13. Charles Barkley
Location: Blackjack game
Initial cost: N/A
Amount added: $25,000*
Charles Barkley is unforgettable in the NBA world, adored and detested in equal measure. Even retired, his presence leaves a lasting mark, especially if you’re fortunate enough to encounter his generous side.
In 2014, Barkley shared with Conan O’Brien his firm belief in generous tipping by successful individuals. He recounted a memorable occasion where, after a $700,000 blackjack win, he graciously tipped the dealer $25,000, a gesture he later felt could have been even more generous.