Charles Barkley: Biggest Bets, Wins and Losses

Charles Barkley Biggest Bets

Credit: R24KBerg Flickr

One of the NBA’s most well known players, Charles Barkley is a legend of the game of basketball. He was an 11 time NBA All Star player, and the NBA’s most valuable player in 1993, not to mention a 2 x Olympic Gold Medallist, but one he retired, something else took his attention.


Barkley is well known for placing large sums of money of various different American sports (and casino games), as well as for how candidly he speaks about his gambling behaviour.

He has said in several interviews that he has won $1 million in a day 7 times, but he has lost $1 million in a day 15-20 times. In all, he estimates his lifetime losses to be somewhere in the region of $25 million, so while he may well be one of the highest stakes gamblers, he’s certainly not successful.

For Barkley, it’s not about the action, it’s about the winning. He loves to win, he loves the money, and he commits the cardinal sin of betting – he chases losses.

Or at least, he did.

He changed his mindset as he got older, playing to win small amounts rather than 7 figure sums, and stopping once he had achieved it. This means that Barkley is not the high stakes gambler he was in his younger days, but his exploits are still well known nevertheless.

Now a broadcaster for TNT, Charles Barkley is reportedly worth over $60 million today, so despite his huge losses over the years, he does at least seem to gamble within his means. It’s just that his means are significantly more than yours or mine.

That said, he often jokes that he wants to be flat broke when he passes away, so that his ‘free loading family’ don’t inherit any of his money, so maybe he is trying to gradually lose it all on purpose.

I’ve never been quite sure whether he was serious or not about that.

Charles Barkley's Biggest Bets

Charles Barkley Bets $550,000 on the Super Bowl Winning $1.5 Million

Bet: $500,000 (£353,336) - New England Patriots to Win the Super Bowl - Won

One of Barkley's first big wins post retirement came in 2002, and it is also one of his most famous, even after all these years. That's because he not only forked out a huge $500k stake, but he did so on one of the biggest underdogs in Super Bowl history.

He bet that the New England Patriots would beat the St Louis Rams in Super Bow XXXVI, then lumped on an additional $50k that they would do so outright.

Both bets won of course, netting Barkley somewhere in the region of $1,500,000, and establishing him as one of America's most famous gamblers. He is still occasionally asked about this bet in interviews today.