Stephen Cloobeck, a prominent Los Angeles timeshare mogul and former major donor to the Democratic Party, has made a maximum contribution of $39,200 to Republican Steve Hilton's campaign for California governor. The donation, made on Tuesday, signifies a significant shift in Cloobeck's political affiliations.
Hilton stated that he and Cloobeck share the view that California has been mismanaged and requires a "common-sense, business-like turnaround." Hilton mentioned that a mutual acquaintance introduced them, and while they have met several times, they have not spoken recently. "I didn’t ask for his support, he just did it," Hilton said.
Cloobeck's decision to support Hilton follows a public break with Democrats and, specifically, with former congressman Eric Swalwell. Cloobeck had previously invested over $1 million in Swalwell's gubernatorial bid. However, Cloobeck severed ties with Swalwell after multiple women came forward with allegations of rape, sexual assault, and other sexual misconduct against the former congressman. Swalwell has denied these allegations.
Cloobeck, who had been a Democrat for more than four decades, had previously allowed Swalwell to frequently stay at his Beverly Hills mansion, which even served as a location for Swalwell to film a video denying the allegations. Following the accusations, Cloobeck reportedly removed Swalwell from his mansion and declared his support for libertarianism, stating, "I am done — finito."
Cloobeck had also briefly run for governor in 2025 before withdrawing. In addition to his campaign contribution to Swalwell, he also provided him with a $31,000 trip to France in 2024.
In recent months, Cloobeck has faced his own legal challenges related to his former fiancée, Adva Lavie. Prosecutors have accused Lavie of targeting wealthy men through dating apps and subsequently burglarizing their homes. Cloobeck was charged 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, stemming from Lavie's case. Cloobeck pleaded not guilty to all charges in August.
Hilton is scheduled to participate in a debate against Democratic frontrunner Xavier Becerra on September 30. Hilton expressed a desire for more debates, stating, "There should be more."