“Charles Barkley, You Saved Yourself $50,000!”: Competing for $20,000,000, Tom Brady Had a Hilarious Exchange With NBA Legend Despite ‘Woeful’ Loss at the Match

Charles Barkley has always had a thing or two for playing golf. He always loved playing that sport when he had a cordial relationship with Michael Jordan. Now that his career has transcended into becoming a sportscaster, he tried his hand at commentating in golf during 2020’s famous ‘The Match.’ The event was a celebrity golf game between two teams consisting of Tom Brady and Phil Mickelson versus Tiger Woods and Peyton Manning for a whopping cash prize of $20,000,000. Having significant gambling experience from his hay days, Chuck bet $50,000 on Tom Brady if he is able to hit the greens.

The cash prize of $20,000,000 was one of the highest of its time for a charity tournament back in 2020. With the COVID-19 pandemic at its peak, the winners of this tournament were supposed to donate this amount to help with relief efforts for COVID-19.

Tom Brady once saved Charles Barkley from a $50,000 setback in a golf bet

Throughout the course of the game, Tom Brady and Charles Barkley were in constant contact with each other. The veteran legends of their respective sports engaged in solid banter and conversations with each other, while Brady warmed himself up for the tee shot. As the New England Patriots legend was readying himself, Chuck offered Brady a bet to donate $50,000 in charity if he could keep the ball on the greens.

Here is the clip of the incident, posted by Bleacher Report on Facebook:

Brady was confident he could nail the shot. He even tried asking Barkley swing tips, which Chuck conveniently refused. Unfortunately, Brady’s shot hit outside the greens, which might have saved Chuck from a half-a-million-dollar setback. Reacting to his own shot, Brady told Barkley,

“Chuck [Charles Barkley], you saved yourself $50,000!” 

Fortunately, Tom Brady made it later in the game. The then-Tampa Bay Buccaneers quarterback holed a wedge shot, hitting a birdie on the seventh hole. But while doing so, his microphone slipped and his pants split, adding much to Charles Barkley’s humor.

After hitting the hole with that shot, Brady replied to Chuck and asked him to ‘shut his mouth.’ 

Tom Brady went on to win ‘The Match’ in 2022 teamed up with Aaron Rodgers

The 2020 iteration was won by golf legend Tiger Woods and Peyton Manning, who donated the prize money to charity. But Tom Brady wasn’t done yet right here. In the next iteration of this celebrity tournament in 2022, he went on to win alongside his partner and NFL colleague Aaron Rodgers. 

The duo participated against Kansas City Chiefs Patrick Mahomes and Josh Allen in the tournament. Rodgers’ clutch putt and Tom Brady’s consistency in golf helped the duo clinch the tournament title in this iteration. Besides that, there was plenty of banter among the players and the sportscasters, which fans watching definitely got to enjoy.