When Shannon Sharpe brought Charles Barkley on Club Shay Shay, it was no-holds-barred. He spilled on everything from his dysfunctional family to his brawls in the NBA. Most of his experiences came with profound life lessons. However, there was no lesson learned after losing millions. Chuck has a little habit of gambling. Especially sports betting. Like golf, he’s not the best at this either. Just like the Chuck Guarantee is failing the playoffs streak, Barkley has a history of putting his money on the wrong choice.

The result – he’s won a total of $7 million literally taking a gamble. But, he’s lost an eye-popping $20 million too. Does that deter Chuck? Not even the least. What was $20 million in sunk costs is now $25 million as of Chuck’s appearance on Club Shay Shay. And it could get bigger.

Sharpe asked Chuck if he’s “quenched” the urge to gamble after that loss. Barkley asserted, “I love to gamble. I don’t like to gamble,” which means he’s not quitting any time soon. He compared gambling to the stock market with “peaks and valleys.” He’s found a way to not get too competitive about it.

Unlike Shaquille O’Neal who visits Las Vegas for his multiple businesses and deejay shows, his TNT colleague goes to the regular gambling destination to indulge his habit. In those trips, he claims to have won about a million dollars seven times. But he’s lost a million dollars 25 times. He’s not quit now but he admitted to quitting in the past.

A good time dragged Chuck back into the gambling

Sir Charles usually goes to Vegas during the Super Bowl weekend to bet on the winning team. The way the Chuck Guarantee was wrong about the NHL playoffs as much as the 76ers today, Barkley has lost $100,000 a game betting against the Patriots or Chiefs. The previous year’s loss wouldn’t deter him from betting the next year.

However, Barkley told Shay he once quit gambling for two years. But he and his friends missed those trips. “I said, well, man, I was getting out of hand. They’re like, yo, man, you’re gambling ain’t getting out of hand. You just a idiot.” He of course asked his friends why he’s an idiot. They say because he tries too hard to earn a million and ends up losing just as much. They told him, “Why can’t you win $300,000 and say man we had a great weekend.”

They were convincing and that’s how Barkley returned to gambling with a new mentality. He’s into his long-running habit to hang out with his friends and play golf between gambling. It’s no longer about winning for Chuck.