Despite working as an analyst for TNT since 2000, Charles Barkley hasn’t picked up all the tricks yet, especially when it comes to predicitions. The Hall of Famer routinely shoots himself in the foot with his ‘guarantees’, which are infamous for not coming through.
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Barkley shared another parlay for last night’s contest between the Denver Nuggets and the Milwaukee Bucks, much to the amusement of his co-hosts. Ernie Johnson, on his part, pulled Chuck’s leg by joking that the last time he won a bet, Gone With the Wind was the top movie in the country.
Unfazed by the digs, Sir Charles revealed his wager for the game, which came incredibly close to hitting for once. He bet that Nikola Jokic and Giannis Antetokounmpo would grab 12+ rebounds while Jamal Murray and Damian Lillard would score 20+ points. Kenny Smith immediately weighed in on the odds of that happening.
“You know what I think is gonna be the toughest one?” Smith said. “Antetokounmpo with the 12 rebounds.”
Barkley, however, maintained his faith in the Greek Freak, arguing that he would grab 15 boards. Instead, the two-time MVP went off for a season-high 19 boards against the Denver Nuggets, easily proving Smith wrong. The Joker also fulfilled his leg of the parlay by corralling 15 rebounds in the game.
However, the point guards missed their marks by a couple of points, failing Chuck.
The Fellas take a look at the state of the world the last time Chuck won a bet 👀😆 pic.twitter.com/wG79S5ifJJ
— NBA on TNT (@NBAonTNT) February 28, 2025
Murray ended the night with 20 points, and Lillard with 19. One more field goal or trip to the free-throw line would have pushed both of them to 21 points, securing Barkley’s first successful bet of the 21st century.
As close as he came to tasting victory this time, Sir Charles must be happier losing on parlays over his old habit of losing in casinos.
Barkley lost $25 million in Las Vegas
Over the past two decades, Barkley has endeared the basketball community with his charming uncle persona and family-first values. However, during his playing days, the 1993 NBA MVP was a hothead with more than a few bad habits.
The 6’6” forward needed an otherworldly confidence to battle 7-footers in the paint and routinely grab rebounds over them. Unfortunately, that confidence also spelt trouble for him when he took it to the casinos of Nevada.
“There’s probably been seven times that I won a million dollars. But there’s probably been 25 times I’ve lost a million,” Barkley admitted on Shannon Sharpe’s podcast last year.
As a superstar in the NBA, Chuck certainly had the money to blow. But as the losses piled up, he realized that he was mortgaging his future every time he stepped inside a casino.
“I had to change my mentality because you can never break the casino, [but] they can break your a**,” Barkley reflected.
Today, Barkley’s poor luck with bets continues to haunt him. But at least at TNT, he’s earning $21 million a year — even when his parlays don’t convert.
