It was not Allen Iverson or Shaquille O’Neal who made Michael Jordan stutter. Someone who made the Black Cat fight for it was streetball legend Kenny Rogers. No, it’s not an NBA player sharing the same name as the music legend. Country music icon Kenny Rogers stumped the young and gangly Michael Jordan once. But MJ had to get back at him (surprise, surprise). All for a good cause, though.

The songwriting royalty used to attract sports’ biggest names to his 1,200-acre Beaver Dam Farm in Athens, Georgia, for a three-day fundraising extravaganza for the Kenny Rogers Classic. It was so big that it aired on NBC. NBA titans like Larry Bird, Isiah Thomas, Dominique Wilkins and Michael Jordan took on Rogers and his ragtag group of basketball amateurs in the 1988 televised charity event. And if history is evidence, MJ didn’t hold back.

The one year The Gambler chose to play 3vs 3 basketball, Thomas led Team Blue, Bird led Team Green and Jordan led Team Red (no surprise there). Rogers was on the White squad with Wilkins. That year, 25-year-old pre-championship scrawny Jordan, the reigning Defensive Player of the Year, was outmatched by the guitar-strumming Grammy legend.

Rogers did a textbook pump-fake, yelled, “A fake!” sending Jordan flying past him. Legendary broadcaster Chick Hearn described it as, “Kenny Rogers puts Jordan in the popcorn machine.” All while the singer stepped to the side and calmly drained a 21-footer. Let’s just say ’80s NBA stars are lucky Rogers chose to take up music.

Rogers is lucky, too, that this was a one-night charity event. While NBA players were walking on eggshells to not trigger Michael Jordan, the singer made a mistake of embarrassing him.

Michael Jordan gave Kenny Rogers the DPOY treatment

The day Kenny Rogers pump-faked on Jordan went down in history for all the right reasons. His Airness switched on ‘Revenge Mode’ and promptly corrected the slight. A consequence even Larry Bird had to pay for.

During a season when cynics thought that the one DPOY credit was a fluke, he put on a defensive masterclass for a mixed bag of NBA players and celebrity basketball enthusiasts. He swatted balls away with a specific focus on Rogers. The singer demonstrated his awesome skills with a great wraparound pass but Jordan even blocked that one slight.

On his second of ten scoring title runs in the NBA, he played this charity game like it was a real game between the Bulls and Celtics. In that little half-court arena in Rogers’ home, Jordan sent the ball flying into the ceiling most times.

Top Stories

South Florida Medical Professional Arrested After Incident at Unrivaled Basketball Event

Is Kevin Durant Dating EJ Johnson? Fact Checking Viral Claim

Giannis Antetokounmpo Turns Villain for Milwaukee After Unexpected Gesture to Crowd

LeBron James Washes His Hands of Rich Paul’s Actions in Damage Control Attempt

“Dirty Player”: Calls Mount on Shai Gilgeous-Alexander After Alleged Attempt to Hurt Victor Wembanyama

Wilkins was collateralized by being on Rogers’ team. Jordan caught Nique mid-dribble and did a circus layup right before a clutch shot that tied them at 20.

The revenge was complete when Rogers was guarding MJ on the final play. The Bulls icon did his usual clinic, snatched the ball, drove deep, spun midair, and banked that shot with his back to the basket. Team Red won 22-20, easy-peasy.

Larry Bird didn’t make any such mistake in their matchup. That’s probably why MJ held back and let Bird’s Green Team win with a considerable lead. But not before hitting him with a few reverse layups and circus shots.

Before Rogers passed away in 2020, his annual charity event was a beloved spectacle as big as the All-Star Weekend. The Kenny Rogers Classic was always about bringing celebrities together for a good cause. But the ’88 game went down in history for proving that even for charity, the Jumpman brings his competitive flair.