May 07, 2025

Coalition to Strengthen America's Healthcare

Hello and welcome back to The Best & The Brightest. I’m Leigh Ann Caldwell, back in the District after a quick trip to Los Angeles, where I made my Milken debut on a panel with fellow journalists about the future of the press and democracy. We had a lively discussion, and people told me later how refreshing it was to hear panelists express such pointed opinions openly—which is apparently a feature of the private, smaller sessions. (You can watch it here.) I had quite a few sidebar meetings with people letting me know their concerns about the economic situation. Tom Sullivan of Farmland LP, which invests in organic and regenerative farms, warned that credit for farmers is frozen because of market uncertainty, and that this could lead to food shortages at harvest time in late summer/early fall. And a representative from the U.S.-Mexico Foundation reached out to say they’re hopeful that the Trump administration will start to realize the importance of Mexico as a trading partner. (Good luck with that…) It was also great to hear how many people love Puck and make it part of their essential media diet. For those of you just checking us out, or still reading the small section in front of the paywall, it’s time to subscribe. You won’t regret it. Today, I’m taking advantage of my few days in California to write about the state’s politics and its sleepy-yet-crowded gubernatorial race. (Incumbent Gavin Newsom is termed out.) I’m particularly interested in Steve Cloobeck, a wealthy real estate developer with a long résumé, pithy catchphrases, and low name ID. In any other political year, his candidacy would likely be written off. But these days, people just aren’t sure what sticks with voters. California’s challenge-riddled economy is the fourth-largest in the world. Could that translate into Cloobeckmentum? Crazier things have happened.

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But first…

Texas twang: Sen. John Cornyn announced the senior staff for his reelection campaign today in a seemingly run-of-the-mill press release. But a closer look reveals some of the hires to be symbolically significant, as Cornyn gears up for a nasty and personal primary against Texas Attorney General Ken Paxton.Cornyn’s pollster, for instance, will be Tony Fabrizio, Trump’s campaign pollster and trusted advisor. That could be read as something of a slight to Paxton: Fabrizio had actually conducted a poll for a political group supporting Paxton earlier this spring, which showed Paxton beating Cornyn in the primary, but then struggling to win in the general election against a generic Democrat (the part of the poll that Paxton failed to release but sources told me about). In Texas, mind you.Paxton, who announced his candidacy against Cornyn in April and has had a less than stellar start to his campaign—as I chronicled in detail here—had hoped to notch Trump’s endorsement by now. But that hasn’t come, and it’s unclear that it will. Republicans, including Trump, are worried that Paxton, who is unpopular in the state, either can’t win a general, or would need hundreds of millions of Republican dollars to prevail—money Republicans would prefer not to waste on what should be an easy hold.But Cornyn, who is reviled by the Republican base in Texas, could have a tough time beating Paxton in the primary. In short, Republicans are annoyed at the cluster this race has become—especially when their top Senate recruit in Georgia, Gov. Brian Kemp, just backed out and they haven’t found a solid candidate yet in New Hampshire.
Lawler’s loss: President Trump endorsed New York Rep. Mike Lawler for reelection late last night, which would normally be welcome news for an incumbent, except that Lawler hasn’t decided yet—or at least announced—if he’s running for reelection or for governor. Lawler represents one of the three Republican congressional districts that Kamala Harris won in 2024. He’s been planning to run for governor, but then Rep. Elise Stefanik went public with her own interest in the job. Speaker Mike Johnson said he has spoken to Lawler about staying in Congress, and now it looks like Trump is putting the public screws to him too.

Now for the main event…

Kamala vs. … Cloobeck?

As the Democrats stumble out of the wilderness, California’s otherwise snoozy governor’s race might provide a test of voters’ patience for their own party’s version of the real estate developer turned reality star turned pol.

