephen Cloobeck, a Los Angeles timeshare mogul who spent more than $1 million backing a scandal-plagued Democratic candidate for California governor, has now maxed out his donations to the Republican in the race, a party switch that captures a widening rift between wealthy donors and the Democratic establishment.

State campaign records show Cloobeck cut a $39,200 check, the maximum allowable contribution, to Republican Steve Hilton's gubernatorial campaign on Tuesday, The California Post reported. The contribution came from a man who called himself a loyal Democrat for more than four decades before publicly torching that allegiance earlier this year.

Hilton, who faces Democrat Xavier Becerra in the general election, said the donation arrived unsolicited. "I didn't ask for his support, he just did it," Hilton told the outlet. A mutual friend in Los Angeles introduced the two men, and they have met several times since, though Hilton said they have not spoken recently.

Cloobeck's break with Democrats began with Eric Swalwell's downfall

Cloobeck's rightward drift traces directly to former congressman Eric Swalwell, the onetime Democratic frontrunner in the governor's race whose campaign collapsed under rape and sexual assault allegations. Cloobeck had been Swalwell's most generous patron, giving him a maximum $39,200 campaign contribution and a $31,000 trip to France in 2024. He let Swalwell stay frequently at his Beverly Hills mansion and spent more than $1 million in total propping up the gubernatorial bid.

When the allegations surfaced, Swalwell filmed a video denying the sexual misconduct claims from inside Cloobeck's mansion. The billionaire was not amused. He kicked Swalwell out and severed ties. Swalwell suspended his campaign and resigned from Congress amid the mounting accusations.

Cloobeck told The California Post earlier this spring exactly what he thought of his former party:

"F--- you, Democrat Party. I'm a libertarian now."

He added: "I am done, finito."

Cloobeck had previously said he planned to change his party registration entirely. Fox News reported that Cloobeck declared himself both a libertarian and a Republican in separate statements, telling the New York Post he could no longer "stand this Democratic Party at all." He had backed Swalwell since 2017, donating $23,400 over the years and providing gifts including a nearly $40,000 flight to Nice, France.

Cloobeck did not respond to a request for comment on the Hilton contribution.

Hilton frames the race as a business turnaround for California

Hilton cast the donation as evidence that even lifelong Democrats recognize the state's dysfunction. In a statement, he described his conversations with Cloobeck 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."

The Republican candidate is preparing for his first general election debate against Becerra, scheduled for September 30. Hilton suggested more debates should follow, noting that Becerra, when pressed, acknowledged "there will be debates, plural." Whether additional matchups materialize remains an open question.

Cloobeck's party flip is not an isolated event. Democrats have watched a growing number of their own break publicly with party leadership over the past year, with elected officials and donors alike voicing frustration over the direction of the national brand.

Cloobeck briefly ran for governor himself, and faces his own legal troubles

Before writing checks for Hilton, Cloobeck briefly entered the governor's race himself in 2025. He dropped out and endorsed Swalwell, a decision he clearly regrets. The founder of Diamond Resorts, Cloobeck built his fortune in the timeshare industry and has been a fixture in California political circles for decades.

His own legal situation is far from clean. Prosecutors 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 involving Adva Lavie, described as Cloobeck's former fiancée, whom prosecutors accused of using dating apps to target wealthy older men before burglarizing their homes. Cloobeck pleaded not guilty to all counts in August.

The pending charges complicate Cloobeck's role as a political figure, though they have not stopped him from making his preferences known with his checkbook. His not-guilty plea remains pending, and the case's outcome could color how both parties treat his support going forward.

The broader political backdrop makes the donation more than a curiosity. California voters will decide in November whether to pass a wealth tax, a measure that could hit donors like Cloobeck directly. A wave of congressional departures has already reshaped the political landscape heading into the fall, and the Democratic Party's grip on its donor class looks weaker than it has in years.

Some Democrats have tried to distance themselves from the party's progressive wing on economics and governance. But when a billionaire who funded your gubernatorial frontrunner to the tune of seven figures switches sides and maxes out for the Republican, the problem goes beyond messaging. It is a revolt inside the ranks that money makes loud.

Hilton now enters the fall campaign with a tangible symbol of Democratic dysfunction bankrolling his effort. Whether Cloobeck's money moves the needle in deep-blue California is one question. Whether his defection signals a broader realignment among wealthy donors is a bigger one, and one the Democratic Party cannot afford to ignore.

When the people who wrote the biggest checks start crossing the aisle, the party's problem is not the donor, it is what drove him out the door.