Charles Barkley Hilariously Stripped Ex-ESPN Employee Only to Find Face Stamped on Butt

Charles Barkley’s (fake) beef with Dan LeBatard, his dad, and his entire crew goes deep. The peak of this beef had to do with the 2011 NBA Finals. If you were among the lucky ones to escape the visuals because of Miami’s Big 3 losing this one, Chuckster and Dan had the most questionable bet over the Finals. It might be typical Chuck Guarantee madness now, but back then, his prediction was pretty bold. So LeBatard was overconfident in his stance. Over a decade later, he and his crew look back on the best moments of The Dan LeBatard Show and why this bet was iconic in sportscasting history.

This was when the Dallas Mavericks led by Dirk Nowitzki and JJ Barea were taking on the Miami Heat Super Team in the 2011 Finals. Everyone was sure LeBron James and Dwyane Wade would win their first chip as teammates. One renegade stood out from the crowd. Charles Barkley bet his money, pride, and dignity on the Mavs. His prediction raised as much eyebrows as he and LeBatard wagering the loser does the equivalent of Cersei’s walk.

As history went down, Barea locked Bron in the post, which Dan never thought could happen, and the title went to Dallas. So Miami native Dan threw a party to go through his bet in style. Sir Charles was there to ceremonially take off the robe. The wager was that the loser struts his stuff in a speedo. Dan went a step ahead with body paint and placed Chuck’s face in a choice position of his speedo.

The crew relived this crazy moment in sports in 2024 and they still melt in secondhand embarrassment. Even 13 years later, LeBatard says, “I was really confident that LeBron would dominate JJ Barea in the post. I feel like I had a position of strength. I didn’t think there was any circumstance under which the bet would end that way. I thought for sure the way that would end with Charles Barkley never calling us back because he’d lost the bet and he wasn’t going to do this.”

What’s even remarkable is that Stugotz still calls it a “bold” prediction by Chuckster like the Miami Big 3 losing never sunk in. Somehow, Barkley never specifically comments on his face on the electrode’s derriere.

Chuck was recently on LeBatard’s show but they didn’t relive their bet again. Maybe because most of the crew wants to erase that visual from their minds.

Sir Charles took the visual tribute with humor

An interesting tidbit that came out 13 years later is that Charles Barkley almost missed the spectacle his wild prediction caused. Both the show and Chuck had to carve out time for the day the TNT analyst was in town in 2012 when the Miami Heat was on its next deep playoff run. They made a wager then too and LeBatard won this one with the Miami Heat clinching the title.

Though he spent the whole year preparing for this bet, LeBatard now admits that’s the most scared he’s ever been in his career. But he’s glad that people got some entertainment over it and it became an iconic moment in an already iconic NBA Finals. Like, it gave birth to a ‘Speedo Man’ theme song to the timeless Batman theme.

Barkley never outrightly commented on the bit but by all accounts, he enjoyed the entertainment. The show’s crew said he was laughing the entire time, especially when Dan interviewed him in that appearance.

Chuck has a history of betting against the Heat, including on Inside the NBA. He still hasn’t paid up the $1 billion to Shaq. LeBatard is confident Chuckster would never have followed through with the bet if the Mavs lost. But they tiptoe around that question to stay in Chuck’s good graces.