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Despite Getting Stripped of $20 Million for Michael Jordan-Like Addiction, Charles Barkley’s Gambling Stint Disclosed by French HoF

Published 09/25/2023, 9:10 AM EDT

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Even though sports itself is thoroughly entertaining, it does need some extra enhancement. While there are many forms of that, media analysis and television remain the most common and useful. But, even among the coverage and commentary are tiers of brilliance. However, one that is consistently at the top of the entertainment food chain is Inside The NBA. Featuring Charles Barkley, Ernie Johnson, Kenny “The Jet” Smith, and Shaquille O’Neal, the show is a constant highlight. Among the many bits on the show, one borrows from Chuck’s love for gambling.

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A trait he might have taken from friend-turned-enemy Michael Jordan, Barkley’s gambling prowess is universal. As a result, it even led a 4-time Champion to revel in its memorability.

Charles Barkley steals the show at the Hall of Fame


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Despite the magical night honoring the league’s greats, it was Barkley that left Tony Parker with a unique memory. One that he still considers among his best. On his brand new SKWEEK SHOW, the San Antonio Spurs legend went in depth about his two favorite memories of the event.

Last year when I went for Timmy [Tim Duncan] and Manu [Ginobili]. It was meeting all the legends.” However, the Chuckster left a unique impression.


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I was able to gamble with Charles Barkley. So, that was pretty cool. I always heard stories about Charles Barkley gambling. It  was my first time gambling with him two years ago at the Hall of Fame.” 

Of course, it is the Chuckster‘s propensity for gambling that gave birth to one of the best gags in all of sports television. Barkley raising his voice and shouting “Guarantee” is a constant highlight for most NBA matches, especially due to the fact that his guarantees almost always tend to be wrong.

But, this habit that the Philadelphia 76ers legend got from friend Michael has been costly as well.


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Barkley’s expensive guilty pleasure

Even though he got the habit from Michael Jordan, the dividends haven’t been the same for the two legends.

Unfortunately for Barkley, the entire endeavor has cost him a ton of money. This year alone, he lost $100,000 on the Super Bowl after betting against Patrick Mahomes and the Kansas City Chiefs. Overall, the former MVP claims to have lost nearly $20,000,000 in his gambling tenure.


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According to the Round Mound of Rebound, the lure of small victories inevitably forces large bets out of him, compiling up the losses. While his luck seems to not favor him as much, it would interesting to see how his time with Tony Parker went about.

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Priyanshu Choudhary is an NBA Writer at Essentially Sports. Basketball has been his favorite sport for over a decade, and he has written close to 300 articles. If asked what he loves about the sport, Priyanshu would cite the technique, the breakdown, the ebb and flow and the theatrics that have endeared him since 2009.
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Edited by:

Aakash Nair