Charles Oakley was well-known as one of the game's toughest players during his playing career. There is no doubt that many players loved to play alongside him, and Oakley is well-respected in NBA circles.
Eddy Curry has a friendship with Charles Oakley during his time on the Chicago Bulls. In an interview with Michael Scotto of HoopsHype, Curry revealed a crazy story about he and Oakley used to pretend to be policemen to avoid traffic, noting that he "used to be so scared", even thinking that he was going to be arrested.
I remember Oakley made me late for the plane. He’s my guy. After a home game, we’d be leaving and had a certain amount of time to get to the plane, but he had to go get his soul food. He’d always make me take him. I’d take him in his car. He could never get his food and leave. He knew the guy who owned it. He’d hang out like we had nowhere to be. They wouldn’t say anything to Oakley, but they’d say something to me for being late even though they know I’m with Oakley. He’d have me in his Range Rover on the highway. Every time we ran late, he had a switch that had police lights. He’d hit the lights and had me riding on the shoulder and barked out these orders while I was driving. I used to be so scared. I was like, “Oak, I’m going to get arrested.” He’s like, “F*ck that. You heard me. I got you. Don’t worry.” We’d barely make it to the plane.
There's no question that this is a crazy story to hear. Pretending to be cops is absolutely wild, especially doing so to avoid being late to get to a plane, rather than just leaving early.
There are definitely some other crazy stories about Charles Oakley, such as Kwame Brown's account of Oakley threatening to beat him up when Brown was a rookie. Perhaps we'll see more stories about him be told in the future, and it's clear that Charles Oakley had some interesting times in the league.