In a month, Shaquille O’Neal added a third Tesla Cybertruck, a Mercedes Sprinter van, and his car dealer’s own S550 to his massive car collection. Charles Barkley, though, is not an autophile and impulse buyer like his big bestie. But he is an impulsive gambler, for sure. “There have probably been seven times when I won a million dollars. But there have probably been 25 times when I’ve lost a million,” Barkley had famously (or, should we say infamously?) said about his gambling obsession. Despite that, it seems that he is in for that. He’d rather gamble away his TNT paycheck than splurge on shiny wheels.

Barkley made that very clear on his return to The Dan Patrick Show. Though he fished for a free car from the show’s sponsors, Barkley rejected the idea of having luxurious, exotic cars. “I got money for a reason. I’m not stupid. You can’t have money if you waste money on stupid stuff.”

Chuckster confirmed his primary car is a Kia, and he also has a Ford Expedition. But no custom Rolls Royce, Teslas, and Mercedes like a certain someone. When Dan Patrick did point out, “Doesn’t Shaq have a bunch of fancy cars,” Barkley also had to remind him that O’Neal’s net worth is $500 million.

Sir Charles didn’t earn a fat paycheck the way Shaq did during their overlapping NBA careers. They do have similar contracts at TNT, earning roughly $10 million a year. But Shaquille O’Neal is an endorsement machine with a gazillion investments. Barkley has at least Nike stock, is an investor in Redmont Vodka, and is now a producer through Round Mound Media. It’s boosted his net worth to $80 million, smaller compared to Shaq but not trivial by any means.

Patrick suggests that Chuck would have a lot more money if he didn’t gamble. After all, he had a dazzling NBA career. The 2006 Hall of Fame inductee averaged 22.1 points and nearly 12 rebounds in a 16-year career that included stops in Philadelphia, Phoenix, and Houston. He was the league’s MVP in 1993, and he won gold at the ’92 Barcelona Olympics as part of the original U.S. Dream Team. However, the NBA legend countered, “There’s no chance of that happening. Dude, I like to gamble. What’s wrong with it?”

But surely, certain things are not so right. What’s not great about Chuck’s habit is that he doesn’t win a lot, like most of the gamblers. For a long time, he’s wagered on the Philadelphia Eagles for the Super Bowl title. The Patriots or the Chiefs make him lose $100,000 each year. He’s also infamously lost too much money playing against his former best friend, Michael Jordan. Can you imagine exactly how far did he go with his gambling habit?

Barkley had revealed on the ‘Club Shay Shay’ podcast that he could have had multiple winning days of $600,000 to $700,000, but he would carry on until he could take home a million.

“We’d be sitting there, I’d get up and my friends would say, ‘Chuck, we’re going to spend the night.’ And my head would say, ‘No, we’re not leaving this son of a bitch until I win a million dollars,” he had said. On multiple occasions, this tendency has led him to ultimately lose a million. Interestingly, though Charles called Shaq’s car spree stupid, he had the same to say about his gambling as well.

“Do I have a gambling problem? Yeah, I do have a gambling problem but I don’t consider it a problem because I can afford to gamble. It’s just a stupid habit that I’ve got to get under control, because it’s just not a good thing to be broke after all of these years,” Barkley had said in 2006 in an interview with ESPN. But at the same time, he was bold enough.

“I’m going to continue gambling. I like to gamble. It’s really nobody’s business because it’s my own money, I earned it,” Barkley had said on that occasion. However, despite his love for gambling, Barkley had expressed his concerns about the proliferation of sports betting.

“There’s too much of it. We’ve got people in the stands betting on who’s going make the next free throws. Think about that. If I was a scumbag, I’d look at a guy in the stands, a friend, and say, ‘Yo, I’m going to miss both of these free throws.’ Now, that’s cheating,” Barkley had said in 2022 during a media event ahead of the annual American Century celebrity golf tournament.

As the market has grown, sports betting advertising has also seen an upward trajectory. Sportsbook brands in the U.S. spent an estimated $282 million on national TV ads from September 2021 through May 2022, a 281% year-over-year increase, as reported by iSpotTV, a firm that measures the impact of TV and streaming advertising.

“I had an NBA owner say in the next three to five years … they’re going to be making triple what they do on television revenue, And when you get to that point, I think it’s really scary. I mean, c’mon man, if you’re able to bet on if a guy’s going to make two free throws in the middle of a basketball game, that’s obsessive,” Barkley had said while also adding that there was no turning back from that point. Maybe just like his own self! With that, Barkley has even lost a few fake bets to Shaq too. But, it doesn’t look like O’Neal ever made Chuckster pay up. If you ask Barkley, Big Diesel doesn’t need any of his money.

Charles Barkley is right about Shaq

Charles Barkley has long maintained that Shaq has way too much money. He said the same to David Letterman after the big man bought a hookah bar on a whim. It’s interesting that Barkley asked Patrick for a Mercedes now because O’Neal just got two. If Barkley’s obsession with gambling is one for the storybooks, Shaq’s car addiction is no less than a legend. Let’s take a look at an incident.

In 2022, Shaq revealed on the podcast Drink Champs his interaction with a luxury car salesperson that resulted in him Shelling out a hefty amount. He said, “I don’t wanna spend $400,000 for a car. So I’m like, ‘Hey man how much is this? Nah. How much is this one?’ So finally the old guy says, ‘Yo man, you asked about all these cars, can you afford them?'” The naive question did not sit well with Diesel. So what did he do?

“Now I’m pissed. I said, ‘What the (expletive) you just said to me?’ So I buy three. That one, that one, and that one, and I want them dropped off. Move the seat back. So I got 3 Rolls-Royces that I never drive. So there goes another million,” Shaq had said! In fact, he has also gifted a Rolls-Royce to LeBron James on the latter’s 25th birthday. There are even crazier instances of his car-love.

His friends at Effortless Motors delivered a brand new customized Sprinter van to Shaq’s Atlanta mansion. The owners drove over in their personal Mercedes S550 which caught Shaq’s eye. The giant bought his friend’s car right there in his driveway and the former owner had to leave in an Uber. This same guy recently said he’s got 40 cars and doesn’t need any more!

Previously, Effortless Motors delivered a black-on-black customized Cyberbeast to Shaq’s Atlanta mansion. Shaq already had one in Las Vegas and wanted a second one in Atlanta, too. The same dealership just gifted Shaq his third Cyberbeast with a customized wide-body kit. Shaq could roll up to Studio J in his new Sprinter or Cyberbeasts on Tuesdays at Thursdays. But we’re betting Chuck’s not jealous at all.