Leigh Ann Caldwell

A few weeks ago, I received an email from a guy named Stephen Cloobeck, asking to chat. Cloobeck? The name sounded familiar, but I had to Google him to find out that he wasn’t some former high school classmate or colleague, but rather a sixtysomething real estate mogul running for governor of California. Cloobeck has been fantastically successful, building and selling multiple hospitality businesses, and here he was, emailing a reporter himself rather than outsourcing that routine task to a comms guy. Now, I know a lot more about him. In short: Cloobeck is wealthy, hates over-regulation, thinks California is being mismanaged—and he’s a Democrat who is very wired up with other Dems, and leans hard into calling his home state “the country of California.” Anyway, I was happy to take the call. Despite the seven Democrats and two Republicans who have already announced their candidacies, the race to replace California’s term-limited Governor Gavin Newsom in 2026 is kind of a snooze. Even though California is the world’s fourth-largest economy and still reeling from the Los Angeles fires, the race is relatively frozen while everyone waits to see whether former Vice President Kamala Harris will decide to jump in, in which case conventional wisdom suggests she’ll mostly clear the field. (Politico has reported that Harris will make a decision by the end of summer. Meanwhile, as my partner Lauren Sherman noted in Puck’s Line Sheet, she looked great at the Met Gala last night.)

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The other Democratic candidates include Xavier Becerra, who was a congressman and Biden’s Health and Human Services secretary; Antonio Villaraigosa, the former mayor of Los Angeles; Katie Porter, who represented Orange County in the House, and just came off a Senate race; Betty Yee, the vice chair of the state’s Democratic Party; Tony Thurmond, the state superintendent of public instruction; Eleni Kounalakis, the current Lt. Governor; and former president pro tempore of the state Senate Toni Atkins. The Republicans running are Riverside County Sheriff Chad Bianco and Steve Hilton, a former Fox News contributor. “I’ve done so much polling and there’s no differentiation between the candidates,” said Mike Madrid, one of Cloobeck’s senior advisors. (Harris, of course, would be a game changer.) And then there’s Cloobeck, who has a relationship with Harris. He told me that he hopes to debate her if she runs, and also that he would like to bring a glass bowl filled with puzzle pieces with words on them, in homage to the “word salad” criticism of Harris’s communication style during her presidential campaign. That said, Cloobeck is a bit of a wordsmith, particularly when it comes to variations of his own name: “California get a cloo,” is part of his campaign slogan, and he’s said that he has an “incloosive” set of views on social issues, but adds that he doesn’t think transgender girls should play in girls’ sports. Anyway, we met for lunch at the Peninsula Hotel, where Cloobeck lived for two and a half years while his home was being built elsewhere in Beverly Hills. Cloobeck is rich—estimates suggest he has a net worth of around $100 million. He built Polo Towers, a high-rise time-share on the Las Vegas Strip, and then founded Diamond Resorts International, one of the largest time-share companies in the world, which he sold in 2016. And not unlike another developer-turned-politician, he was also a reality star—in his case, on the first season of Undercover Boss. (Trump’s show led to tears of sadness, his show led to tears of joy, he says.) He was clearly in his element at the hotel, where I ate a $58 salad while people stopped to greet him as “Gov” and he practiced his Spanish on the waitstaff. He’s dealt with Trump, too. In fact, he was in discussions with him to build Trump Tower in Las Vegas, but told me he couldn’t do it after meeting with him. Here, by his account, is where the superficial parallels end: “I have values, Trump has none,” he said. “I pay my contractors, Trump doesn’t.”

