“You might win but you ain’t gonna smack me without a fight” – Tyson Chandler on just how intimidating being a teammate of Charles Oakley was originally appeared on Basketball Network.
Playing alongside enforcers, those versatile, physically imposing players, comes with its own set of challenges. They will go to war for their teammates, never allowing opponents to bully anyone on the court. But sometimes, their fire doesn’t stop with the opposition. They expect total respect, and if it doesn’t come willingly, they won’t hesitate to get feisty, even with their own teammates.
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For rookie Tyson Chandler, that reality hit him hard when he shared the court with a 38-year-old Charles Oakley during their time together on the Chicago Bulls.
Chandler loves Oakley, but knew he was crazy
Oak, who made his debut in the NBA in 1985, was molded by an era when physicality ruled the NBA. Fights, hard fouls, and intimidation weren’t just tolerated, they were the norm. Oakley quickly built a reputation for being one of the league’s toughest enforcers, particularly during the early days as Michael Jordan’s unofficial bodyguard on the court and later as a defensive anchor alongside Patrick Ewing in New York.
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So naturally, when Oakley took it upon himself to pass his wisdom to the next generation, it was never a soft-spoken relationship. It was more like a boot camp. And if a rookie like Chandler dared to speak out of turn or talk back, Oakley wasn’t the type to let it slide. He made sure that lessons were learned, most often in the hardest way.
While appearing on the ‘All The Smoke’ podcast, Chandler recalled a wild encounter with Oakley, where what started as a minor disagreement turned into a full-swing wrestling match. Perhaps a genuine ‘welcome to the league’ moment, in trademark Oakley style
“Oak, made me roll. I love Oak, man. He was the best vet. But he would rough me up, too. I remember we were in film and I’m sitting in front, he would always talk to me and Eddie. He said something in the film, like, ‘imma smack you too.’ I said, ‘You might win, but ain’t gonna smack me without a fight.’ As soon as I said that, Cart (Bill Cartwright was like, ‘Film’s Over!’ Then we get to the stairs, and then we start tussling. He was strong as s–t. I come back into the training room, back cut up. Trainer’s like, ‘What happened?’ I was like, ‘Me and Oak was wrestling,’” Chandler said with a smirk on his face. “Oak was crazy as hell.”
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Charles Oakley was one of the fiercest enforcers in NBA history
In today’s NBA landscape, where situations like Draymond Green punching Jordan Poole are met with immediate media backlash and public scrutiny, one can only imagine how the Oakley-Chandler incident would have played out in the court of public opinion. It would’ve sparked debates and indeed, there would’ve been no shortage of controversy. Yet, even with that kind of intensity, Oakley was deeply respected by his teammates.
It is safe to say that Chandler’s admission makes it understandable that those who played with Oakley still respect and admire the lessons. For the latter, traits like respect and toughness went hand in hand.
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This story was originally reported by Basketball Network on Jul 20, 2025, where it first appeared.