Cloobeck Invests Heavily in Governor Race TV Ads
California Gubernatorial Race Heats Up as Cloobeck Launches New Ad Blitz
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Stephen Cloobeck, a Beverly Hills philanthropist and businessman, is intensifying his campaign for California governor with a new round of television and digital advertising, even as the field of candidates remains largely unknown to voters. The ads, running through Monday, will air in key media markets including Washington D.C. and West Palm Beach, Florida – the location of former President Trump’s Mar-a-Lago.
Cloobeck’s Early and Aggressive Campaign Strategy
Cloobeck’s early and ample investment in advertising is drawing attention, particularly given the timing. A campaign advisor confirmed the ad buy and a simultaneous social media push. Cloobeck himself emphasized his commitment to the state, stating in a text message, “I will always Fight for California. All Californians deserve the contract to be fulfilled for an affordable livable workable state. Watch [the ad] and you will see how a conservative Democrat fights for All Californians.”
This move follows former Vice President Kamala Harris’s decision last week to forgo a run for governor in 2026. Her withdrawal has created a wide-open race with a large number of candidates lacking importent name recognition. Democratic strategists suggest Cloobeck’s proactive advertising is a logical response to this landscape.
“It’s unprecedented for regular business. Not for this race,” noted Democratic media buyer Sheri Sadler, who is not affiliated with any current campaign.
Cloobeck’s aggressive approach isn’t new. He launched his gubernatorial bid in November promptly following the 2024 presidential election with a flurry of ads and billboards featuring his slogan, “California, Get a Cloo,” and the iconic California bear.
A Self-funded Campaign Fueled by Wealth and Connections
Cloobeck is heavily self-funding his campaign. He recently announced a further $10 million contribution, adding to the initial $3 million he invested. His wealth stems from a prosperous career in real estate and hospitality, notably as the founder of Diamond Resorts International, a timeshare and vacation property company he sold in 2016. He also gained public recognition appearing on the reality television show “Undercover Boss.”
While new to electoral politics,Cloobeck is a long-time and prolific Democratic donor and fundraiser. He maintains strong ties within the party, citing a close relationship with the late Senator Harry Reid, and his Beverly Hills home displays numerous photos with Democratic presidents and prominent political figures.
His financial resources were visibly on display at the California Democratic Party’s spring convention, where paid canvassers wearing shirts emblazoned with his name chanted his support. Cloobeck estimated at the time that the convention effort cost “probably a couple hundred thousand dollars.”
The challenge for all candidates, including Cloobeck, is raising their profile among California’s 22.9 million registered voters.Cloobeck is attempting to position himself as a “conservative democrat” appealing to a broad range of Californians. His advertising is likely aimed at defining that identity and differentiating himself from the growing field of contenders. The absence of a clear frontrunner, particularly after Harris’s decision, presents both an possibility and a challenge for Cloobeck to establish himself as a leading candidate.