News Summary

• Drake is only the loudest name in a tradition that stretches back decades.
• Long before betting moved onto phones and streaming platforms, A-listers were quietly building reputations at the felt.
• Charles Barkley has spoken openly, and often with a laugh, about the eye-watering sums he has run through over the years.
• For these stars, the wager became part of the brand, a way of signaling that they play as hard off the clock as they do on the table.