For instance, on the golf course, The Chuckster not only bet against Tiger Woods but also engaged in heated trash-talking. However, the outcome only saw the premature boasting of the 6’6” forward getting turned into humiliation.
Barkley trash-talked Tiger
As Chuck’s prominence grew, he devoted considerable time to golf. His friendship with former NFL receiver Roy Green and golf legend Tiger Woods bolstered his confidence in his golfing abilities to such an extent that he believed he could outperform any opponent.
Green recounted an incident where Sir Charles’ self-assurance reached such a point that he challenged the PGA Tour legend for a wager, the stakes of which could have ranged from a modest $5 to an extravagant $500,000.
“We get there, and Charles goes, ‘I think I’m gonna whoop some a** this time.’ I said, ‘Look, man, I just want to know the bet, Chucky, ’cause I’m betting for Tiger.’ Charles says, ‘OK, I’m gonna take Tiger five a side, but Tiger’s gotta give me one a hole and two on par 5s,'” Green said. “I’m like, ‘S**t yeah, I’ll take it, too.”
Moreover, after Woods mishit his initial shot, the 11-time All-Star’s confidence in his impending victory swelled to such a degree that he referred to the Hall of Famer as ‘a f***ing overrated guy.’ However, upon reaching the second hole, Tiger began to exhibit the superstar-caliber play for which he was renowned, and the outcome only left the Chukster in the position of having to fulfill the financial obligation.
“After that hole, Tiger birdied five straight,” Green recalled. “I said, ‘Chucky, you can buy out right now, or we can play the back too.’ He said, ‘I’ll buy out the bet.'”
Was Barkley too optimistic about his golfing talent?
While one might assume that challenging the golfing GOAT would require considerable confidence, but Barkley was not quite at that level. This was evident when the 1993 MVP, before the final day of the 2021 American Century Celebrity Golf Championship, bet $100,000 on himself to finish within the Top 70 in a field of over 80 participants. To his surprise, he only finished in the joint at the 76th position.
"Well, I put $100,000 on myself [to finish top 70], so I feel very confident.” – Charles Barkley
Chuck finished T-76… pic.twitter.com/XMULpQ2MDC
— Tim Reilly (@LifeOfTimReilly) July 11, 2021
This, for someone who struggled to rise from the lower ranks in a competition, challenging Woods was perhaps too optimistic, to say the least.
