Better know a CA gubernatorial candidate: Stephen Cloobeck

Entrepreneur/philanthropist Stephen Cloobeck sports a little bit of the star quality some Californians seem to expect from their governors.

The 63 year old was the founder, chairman and CEO of Diamond Resorts International, a timeshare company of 92 leisure resorts and almost 400,000 owners that was purchased by Hilton Grand Vacations in 2022 for $1.9 billion. In that role, Cloobeck appeared on the CBS show “Undercover Boss” multiple times, something he touts on his campaign website.

On that site the Democrat says he’s spent the past 12 months focused on devising a plan to make California more “Affordable, Livable and Workable,” sentiments that echo the campaign pitch of Republican gubernatorial candidate Chad Bianco, the Riverside County sheriff. He says he’s held more than 250 meetings with state business leaders, politicians, venture capitals, union leaders, etc. on both sides of the aisle.

Cloobeck was raised in Encino and spent summers in Simi Valley, Sanger and Willits. His first business venture was in real estate. He built his first shopping center in Burbank in the 1980s, followed by others in Bakersfield, Hanford, Hemet, Buena Park and Mission Viejo.

He obtained a bio-psychology degree from Brandeis University and once wanted to become a heart surgeon. He also boasts some political appointments: by former U.S. Commerce Secretary Gary Locke to serve as the inaugural chairman of Brand USA Inc., a nonprofit corporation formed by the federal government to promote travel to the U.S., and by former Nevada Gov. Kenny C. Guinn to serve on that state’s Standing Committee on Judicial Ethics.

What’s going for him: On-camera charisma. You don’t get put onto a major channel’s show multiple times unless you got a certain “it” factor and Cloobeck seems to have it. He portrays himself well in interviews and seems to be trying to establish himself as a crossover candidate by taking Republican talking points about California being a “broken state.”

Indeed, his whole businessman persona looks not all that dissimilar to previous GOP gubernational candidates like John Cox or Meg Whitman.

He also has, it must be said, a rather snappy campaign slogan: “California Get a Cloo.”

What’s going against him: He’s a political outsider and it seems unlikely establishment Democrats –  and the deep-pocketed donors who support them – will coalesce around him instead of a more established politician like Xavier Becerra, Katie Porter or Antonio Villaraigosa, to name just a few of the Democratic brands that he’s running against.