Charles Barkley enjoys his fair share of gambling, and it's one of the reasons he and Michael Jordan got along so well. In addition to the fact that the duo got along well and enjoyed gambling, the pair enjoy playing golf as well. Although they're no longer close, Barkley still enjoys both golfing and gambling when his schedule permits.
At one point in 2015, the Hall of Famer opened up on his gambling habits, admitting that he took two years off from gambling. Around that time, he spoke in an interview where he admitted that he went to Vegas on several occasions and left with a million dollars.
However, with that being said, Barkley admitted to losing a million dollars in one trip to Vegas on several occasions. As a result, he's had to teach himself how to both quit while he's ahead and have his fair share of fun while doing so in moderation.
In 2021, Charles Barkley joked with GOLF.com that he wanted to die broke so that his family didn't inherit his massive fortune:
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“Listen, everybody knows I like to gamble. I wanna be dead broke when I keel over, Phil. I don’t want to leave all that money for my free-loading family. I’ve been taking care of them my whole life. I wanna be dead broke at my last breath.”
Charles Barkley's gambling losses
Going back to the 80s, Barkley frequently gambled. While it didn't impact his basketball career, it sounds as though the Hall of Famer had to learn to gamble responsibly.
During an appearance on "In Depth with Graham Bensinger" in 2020, the Hall of Famer spoke about how he was able to change his gambling mindset:
"It's exciting to win money. You know, I hear all these people talking about, 'You just like the action,' no I like the money actually and it always sucks when you lose but it's a great feeling when you win.
"I think the thing that I conquered about my gambling was I changed my mentality — I'm not trying to win a lot, I'm just trying to win. You know, Graham, I've won a million dollars probably four or five times in a single day. But I've lost a lot more millions in a single day."
With Charles Barkley recently agreeing to a 10-year extension with TNT worth upwards of $100 million, it's safe to say he likely won't die broke.