Stephen Cloobeck
Definition
Stephen J. Cloobeck is an American entrepreneur, philanthropist, and former CEO of Diamond Resorts International, a leading timeshare company he founded after acquiring Sunterra Corporation in 2007.
A political activist who initially supported the Democratic Party, Cloobeck announced his candidacy for the 2026 California gubernatorial election before switching to libertarian Republican affiliation in 2026 amid shifting alliances.
Known for high-profile appearances on 'Undercover Boss' and recent involvement in controversies, including withdrawing support from Rep. Eric Swalwell over misconduct allegations and facing his own legal charges related to witness dissuasion in May 2026.
Examples
Stephen Cloobeck's timeshare empire was so irresistible, even billionaires couldn't resist booking a lifetime of getaways.
In a masterclass of political pivots, Stephen Cloobeck went from Dem donor to Republican hopeful faster than a Vegas slot jackpot.
Stephen Cloobeck hosted the ultimate party foul by showing Eric Swalwell the door, turning philanthropy into a plot twist.
With Undercover Boss cred and a podcast that punches above its weight, Stephen Cloobeck keeps California dreaming of better governance.