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Charles Oakley is truly a bad man. And this is the best compliment you could possibly give him. In his NBA career with Michael Jordan’s Bulls, Pat Riley’s Knicks and Vince Carter’s Raptors, Oakley was both a terror on the boards and the ultimate protector of his teammates, and now he’s published a memoir, The Last Enforcer, whose title speaks for itself.
Oakley’s willingness to stand up for himself and his team – he says he’s nowhere near a bully, but won’t be pushed around – made him one of the biggest fan favorites of the nineties era of hoops. There was Oakley on Michael Jordan’s Bulls teams, duking it out without anyone who misstepped on a nightly basis. When he got traded to the Knicks, his star exploded in New York as the face of a famously physical roster built by Pat Riley. The Knicks never won a championship, but no one forgot Oakley as he played his last days above the border in Canada, still pushing and shoving players like a big kid on a playground.
In more recent years, Oakley has been in the news for his ongoing dispute with Knicks owner James Dolan, who once forcibly kicked him out of Madison Square Garden, leading Oakley to file a civil lawsuit. Now he wants a new generation of NBA fans to know his story, and so Oakley sat down with GQ to discuss his career highlights, his new memoir, his lifelong beef with Charles Barkley, how he once tried to beat up Judge Greg Mathis over a $1,500 bar tab, and who his favorite big men in the NBA are right now.
GQ: In the '80s and '90s, there were plenty of tough guys in the NBA. What made you never want to back down to anybody?
It was in my heart. You know, my grandfather [used to say] just stay on your craft. Just believe in what you believe in. Don't give in. Don't be weak…You had to be tough growing up in Cleveland. You don't know what is going to happen. Playing football made me tougher too.
You wrote in The Last Enforcer that you will be like this until the day you die. Should we expect some post-60-year-old Charles Oakley dust-up stories to happen or are you going to keep it chill?
Stories are stories. I mean they say if you can live to be 80, you should be able to talk, read and do stuff. So my thing is: It ain't like I'm out hunting for stories. Just life, you know, stuff happens around you. In this book, I had a lot of situations, I had to be tough. I couldn't let nobody just come and run over me. You know, with the Judge Mathis situation, he tried to run on with me, but instead, he got checked.
Would you mind telling me the story of how you tried to whip Judge Greg Mathis’ ass?
It's a long story.
I’ve got time.
Well, okay. It started in Cleveland.
As most bad things do.
I usually have a [party], every Labor Day weekend, for seven years in a row, right? People come in from Chicago, Detroit, New York. So we have an activity weekend. And I had a club [I liked] called Togo. So, basically we would meet at Togo for happy hour, and then we would go downtown to the Mirage. But [in 2004] because flights were delayed, this and that, I picked a couple people up and we went down to the Mirage. So I'm just relaxing, having a good time. This guy comes over and says, "I need to talk to you tonight."
Everybody wants to talk to you when you come home. So I'm talking with this guy, right? Another guy walked up and said, "Oh I need to talk to you." I said, "Give me five minutes." So a couple minutes go past. Here he come again. He said, "Oh, I..." I said, "I told you. Give me three to five minutes." So next time he walked up to me, he touched me and I hit him.
To be clear, this isn’t Judge Mathis, right? Before you even get to the story of that fight, you got into a separate fight on the same day?
I said, "Man, I told you to give me three to five minutes." [After that], I said, "Let's get out of here." So I leave [to go see] the O’Jays. We drive to Detroit. The show has started. They left tickets. We go backstage. We only hear like four or five songs. After the show, [former NBA player] Derrick Coleman was there. He had a restaurant in downtown Detroit called “Sweet Georgia Brown.” I walk in, there’s Judge Mathis, Queen Latifah, Tavis Smiley…Kwame Kilpatrick, Eddie Levert from the O'Jays. So we’re just standing there talking, having a good time. About 45 minutes go past. Here comes Judge Mathis.
He says, “Here go, your check. Your people drinking like it ain't no more water in this place.”
Oh shit.
I was like, "Who you talking to?” He says, “You.” I was like, "Man, get out of my face!” Derrick says, “Oak, just chill.” No! You tell him to chill. It was getting out of hand. [In the book, Oakley writes that a Mathis comment about his girlfriend leaving him for Queen Latifah, who was also at the bar, "took [him] over the edge," leading him to push Mathis "real hard."] Eddie Levert tried to calm me down, “Oak, Oak.” No, [Judge Mathis] was being disrespectful. I told Eddie, He ain’t no f’n good! He gon’ bring me the check. It wasn’t about how much it costs.
It’s the principle.
Yes. It was about how he did it. He said “I’mma make these NBA boys pay for it.” He was out of order. He's gonna tell me, “I’m gonna call my boys [on you].” He said, “This my city!” I don’t care whose city it is. You don’t tell anybody that you got some boys to come get me. He was dead wrong. It got kinda crazy.
Have you seen him since then?
I’ve seen him at Jordan parties, I saw him at a hotel at 59th and Central Park at the Ritz Carlton. I see him get out the car, but he don’t see me. I get in the elevator and hide in the corner. So when he come in there and pushed the button, he looked like he was ‘bout to pass out. I just looked at him the whole time, didn’t say nothing. He wanted to back out of the elevator. I wouldn’t have let him off. You gon’ ride up with me, buddy.
So, y’all do still have beef?
