It’s been years since Charles Barkley played in the NBA, yet people still consider him one of the best basketball players in the world. Between his incredible skills as a power forward, his willingness to say what was on his mind, and his gregarious smile, Barkley was someone even non-basketball fans rooted for.

Sadly, as wonderful as Barkley was on the court, his personal life has always been a mess. Most of his fans are familiar with his gambling struggles, but it turns out that those are only part of the equation that makes up Barkley’s dark past.

Charles Barkley’s struggles with gambling

Unlike some athletes who try to hide their less desirable quirks from the public, Charles Barkley has always been upfront about the fact that he enjoys gambling. He’s also willing to admit that over the years, he estimates that his love of gambling has cost him around $20-$30 million.

“I’ve won a million dollars probably four or five times in a single day,” Barkley told the Basketball Network. “I’ve lost a lot more millions in a single day. I’ve lost a million dollars at least 10 to 15, somewhere in there. I probably only won a million five or six times, but I’ve lost somewhere between 10 and 20, I can’t get an exact number because we are going back to the ’80s.”

While it’s easy to hear that amount and assume Barkley has a gambling problem, he claims he doesn’t. The former NBA player says the amount he’s lost has less to do with the amount of gambling he does and more to do with the way he gambles. Before he took a break from the casinos for a few years, Barkley explained he was an aggressive gambler who always had the goal of winning a million dollars whenever he entered a casino.

“It got out of hand, but I quit for two years, and I remember talking to my friends who said, ‘Gambling is not your problem; you’re just an idiot. We’ve sat on a table with you, and you were up 300, 400, 500, 600 thousand dollars,’ and they said, ‘Let’s quit.’ I developed this thing where I have to win a million dollars.”

While Barkley’s gambling losses are shocking, there’s no evidence that he’s even gotten in over his head.

Barkley’s fighting past

With his effervescent smile and larger-than-life personality, Barkley seems like the kind of guy it would be fun to go out for a beer with. Some point out, however, that there was a time when this would have not been fun.

Back in 1997, Charles Barkley threw a man through a bar window, as the South Florida Sun-Sentinal reported. The act, Barkley claims, was the result of provocation. Police arrested Barkley, and his teammate and friend Clyde Drexler bailed him out.

It’s worth noting this wasn’t the first or last time Barkley got involved in a fight. He has a history of using his fists. It’s also not the first time his temper resulted in an arrest. He stated he doesn’t even know how many times he’s been arrested. One of the most interesting things about Barkley’s fighting history is that he’s found not guilty of the charges in most cases.

Barkley charged with DUI

In 2008, Charles Barkley was pulled over after he ran a red light in front of a police officer. His excuse for the traffic infraction was that he was desperate for oral sex. The explanation would’ve been enough to generate news stories. But things took a turn for the worse when the officer determined Barkley was drunk.

This time, Barkley wasn’t able to skirt the charges. He pled guilty and received a five-day jail sentence. While it appears that Barkley has settled down a bit, based on his past, his future will likely be anything but boring.