When Charles Barkley bet Michael Jordan $500 saying he didn't weigh more than 290 lbs: "Hell, yeah, I'll bet you”

Michael Jordan and Charles Barkley were considered best friends before the two NBA legends' relationship turned sour. With the competitive nature of the former Chicago Bulls' star, Jordan was known to pick on Barkley about his weight and even made a wager.

This happened when a 39-year-old Jordan was still uncertain of his future in the league and if he would still play in the 2003-04 season. The six-time NBA champion went to Barkley and invited him to make a comeback in and play with him in the NBA.

At this point, Barkley was retired and had played his last NBA game almost three years back with the Houston Rockets. In his last NBA season, he averaged 14.5 points and 10.5 rebounds a game.

Barkley was happy that Jordan considered returning to basketball with him under the conditions that he got in shape.

In a story shared on SI.com, the two NBA stars made a phone call to update each other's condition.

"Hell, yeah, I'm good," Barkley told Jordan. "I'm working out, not drinking, getting my fat a** in shape. I'm too good-looking to be fat."

Michael Jordan was willing to bet $500 that Charles Barkley was 290 pounds or over.

"Hell, yeah, I'll bet you. We'll go five hundred," Barkley said. "Yeah, I'll do it. No, not on TV. I'll do it after I work out today. I'll check in with yo' a** later. All right, boy, be safe."

Michael Jordan and Charles Barkley's planned return failed

As the two former Dream Team teammates discussed returning to the NBA at 39 years old, the plan came down the drain after Jordan had to have a knee operation in February 2022. This forced the five-time NBA MVP to call it a career after the 2002-03 season.

"All those plans got smacked in the head when Michael went under the knife," Barkley said. "If Michael can't make it back, no one can."

During their prime, Jordan and Barkley faced each other in the 1993 NBA Finals. The Chicago Bulls won in six games over the Phoenix Suns en route to Jordan's third NBA championship. This was the first and last time when Barkley appeared on the NBA's biggest stage.

Michael Jordan averaged 41 points, 8.5 rebounds, 6.3 assists and 1.7 assists during the series. Meanwhile, Charles Barkley held his own, averaging 27.3 points, 13 rebounds, 5.5 assists and 1.2 blocks in six games.