Dems in Distress

Cloobeck has donated millions to Democratic candidates over the years, and drops their names with ease. New York Sen. Kirsten Gillibrand wants to see him debate Trump, he said. He showed me a video that Sen. Cory Booker sent him, encouraging him to run and saying the party needs “fighters” like him. He was so close to the late Sen. Harry Reid that he called him “Dad.” He helped Reid defeat the plan to build the Yucca Mountain nuclear waste repository in Nevada and worked to get the Las Vegas airport’s name changed to Harry Reid International. When Cloobeck contemplated a run for governor of Nevada in 2018, Reid called him and Steve Sisolak into his office. Reid decided Sisolak would run and instructed Cloobeck to continue helping the party behind the scenes. He ended up back in Los Angeles, ultimately, with his eyes on a different seat. Cloobeck loves California, but he says the state is broken—it’s overregulated, overpriced, and underperforming. His campaign motto is “Making California affordable, livable, and workable,” a phrase he trademarked. He told me that he wants to streamline the more than 380,000 regulations that he says strangle the state’s development and growth. “I think the most difficult state-country to operate in is the country of California,” he declared during a Milken Conference panel this week about the state’s affordable housing crisis.

Whether or not Harris decides to run—and several California Democrats told me that nobody has any idea—Cloobeck’s deep ties to Democrats could come in handy. Heather Podesta, the influential Democrat who owns a large bipartisan lobbying firm, told me that Cloobeck “amuses” her, and that she sent him a $1 campaign donation when he announced so that “I can tell people I support you.” On the other hand, he could become one of the many rich Californians with political pipe dreams who have run and lost—William Roth in the ’70s, Al Checchi in the ’90s, Meg Whitman in the 2010s, etcetera. Plus, a messy lawsuit with his ex-girlfriend, an OnlyFans model (which, as Cloobeck himself pointed out to me, my partner Bill Cohan wrote about for Vanity Fair in 2021), could become a liability. Meanwhile, as the Democratic Party searches for a way out of the wilderness, would California Dems really support a wealthy real estate developer who has never run for office? Sure, similar characters, like Rick Caruso, have found degrees of political success in the state. But this archetype is almost diametrically opposed to the candidate model being pushed by Senator Bernie Sanders and Rep. Alexandria Ocasio-Cortez, who have traveled the country railing against billionaires and the oligarchy, spreading a populist message that workers have been forgotten, and riling up a base that’s craving Democrats with a spine who will say something—anything.

A Post-Partisan Petri Dish?

Cloobeck, who calls himself a political “unicorn” because of his uber-centrist sensibilities, is betting that Californians care less about traditional partisan divides than about fixing the state’s massive problems. He says many of his donors are Republicans, and he’s hired one as a senior advisor: Mike Madrid, who was part of the anti-Trump Lincoln Project and specializes in the must-win Latino vote. Reed Galen, a Lincoln Project co-founder and a Californian, texted me that Cloobeck is “serious about the race” and “has a chance to be a wild card.” Moreover, “he’s friends with everyone, and is definitely underestimated by the sclerotic, hidebound political class.” This being California, Bill Burton, a top former aide to President Barack Obama who has called California home for nearly a decade, told me he’ll have “no chance” if he runs like a traditional, more centrist member of the party. “If he has some big ideas about how to really knock down barriers to the housing crisis and homelessness,” Burton said, then he has a shot. There’s an argument to be made that whatever direction the national Democratic Party goes—toward an A.O.C.-like populist, or an anti-Trump capitalist like Illinois Gov. J.B. Pritzker, or a centrist red-state Democrat like Andy Beshear, or a blue-state podcaster like… Newsom—it won’t apply in California, a state that, Newsom aside, feels mostly divorced from the national party discussion. It’s an overwhelmingly blue state, where state politics are dominated by the still mostly progressive city of San Francisco. People just aren’t paying attention the same way in Southern California—as one Democratic operative put it, they don’t think too much about politics or their candidates and just elect the person with the highest name ID. Madrid told me that when he looked into the crowded race, none of the current candidates appeared to have a particular advantage at this point. Sensing the void, Cloobeck is building a media infrastructure that will, as seems to be the fashion these days, include his own podcast. Cloobeck claims not to want consultants to tell him what to do or say—in his case, he told Madrid, for the practical reason that he is dyslexic and can’t follow a script. After meeting him, it feels very unlikely that Cloobeck will allow himself to be molded to fit a consultant’s vision. “This can be a complete train wreck or remarkable success,” Madrid told me. “We are going to test the theory of the case.”

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