Online Casino Gambling with Sir Charles: Barkley’s Wild Wagers

It can be absolutely delightful to hear about famous gamblers winning big in the online casino gaming scene.

It’s not unlike rooting for our favorite athletes on the sporting field. When we imagine our heroes doing well, we feel like part of the success if ours too!

It can be less comfortable, though, to watch an A-lister struggle with gambling. And that is definitely the case with one of the greatest basketball players of all time Charles Barkley, who is also a beloved media personality.

He may, in fact, be the least successful celebrity gambler of all time!

Want to know more about his gambling story? Read on!

Early Life and NBA Career

Like the greatest ever to play the game – and notable fellow gambler Michael Jordan – Charles Barkley didn’t come to major attention as a basketball player until relatively late in his pre-professional career.

As a high school junior in Leeds, Alabama, where he grew up, Sir Charles didn’t even make the varsity team!

Over the summer, however, his height shot up six inches, and standing at 6’4” (1.93 m), he went on to great success at the high school and collegiate levels.

This success came despite an atypical physical stature… to put it politely. Barkley was always much stockier than his teammates, and this earned him some colorful nicknames: “the Crisco Kid” was one, and “the Round Mound of Rebound” an even more memorable moniker.

In 1984, he was drafted by the Philadelphia 76ers, where he played alongside legends Julius Erving aka Dr. J., Moses Malone, and Maurice Cheeks. In 8 seasons there, he became a household name and perennial All-Star. This was followed by four seasons with the Phoenix Suns, then three with the Houston Rockets.

He was also a part of the “Dream Team” at the 1992 Olympic Games in Barcelona.

TV appearances

Though not quite as famous as his MJ or Larry Bird, he was nonetheless a national celebrity during the 1980s and 1990s. You might recognize him from the 1996 cult classic Space Jam.

He was also a frequent advertising spokesman, appearing in ads for McDonalds, Capital One, Taco Bell, Draftkings, memorably for deodorant company Right Guard, and, of course, Nike, where he had his own line of shoes.

And of course, Barkley has been a notable basketball analyst since 2002, appearing both on TNT and CBS and discussing both NBA and NCAA games.

Gambling Rollercoaster

With a bio like that, you can bet that Sir Charles amassed a pretty significant bankroll with which to play.

And throughout a volatile gambling career, he has taken full advantage of it!

The scale of his bankroll (mis)management is almost impossible for mere mortals to imagine. In one 2016 interview, he stated that he has lost over $1 million on between 10-20 separate occasions!

Let that sink in. The first nine times he lost more than $1,000,000, he decided it was fine to continue with his behavior unchanged.

But as the big man himself has said, he can afford it:

“It’s a stupid, bad habit. I have a problem… But the problem is when you can’t afford it. I can afford to gamble. I didn’t kill myself when I lost two and a half million dollars. I like to gamble and I’m not going to quit.”

For the record, that $2.5 million loss. came in one six-hour period in 2006. (For those following at home, that’s a loss rate of $415,000 per hour!)

With that said, the man has a point! A person earning $80,000 each year isn’t going to worry about dropping $60 once in a while, and a truly wealthy individual can afford losses that would be unimaginable for most of us.

With that said, Barkley’s net worth was estimated at a robust $50 million in 2021… so lifetime gambling losses of $30 million (his most recent estimation) are more than a drop in the bucket.

It’s not as though he always loses, however!

For example, he won a handsome $750,000 betting on the Patriots in their 2003 NFL championship season.

He claims to have won over $1 million at least ten different times in his life!

Sued by the Wynn

Generally speaking, casinos prefer not to take legal action against their guests… especially celebrities!

It’s not the image they like to project. And big time casinos will often to go significant pains to lure A-list celebs to their gaming floors, to help draw more players to the tables.

So you can rest assured that when legal action is taken, it’s because they house feels all other options have been exhausted.

That seems to have been the case when Barkley was sued by the Wynn Las Vegas for $400,000. They allege that he borrowed $100,000 on four occasions, and then refused to pay the piper.

In addition to the ugly PR, Barkley ended up paying the house the sum they demanded, in addition to $40,000 more in legal fees and court costs.

Turning Over a New Leaf?

Despite (or perhaps because of) his many losses, Sir Charles has been singing a different tune of late.

Give up gambling?

Don’t be silly!

His new betting philosophy is still an improvement upon his previous behavior, though. His new goal is to “lose hundreds of thousands, not millions.”

“If you do it in moderation it's alright … I love it. I love the action, I love the juice. But I just learned to do it in moderation. When I go to Vegas now, I try to win a couple hundred-thousand dollars. If I lose a couple hundred-thousand dollars, I quit and still have a good trip.”

We wish the legend nothing but the best in his future ventures, and hope his gambling habit doesn’t bring him to grief. From where we see it, Charles Barkley may well be the worst celebrity gambler of all time.