There is no shortage of Charles Barkley gambling stories. However, most of them have focused on his losses, just as basketball fans and pundits have fixated on his failures that overshadow his Hall of Fame NBA career.
Speaking on CONAN on TBS in 2014, Barkley talked about a huge gambling win for a change — $700,000 at a blackjack table, to be exact.
Barkley has won even more money than this on other nights. But no matter how you look at it, winning $700,000 in one seating is still jaw-dropping, even for some rich like Barkley, who made over $40 million during his career.
This was an unforgettable experience for a self-proclaimed gambling addict like him — even more so for the dealer he tipped $25,000.
"I probably should have tipped more," he admitted.
Barkley once shared how he cashed in $700,000 at blackjack during a wild weekend in Las Vegas in February 2007. In that same weekend, he also hit a massive payout on the Indianapolis Colts' Super Bowl victory over the Chicago Bears.
Barkley didn't specify whether the $700,000 score he referenced earlier came from that particular weekend or from another one of his many high-stakes gambling sprees. Regardless of when or where it happened, luck was clearly on Barkley's side that night. And that would not have happened without the blackjack dealer. So, he thought he should share some of his spoils and tipped $25,000.
With this kind gesture, Barkley ironically broke his personal rule of always tipping employees 20 percent. Though $25k was huge, it was only approximately 3.57 percent of his winnings. It was far below 20 percent, which meant a tip of around $140,000.
To be fair, that would have been excessive, since standard casino tips are only around 5- 10 percent . Still, applied to Barkley's case, that would be $35k to $100k, meaning that he still fell short of staying true to his code.
Still, Barkley had no choice. The millions of losses he's incurred through the decades flash before his eyes. It was only mandatory for him to tip that much.
"I thought that was pretty generous," he explained. "Because when you lose money, they don't give you any back."
Barkley always tips 20 percent to service workers — nothing more and nothing less. He believes that the small amount could make the difference between surviving the day and living on the streets. So, he follows this rule and highly encourages his rich peers to do the same .
"The waiters, the waitresses, the blackjack dealers, they work extremely hard. They don't get a great salary," he said . "The more successful you are, the more you should tip.
However, as his anecdote shows, some rules don't apply to gambling.
In love with the rush of the game, Barkley has lost millions of dollars to casinos and sports betting. He has gambled away $25 million , once losing $2.5 million in just six hours , before his friends stepped in to help him.
For most people, losing thousands, let alone millions, due to gambling is a tell-tale sign that they have lost control. But not Barkley because he believes that he has earned the right to such reckless abandon.
And the less fortunate and people who work minimum-wage jobs will always get a small cut from Barkley's hard-earned, hard-gambled wealth through tips. Blackjack dealers, however, can only expect less than 20 percent from the NBA legend.
This story was originally published by Basketball Network on Mar 1, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.
