Rich Paul Reveals His Craziest Gambling Stories With NBA Players And Celebrities

Rich Paul has gambled with some very big names in the sports and entertainment industry.

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Credit: Fadeaway World

Rich Paul has been a gambler all his life and on The Old Man and the Three podcast, he shared some of his craziest gambling stories involving NBA players and celebrities. 

“Pistons are playing the Cavs in the playoffs,” Paul said. “In 06 or 07, fact check that. It was in the moment. We said we gonna go play cards. We end up having two card games in one area, and it’s the Pistons and the Cavs together. They have to play each other.”

The Detroit Pistons and Cleveland Cavaliers faced off in the playoffs in 2006 and 2007, so it is unclear which year it was. Paul realized at the table, though, the kind of opportunity he had.

“It’s Chauncey (Billups), it’s Rip (Hamilton), it’s Tayshaun (Prince) and I’m sitting here I’m saying to myself, ‘This was crazy, we are in the playoffs…’ But it’s Booray, it’s cards,” Paul continued. “And at the same time, I am saying to myself, ‘Rich lock-in. This is your playoffs. This is your Eastern Conference f***ing Finals… Don’t pull up for the 3 on a 1-on-none fast break because these guys got a lot, and are going to get a lot more. You, on the other hand, you need it.”

Paul said he did not blow it and when JJ Redick asked just how much he won, he stated it was a small property. The 41-year-old then revealed that the heaviest action he had was when he played Booray with Gilbert Arenas, Larry Hughes, Drew Gooden, and Dahntay Jones.

“We annying 2,000 a man playing Booray,” Paul added. “You know how crazy that is? And I’m not in the NBA. The minimum pot is 10,000, that’s the minimum.”

Redick explained how a $2,000 anny can turn into $126,000 very easily in five games. Paul joked that he had to be the craziest man in the world to get into this situation, as he was the only one there without an NBA contract. When asked who would win these games, Paul said Hughes won a fair few of them.

Having played against so many players in the NBA, it was inevitable that Paul would be asked to give his list of the best Booray players he had come across.

“He’s a coach now so I’m gonna use this against him, T-Lue,” Paul said. “(Russell Westbrook) is pretty good… (LeBron James) would be in there… Larry Hughes was a good player, D-Jones is probably one of the funniest guys to play with, and (Kendrick Perkins).”

Paul revealed he played spades with Michael Jordan when he was younger and also recounted an instance where he played cards with the likes of Jay-Z, Kevin Lyles, Will Smith, Tom Brady, and Alex Rodriguez in 2004.

“If they know you’re serious, you get a seat at the table, so they gave me a seat at the table,” Paul stated. “… That was kind of like my entry at that circle, I ended up winning that hand, won a little bit of money.”

Paul said he would be willing to gamble on any kind of game growing up. He has really honed his gambling skills and is certainly not one who you’d want to bet your life savings against.

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Gautam Varier is a staff writer and columnist for Fadeaway World from Mumbai, India. He graduated from Symbiosis International University with a Master of Business specializing in Sports Management in 2020. This educational achievement enables Gautam to apply sophisticated analytical techniques to his incisive coverage of basketball, blending business acumen with sports knowledge.Before joining Fadeaway World in 2022, Gautam honed his journalistic skills at Sportskeeda and SportsKPI, where he covered a range of sports topics with an emphasis on basketball. His passion for the sport was ignited after witnessing the high-octane offense of the Steve Nash-led Phoenix Suns. Among the Suns, Shawn Marion stood out to Gautam as an all-time underrated NBA player. Marion’s versatility as a defender and his rebounding prowess, despite being just 6’7”, impressed Gautam immensely. He admired Marion’s finishing ability at the rim and his shooting, despite an unconventional jump shot, believing that Marion’s skill set would have been even more appreciated in today’s NBA.This transformative experience not only deepened his love for basketball but also shaped his approach to sports writing, enabling him to connect with readers through vivid storytelling and insightful analysis.
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