Let’s talk Charles Barkley—but don’t get it twisted, this isn’t about basketball. Nope, we’re diving into a different arena Chuck’s grown to love post-retirement: golf. And here’s where it gets even more interesting—sports betting is in the mix now. If you’ve seen his old swing, you know it was… let’s just say, tough to watch. Chaotic pauses, jerky stops—it looked like his body was buffering in real time. But that was then. These days? Chuck’s swing is smoother, his game’s tighter, and with betting involved, he might just surprise you.
And speaking of surprises, Charles Barkley is teeing it up once again at the American Century Championship, and he has successfully failed in his fight against his gambling ‘addiction’. “I love gambling,” he once said. But after his losses piled up, and he hit a breaking point, he stopped indulging in the game of fortune for two years. But the itch came back strong. His friends called him a “f—– idiot” for not walking away after winning hundreds of thousands. “In my head, I’m saying, ‘No, we not leaving this MF until I win a million dollars,’” he admitted. Winning wasn’t enough—he wanted to dominate, and that mindset has him right back at the tables.
For the fifth year in a row, Caesars Sportsbook has set a prop bet on whether Barkley can finish in the top 65. Last year, he surprised everyone by landing 58th, easily beating the top-70 line. So the question is—do you trust Chuck to do it again? Well, Barkley certainly does. While chatting on SiriusXM PGA TOUR Radio, he didn’t waste a second when he heard about the bet. “Vegas got me at 65?” he said, genuinely surprised. And then came the offer: “Whatever you want to bet, whatever you want to bet… and make it light on yourself.” But Chuck wasn’t done—he raised the stakes himself. “I should be in the top 50. I should be even lower than that. I’m gonna play better than next year, I got you…”
“Vegas got me at 65?!”
Never afraid of a friendly wager, Charles Barkley is counting on himself at this week’s @ACChampionship. He talks about it with Colt & Drew on Gravy & The Sleeze.@ColtKnost | @thesleezyman
: https://t.co/NmEfdRUvZs pic.twitter.com/kqjzhmavTT
— SiriusXM PGA TOUR Radio (@SiriusXMPGATOUR) July 9, 2025
The podcast hosts weren’t about to let that moment pass. “Well, I’ll take you right now. Man, we can just bet right now before the line comes out, I’ll take you outside the top fifty,” one of them said. Without skipping a beat, Barkley fired back, “Let’s go 55.” And just like that, the bet was locked in. With a laugh and that signature Barkley flair, he sealed it: “I’ll take 55 right now, little man.”
Charles Barkley doesn’t just like to gamble—he lives for the thrill of it. He proudly recalled how he stayed up all night in Vegas, unable to pull himself away from the tables. “It is exciting,” he said. That excitement, though, has come at a cost. Barkley’s been candid over the years about the double-edged sword of his love for betting. On the Club Shay Shay podcast, he admitted, “There’s probably been seven times that I won a million dollars, but there’s probably been 25 times I’ve lost a million.” That’s not just pocket change—that’s roughly $25 million, he says he’s lost to gambling.
And yet, even when Barkley tried to quit, the addiction pulled him back in. “I got such elation [by winning], but then when I would lose a million, I was so depressed … No matter how good it feels winning, when you lose, it just f—— sucks,” he confessed. Barkley’s gambling highs were real—he once walked away with $5 million in one night. But so were the lows, like the time he owed a Vegas casino $400,000. And still, despite it all, Barkley isn’t ready to walk away from the action entirely. In fact, he’s even open to owning a casino in Birmingham. “Hell yeah, I would love to be part of it,” he said.
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