NBA Hall of Famer Charles Barkley revealed to NFL legend Shannon Sharpe in a recent episode of the “Club Shay Shay” podcast how he lost $25 million gambling over the years.

Charles Barkley won a million dollars seven times, lost a million 25 times from gambling on $25,000 a hand

“I love to gamble, I don’t like to gamble,” Barkley told the NFL Hall of Fame tight end. “I would go to Vegas, and I’d win a million dollars.”

When Sharpe asked him how much he played per hand, Barkley said he played “$25,000 a hand” on his gambling nights.  

He preferred cash winnings. The 11-time NBA All-Star wasn’t interested in checks or wire transfers. This only motivated him to continue wagering. 

“There’s probably been seven times when I won a million dollars,” Barkley added.

“But there’s probably been 25 times when I’ve lost a million.”

Sir Charles admitted that he was obligated to quit gambling for two years because it was “getting out of hand.” 

The 1993 MVP noted that he could have had several paydays between $600,000 to $700,000, but he insisted on playing until he left with at least a million.

“We’ll be sitting there, I’ll be up, and my friends would be like, ‘Chuck, let’s go for the night’.

“And in my head I’m saying, ‘Nah, we’re not leaving this motherf—ker until I win a million dollars.”

Barkley doesn’t view his gambling as a problem, calls it a “bad habit”

Charles Barkley admitted that he felt exhilarated whenever he won, but his betting losses far exceeded his winnings.

“I got such a elation [when I won], but when I lost a million, I was so depressed. Because of the money, but [mainly] because of the losing,” he told Shannon Sharpe.

“I’d be depressed for a week [thinking], ‘Damn, I lost a million dollars?’

“I’d send the bill to my financial people and they’d be yelling and yelling and yelling.

“I was getting out [of] hand. No matter how good it feels winning, when you lose, it just f—king sucks.”

Barkley enjoyed gambling the most throughout the ‘80s and ‘90s, when he was close friends with fellow high-roller gambler Michael Jordan.

In 2021, former NBA All-Star Antoine Walker appeared on All Things Covered and told a story about the time he and Jordan almost lost a million dollars playing in a 36-hour game of spades.

Walker and Jordan were down $900,000, but the two still managed to get back all the money except $20,000.

In the end, Barkley doesn’t view gambling as an issue. 

“It’s not a problem,” Barkley said. “If you’re a drug addict or an alcoholic, those are problems. I gamble for too much money. As long as I can continue to do it, I don’t think it’s a problem.

“Do I think it’s a bad habit? Yes, I think it’s a bad habit. Am I going to continue to do it? Yes, I’m going to continue to do it.”

Charles Barkley, who is a current TNT analyst for Inside the NBA, has an estimated net worth of $60 million in 2024.