Sports BettingCasinoBeats · Sep 1
Undercover Boss Stephen Cloobeck Exposed for Betting on Himself to Win California Governor Race At Kalshi
By Adam Roarty•September 1, 2026
The brief
Stephen Cloobeck was the first head of a company to appear twice in Undercover Boss. The founder of hotel group Diamond Resorts has now been exposed for wagering on himself to win the California gubernatorial race at Kalshi. Kalshi announced enforcement action against Cloobeck on Monday, along with two other political…
Original report
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