Who Is Stephen Cloobeck?
And in this corner we have Stephen Cloobeck, a real estate and hospitality tycoon who earned his fortune through the timeshare company he founded (and then sold for $2.2 billion), Diamond Resorts. You might recognize him from his two appearances on Undercover Boss (the show where out-of-touch CEOs rub elbows with the commoners who work for them) or from his appearance on MSNBC, during which he railed against the Democratic Party for criticizing rich people.
Nevertheless, he's also a huge Democrat donor who's written out million-dollar checks for Hillary Clinton, and counts among his contacts the likes of Chuck Schumer, Nancy Pelosi, Pete Buttigieg, and Cory Booker. He's played golf with Bill Clinton and Barack Obama. He was even the chairman and CEO of Brand USA, the country’s official tourism bureau, under Obama.
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