Charles Barkley has two things he’s proudly inconsistent at—golf and gambling. And he’s the first to admit it. While his Chuck Guarantee keeps missing playoff predictions, his bets haven’t been any luckier. The man once pulled off a $7 million win by risking it all, but don’t let that fool you. He’s also managed to lose a jaw-dropping $20 million along the way. Does that slow him down? Not even close. It almost feels like losing only fuels the fire.

Still, the fire hasn’t exactly burned out. In his recent sit-down with Shannon Sharpe on Club Shay Shay, Barkley casually updated that number to $25 million in losses. Yeah, five more down the drain. When Sharpe asked if he’d finally “quenched” the gambling thirst, Barkley doubled down instead: “I love to gamble. I don’t like to gamble.” It’s complicated, but he basically compares it to the stock market—“peaks and valleys.” Yet oddly enough, even with all that confidence, there’s one place Chuck refuses to place a bet—golf.

Barkley revealed this during an appearance on Sports Illustrated’s interview with Jimmy Traina. When Traina asked, “Did you win any money on the Masters… did you have Rory to win it on Sunday?” Chuck didn’t hesitate, “No, I don’t bet on golf.” It wasn’t hesitation. It was policy.

So what’s the one line even Chuck won’t cross? Turns out, it’s the first tee. Barkley cleared it up himself. “I love to gamble, obviously, but the chance of you picking who’s gonna win a golf tournament is like you know needle in a haystack.” Fair enough. Even Chuck knows when the odds are too ridiculous to bother.

Of course, skipping golf bets hasn’t stopped him from walking into casinos with a smile and a wallet on fire. That’s unlike Shaquille O’Neal, who’s there for work, not wagers. Charles Barkley? He goes to play. Sure, he claims to have won a million dollars seven times, but he’s also lost that much 25 times. He may not be quitting the habit, but when it comes to golf? Fear finally made him fold.

A good time dragged Chuck back into the gambling

It’s no secret Sir Charles loves his trips to Vegas—especially around the Super Bowl weekend. That’s when he bets big, and usually against the Patriots or Chiefs. But just like his Chuck Guarantee, those bets don’t always land. In fact, Barkley once admitted he’s dropped $100,000 on a single game and still came back for more the following year. The losses might sting, but they’ve never been strong enough to keep him away from the action.

Still, there was a time Charles Barkley actually stepped away. During his chat with Shannon Sharpe, he revealed, “I quit gambling for two years.” But even that break had its limits. According to Chuck, it wasn’t just him who missed the chaos—it was the boys, too.

“They’re like, yo, man, your gambling ain’t getting out of hand. You just a idiot.” Barkley laughed it off, especially after they told him, “Why can’t you win $300,000 and say, man, we had a great weekend.”

Eventually, their logic worked. Chuck’s back at it—but this time, with a different mindset. He’s not there to chase millions anymore. These days, it’s about golf, laughs, and good company. In his words, “we had a great weekend” is enough reason to roll the dice again.

Charles Barkley has wagered millions on blackjack hands and Super Bowl outcomes, often chasing the elusive million-dollar win. Yet, when it comes to golf, even the allure of a Masters Sunday can’t tempt him. His refusal to bet on Rory McIlroy is more about recognizing a line he won’t cross. In a world where he’s lost $25 million chasing highs, Barkley knows that some games are better left unplayed