The “Oak” was, quite frankly, THE scariest son of a bitch. That can’t be understated. The mammoth enforcer of the New York Knicks was essentially the godfather of the flagrant foul, and if there was a skirmish or bodies hitting the floor, it was certain that Oakley would be in the middle of it. Plus, he always had this crazy look in his eye that convinced me that he was somehow related to Chuck Manson.

Oakley is one of those guys who should be the subject of those Chuck Norris-type statements that attest to how grand someone is. Like, “when prison commits a felony, it goes to Charles Oakley to serve its time.” Or, “Lebron James can dunk from the free throw line – Charles Oakley can dunk Lebron James.” Or maybe, “Kids like dressing up as Dracula for Halloween – Dracula dresses up as Charles Oakley.” He’s that type of legend.

Some fun Oakley stories:

– Oakley had a feud with opposing forward Tyrone Hill that stemmed from a dice game. Apparently, Hill owed Oakley $54,000, but didn’t pay up. As a result, Oakley doubled the amount owed and then began assaulting Hill. First, he slapped Hill in the face during a pre-season game. Later, during a morning shootaround, Oak slammed a ball into Hill’s unsuspecting head. Needless to say, Hill eventually paid the man.

– Oakley once slapped Charles Barkley at a Player’s Union meeting. Apparently, Barkley had said some things about Oak that Oak didn’t care for, thus the slapping occurred. Not only did he tell Barkley that he was going to slap him every time he saw him thereafter, but he also had the hilarious line of “… you need to change your name – I’m the only ‘Charles.’”


– Jeff McInnis incurred the wrath of Oak when, at some point, Oak discovered they were both dating the same woman. The next time Oak and McInnis were playing against each other, Oak walked up to McInnis before the game and punched him in the head. McInnis responded by going after Oak with a plastic cup holder, which resulted in Oak laughing.

– Got into an on-court wrestling match with Shaq after a series of hard fouls (delivered by Oak of course).

– Apparently mentored Ben Wallace. You know, the guy who was essentially the initial catalyst of that Pistons/Pacers brawl you may have heard about.

– Check out this story from the, sent in by a reader, regarding an encounter he had with Oakley when the reader was 13 years old:

… I was walking past the hotel’s tiny-ass gym, and noticed it was empty except for Charles Oakley, who was working out on a stationary bike. Oak looked like his usual menacing self, but being from New York those mid-90s Knicks teams were my favorite growing up, and I had to get his autograph.

So I went up to him and I was like, “You’re Charles Oakley, right?” And he gave me a grunt that I’m pretty sure in Oak-speak meant “Yes.” Encouraged, I said, “Wow, I’m a big Knicks fan, I love the Knicks! Can I get an autograph?” 

All he said was “Nah.” Then he looked away, and just kept pedaling. I sulked out of the gym, ashamed.

– Oak was roughed up by security guards in Vegas over Lord knows what (resulting in a broken arm, among other things). The most noteworthy part of this (besides the fact that somebody got the better of Oak – probably took 4 dudes) is that it occured about 4 months ago.

So, it continues. Michael Jordan hangs out with Oak TO THIS DAY, just for security purposes. That says enough, but my favorite Oak line had to be in response to one of his many fights (this particular one was with P.J. Brown):

“Didn’t nobody bleed.”

Brilliance. It’s a great line for life, in general. Next time you blow it at your job, just let ‘em know… didn’t nobody bleed. Lay down with your girl’s best-friend? Didn’t nobody bleed. Try it out sometime although, chances are, it won’t get you as far as this guy:


Wes Lilliman can be contacted at


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