(Inside California Politics) — California gubernatorial candidate Stephen J. Cloobeck (D) is out with new television advertisements targeting President Donald Trump. The hospitality businessman and former CEO of Diamond Resorts joined Inside California Politics this week as campaigns for the state’s highest office.
Cloobeck’s advertisements label President Trump as a cheater, referencing the ongoing effort to redraw congressional districts in Texas to pick up more GOP seats ahead of the 2026 election. Another ad highlights President Trump’s friendship with the late convicted sex trafficker Jeffrey Epstein. An LA Times report published last week says Cloobeck spent $1.4 million on the messaging.
Cloobeck explained his strategy to host Nikki Laurenzo and said he’s drawing a clear distinction between himself and other candidates by making clear he has personally pushed back against President Trump.
“I have sat across the table from Donald when he was looking to build the Las Vegas tower. Our architect was the same,” Cloobeck said. “I came away saying, ‘I cannot work with this man.’ We have different morals, ethics, philosophies of integrity. So I passed, and the architect was not happy with me. But I’ve never sold my soul for money. And I studied how [Trump] was trained with Roy Cohn’s philosophies of lie, deny, lie, deny. I don’t live that life, I live with integrity. California needs a fighter. And out of all the candidates that exist today, there’s not one who sat across the table from Donald Trump that said no.”
When pushed on whether former California Attorney General and HHS Secretary Xavier Becerra would disagree with that notion, Cloobeck said Becerra challenged Trump “with other people’s money, not his own.” Becerra sued the Trump administration over 100 times in his role as the state’s chief law enforcement officer.
“I mean, [Becerra] has never signed the front of a check. I love him, he’s a nice man. But, Xavier who? I mean, look, really. He’s never signed the front of a check, he’s never fixed broken,” Cloobeck said.
Homeowners’ Insurance Crisis
Cloobeck also highlighted what he claims is a solution to California’s homeowners’ insurance crisis — a plan that involves regulatory modernization, wildfire mitigation efforts, public-private partnerships and strengthening consumer protections. Cloobeck’s campaign website says he will convene a statewide Home Insurance Summit on his first day in office, if elected.
“I’m treating every single person in California as a customer because we are customers California,” Cloobeck said. “If you look at all the other candidates, which other candidate has ever been in the consumer business and treated people like customers?”