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What can Charles Barkley do wrong? An NBA icon who transcended into a broadcasting career and earns more than $21 million per year. Yet, when it comes to prediction, the former TNT analyst often ends up on the losing side. Just last season, he won a parlay on the final episode of ‘Inside the NBA’. These vices and being wrong with his predictions have caused him enough damage, as he calls himself a ‘degener—— gambl—’. Because of this, he needed a stern reality check from his close friends.

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“So I love gambl—-, but I became a total crazy person because I won a million dollars probably 10 times. I’ve lost a million dollars probably 30 times. So every time I went to Vegas, I’d be up 300, 400, $500,000. My friends would be like, ‘Dude, you got to quit. We up. Let’s go. Let’s go get drunk and have some fun.'” Despite earning close to half a million dollars, the 11x All-Star wouldn’t quit. He wanted to chase the ‘million mark’ and often ended up losing more. That’s why he even stopped gambl—- for 2 years until he had an honest conversation with his friend.

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We like to smoke ciga— and drink. I said, ‘Man, I sure miss Vegas, miss casinos,'” Charles Barkley said on ‘Pardon My Take’. His friends called out his behavior and explained why he was losing in the first place.  “He says, ‘Yo, man, gambl—- ain’t your problem. Being a f—– idiot is your problem.’ Explain. They’re like, ‘Dude, gambl—- is peaks and valleys. You’d be up 300 $400,000 like Chuck, let’s go get dru— for the night. Quit. But you want to get to the imaginary million. Then you lose that and then you lose the whole million credit line you got.‘” That led to Barkley stop chasing the imaginary million and instead spend time with his friends even when he loses.

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Now he lives in Scottdale, and Charles Barkley claims he visits Vegas every two to three weeks with a new approach.  “Let’s win a couple hundred thousand. Enjoy watching all the games. We lose a couple hundred thousand. Let’s quit. Go drink. We play golf. And ‘I’m not going to be mad if I lose a couple hundred right now. When I lose a million, I’m depressed for like a week‘”.

His problem of addiction is not new. “Do I have a gambl—- problem? Yeah, I do have a gambl—- problem but I don’t consider it a problem because I can afford to gamb—. It’s just a stupid habit that I’ve got to get under control, because it’s just not a good thing to be broke after all of these years,” Barkley had said in 2006 in an interview with ESPN. But now limiting his losses to less than a million makes him enjoy the weekend even more. And that revelation was only possible after having an honest and brutal conversation with his friends.

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New and improved Charles Barkley is not afraid of losing to Shaquille O’Neal, Tom Brady, and Patrick Mahomes

As stated earlier, on TNT segments, the Chuckster rarely won. The host of Inside Show even reminded Barkley was his total wrong predictions on the show this past season. “You’re 0 and 17 on our preview show,” said Ernie Johnson. But that didn’t stop the 76ers icon from believing in his prediction and even had a bet with Shaquille O’Neal. Last year, he predicted that Miami would beat Boston by exactly 10 points, and Charles Barkley was confident and challenged his best friend. You can currently predict what happened next, unlike Chuck.

At halftime, they seemingly doubled their arrangement, and the Lakers legend was the eventual winner. No shocks there. To rub it in, Shaq used the stacks of dollars and mocked Barkley. Losing to multiple-time champions is not new for the TNT analyst. In fact, he has even lost $100,000 in nearly every Super Bowl because he was bet—— against Tom Brady and Patrick Mahomes. Charles Barkley even detailed his exact score of losses against Mahomes. “Adam, I have bet against Pat Mahomes like six straight games. This is true now. Last year against Buffalo, I thought they were gonna lose.”

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This year, he was finally able to get 1 against Mahomes and the Chiefs as they lost to Chuck’s favorite Eagles. Before the Super Bowl, he made a prediction: “Not only are the Eagles going to win. It’s gonna be a blowout… 34-17.” It was not this exact scoreline, but the Eagles fan in him would be proud to end the Chiefs’ chokehold on the NFL.

Disclaimer:
Gambl—- involves financial risk and can be addictive. If you or someone you know has a gambl—- problem, seek help from a qualified professional. Please gamble responsibly and only if you are of legal gambl—- age.

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Pranav Kotai

2,691 Articles

Pranav Kotai is an editor at EssentiallySports, specializing in basketball coverage with a focus on trade dynamics and front-office decision-making. Having previously worked on the Trade Desk vertical, he brought clarity to how salary cap pressures and roster needs shape NBA transactions. His insightful coverage of the Philadelphia 76ers’ decision to hold firm on Joel Embiid amid trade speculation highlights how market context and team strategy influence major roster moves. Before joining EssentiallySports, Pranav holds experience of skills in professional writing, editorial work, and digital content creation. He holds a postgraduate diploma in digital media from a reputed institute, where he mastered the tools to create engaging and credible content across various platforms. Known for his attention to detail, proficiency in storytelling, and editorial expertise, Pranav combines deep basketball knowledge with sharp analytical abilities to deliver clear, insightful perspectives on the complexities of NBA trades and team management.

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Tanay Sahai

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