Many celebrities and sports figures have been ruined by Vegas. Mike Tyson dumped most of his fortune at Steve Wynn private blackjack tables at the Golden Nugget. Dennis Rodham went broke at that time playing mountains of chips at the Hard Rock Vegas.
Nowadays you figure someone like Drake or Bruno Mars earns so much that he could never go under, but once the money stops coming it, ruin is certainly possible.
As far as Watanabe, from what some of the Caesars pit bosses have told me, he was prevert who would hit on the young male dealers with the crudest propositions. Yes, something like UNKewlJ with no bankroll. And Watanabe was actually playing, while UNKewlJ is just there for cover, mindlessly pushing some red and green chips around.
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