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.'”