Devastated by Man-Crush Tom Brady’s Triumph, Charles Barkley Revisits Worst Gambling Loss

It’s a loss that Charles Barkley is not getting over anytime soon. The NBA-pro-turned-broadcaster is a well-known sports gambler. But he’s not the best. Some of his bets were miscalculated and have incurred shocking losses. He’s gotten over most but not the one Tom Brady served him in 2016. Chuck has recalled this story a few times before and he did it again during his appearance on the podcast, SI Media with Jimmy Traina.

Two epic moments in sports history run parallel against each other. One is Tom Brady staging the biggest and best Super Bowl comeback in the history of the NFL. The other is the gambling loss that victory caused Charles Barkley.

Charles Barkley suffered expensive loss in Super Bowl LI

While on the Sports Illustrated podcast, Jimmy Traina asked Charles Barkley about his experiences gambling on sports. The host wanted to know which was the NBA legend’s “worst gambling loss” not by money, but by the devastation it caused Sir Charles.

The Philadelphia 76ers legend revealed that only the 2016 Super Bowl fit the bill.

Barkley has narrated this incident time and again and his emotions are still raw. Notorious for betting on sports teams, Barkley has an annual Super Bowl tradition to travel to Las Vegas. He did so in 2016 too.

The Atlanta Falcons were up against the New England Patriots in Super Bowl LI. Despite fawning over Tom Brady, Barkley had his money on the Falcons. NFL fans will recall this saga. By Halftime, the Falcons had a 28-3 lead and Barkley was comfortable.

“I was feeling myself. I was feeling no pain. The tequila was flowing, the vodka was flowing, they’re up 28-3.” Barkley was in a premature celebratory mood halfway into the game. Till his buddy, Tom Brady turned the tide.

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This was the first Super Bowl to go into overtime. Before, Barkley was confident the Patriots didn’t have the time to close the score gap. But the Falcons made a few mistakes and the ball landed in Brady’s hand.

It was over for Barkley then. The Patriots won their sixth Super Bowl title but Chuck lost.

Barkley still not over Super Bowl loss

The Falcons’ initial lead gave Barkley a false sense of security. He blurted, “Can’t wait for the end of the game to celebrate.” Barkley would get more drunk as he watched the Patriots turn the tide and $100,000 slipped from his fingers.

It must have also hurt to see the man that Shaq and Chuck called “pretty” cause Barkley to lose so much money. He tried to think of another one but nothing was as bad as this.

He previously said that was the first time he lost a bet on the Super Bowl in years. It wasn’t the last. History repeated itself in 2023 when the Philadelphia Eagles lost to Kansas City Chiefs.

Barkley lost $100,000 again and this time his ire was directed at Patrick Mahomes.

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