When it comes to gambling, Shaquille O’Neal and Charles Barkley couldn’t be more different. Shaq, always boasting about his calculated approach, seems to ride the wave of success effortlessly—claiming a profit nearly 25 times its original value this time around. Meanwhile, Barkley’s strategy is anything but cautious. “I love to gamble, I don’t like to gamble,” Chuck rarely left the table without at least a million dollars in hand. Yet, this time, fate wasn’t on his side. Barkley had to call it a night, hoping tomorrow would bring better luck.

Over on Inside the NBA, the antics about Barkley’s betting streak—or lack thereof—hit full swing. The NBA on TNT’s clip featuring the crew poking fun at his luck went viral. The caption hilariously read, “The Chuckster’s still looking for his first parlay win of the season 😆.”

Ernie Johnson opened the segment with a playful jab: “Come on, man. Is he still winless? Come on, Chuck. You still winless, Chuck?” The laughter that followed said it all, but Chuck’s reaction was the real kicker.

Then came the breakdown of Charles Barkley’s doomed parlay. His picks? Shai Gilgeous-Alexander (30+ points), Donovan Mitchell (20+ points), Jarrett Allen (15+ points), and Shai again (2+ three-pointers). Confident as ever, Chuck reasoned, “They got no other big guys. They should dominate.”

But when none of it panned out, Ernie couldn’t resist trolling him. “Do the folks at FanDuel ever call you and say, ‘Hey, Chuck, win one every now and then’?” Chuck, never one to back down, fired back with a sheepish, “Hey FanDuel, I’m sorry. I’m sorry. I’m not going to gamble anymore until tomorrow.” 

But why does Barkley gamble so relentlessly? On Club Shay Shay, he revealed his high-stakes rule: never leave the casino until he hit a million-dollar win. However, the losses stung. “I’d be depressed for a week [thinking], ‘Damn, I lost a million dollars?’”

Eventually, the risks outweighed the thrill, and Barkley took a two-year hiatus. “No matter how good it feels winning, when you lose, it just fu-king sucks,” he reflected. Though his break helped, the allure of those big bets remains strong. Meanwhile, his buddy Shaq keeps stacking wins.

Shaquille O’Neal made 25x profit with Parlay bet

Shaquille O’Neal recently found his groove in sports betting, placing a 6-pick parlay during the NFL Wildcard Round that paid off big time. Shaq nailed five out of six predictions, leaving the LA Rams’ game against the Minnesota Vikings as his only hurdle. Luckily for him, the Rams dominated with a 27-9 victory, turning his $500 wager into nearly 25 times its value.

Even before the final game, Adam Lefkoe had the inside scoop, teasing fans with an Instagram story about Shaq’s bet: “@Shaq is a Rams win away from turning $500 into $12k.”

Shaq’s predictions leading up to the Rams game were spot on. He called wins for the Texans, Ravens, Bills, Eagles, and Commanders with remarkable precision. By the time the Rams took the field, the spotlight was on his final pick—and it didn’t disappoint. The LA Rams sealed the deal, completing Shaq’s flawless parlay.

And Lefkoe couldn’t resist claiming some of the credit: “I had Shaq predict all of the NFL Wildcard games. I parlayed those picks. @shaq got them all right.” Considering Shaq’s earlier struggles with sports betting, this victory was sweeter than ever.

For those unfamiliar, parlay bets are no easy feat. They combine multiple wagers into one, and every single pick must be correct. Miss one, and it’s over. But Shaq? He got it all right, proving that even in betting, ‘Big Diesel’ knows how to win big.