No, I don’t have no beef. I just had to let him know! He was dead wrong. Everybody says he’s so arrogant. But you don’t tell nobody that you gonna call somebody on them. Not where I’m from. I shoulda did him like a deer down South: tied him up and put him on top of my truck.
For someone who’s become famous as an enforcer, do you think there’s an art to fighting?
I don’t know. I don’t think about it. If I fight, I fight. I don’t go around picking on no one. I’m trying to be that officer off duty, you see something wrong, you go help someone.
What was the impetus for writing a book? Why now?
Playing in New York, being in the back page of the paper, playing in the league for so long as a tough guy, as an enforcer, I wanted people to really feel that real me with the stories I went through. I had to be tough, and tough-minded. When people see a weakness, they’ll try you. And they tried me. Any time I went out in New York, bodyguards and security always wanted to try me for some reason. I had so many run-ins, I try not to go out.
You have to protect your family, I’m always that big brother. If you’re with me, you got a chance.
I believe that. New York and the Knicks are a massive part of this book. You mention that, even before the incident at Madison Square Garden in 2017, you and James Dolan had another altercation in New Orleans. What happened?
[Dolan] and World Wide Wes (William Wesley, now a senior basketball advisor for the Knicks) were together. I was with LeBron and them. Someone came out to get me, to go back and meet [Dolan.] The man said, “this is Mr. Oakley,” and [Dolan] never turned around and shook my hand. I was like, “wow.” I walked back out and told LeBron and them what happened. It was so rude for him not to acknowledge me.
You go from that to 2017 and the civil suit. What actually happened that night?
We still trying to fish that out the water. That’s a fish that don’t know any water. I came down the steps to take my seat. Ten minutes later, here come eight guys. [James Dolan] just don’t want me there. He don’t wanna dance to my music. I might’ve said something in the paper about the team. Somebody ask me a question, I just answer it…it’s my opinion. I know talent more than you know it! But he’s a control guy.
You’ve labeled this man as someone who “bullies people because he has money and power.” Do you ever want to mend your relationship with the Knicks? Don’t you want them to retire your jersey?
We had a meeting, actually. And he brought that up. That’s like guilt to me. You never talked to me about my jersey until this happened. Hell, you ain’t even retired Bernard King’s jersey, how you gonna retire mine? And he’s in the Hall of Fame. [Dolan] just wants a big splash like we’re the best of friends.
Do you think the NBA has gone the opposite direction to when you played? Do you think it’s “softer,” as you write in the book, or is the game different?
It’s just different. It’s a different space. It’s a different time. It’s a young generation. It's more of a sexy game now. Everybody wants to shoot threes, high pick and roll. So that's where the money is. Global money.
Who’s your favorite big man in the league?
I mean, you gotta go with Embiid and Jokic in Denver. They’re the best big guys in the league. It’s a different league. You see these guys handle the ball and bring it up the court. Jokic’s getting 30 points and eight assists, 15 rebounds on a regular basis. And Embiid is just killing them! He's just like Wilt Chamberlain was back in the '60s. He's just bigger than everybody.
When Scottie Pippen first got to the Bulls, there was a famous video of you slapping Scottie when he was a rookie.
The vets control the locker room, they make the young guys go get donuts, newspapers, coffee sometimes. I did it once, and after that, I tied his shoes up tight and told him, “Next time somebody asks me to do this, they got a fight on they hands.” When Scottie and Horace [Grant] came in, they were real simple. They were called Salt and Pepper, like the rap group. One had a black car, one had a white car. They did everything together, like two shoes tied on the same side. They were fun, Scottie was real cocky. He said back then, “I want to be better than Mike.” I guess he still means it because he still says it. He’s living with that.
There was that famous lip sync video too. How’d that happen?
[Laughs.] We were in Phoenix. We got outta a shootaround and most times we got back to the rooms and played Tonk or Spades. And I said, "Man, MJ, let's go to the mall. I'm going to tell Mike Brown to get Scottie and Horace and bring them to the mall." We were walking past, and we go in there and make a video. Everybody was down for it. We had a good time. I mean, that was trying to bring the guys together. We did a lot of stuff like that.
Like, me and Mike Brown would take on the whole team. On the road, MJ would always get a suite. We would get some wings and play cards or something. As we clear the room out at night time, if me and Mike Brown leave together, the others wouldn’t come down. They tried to stick together. Because we used to catch one of them in the hallway, and just beat them up and stuff like that, but not too hard though [laughs]. Most times, we’d check out of the hotel and the room was trashed. So, we'd get MJ to sign a ball and leave the hotel.
Wait. For fun, on the road for professional basketball games, you would sneak up on ya teammates and just beat their asses?
Yep, on the elevator, everything. We catch them by themselves, and then you can forget it. They always try to sneak out by themselves. We catch them, oh, man [laughs]. It was fun, though [laughs]. Nobody really got hurt or nothing, nobody. It was just fun.
How much were you betting on Tonk?
Twenty on the game, 20 on spades, so you can't get hurt too bad. It's just a good, friendly game.
$20?
Twenty….dollars. You can lose $20 a hand. But some teams play if you go down and get caught, you got to pay for everybody on the team. I don't like that way.
Obviously, you got traded from the Bulls. They wanted to prioritize Horace Grant’s development and you went to the Knicks. Did you ever have a problem that it seemed like the Bulls just got rid of you for someone else? Especially because you and Michael Jordan were so close?
I think Doug [Collins] was….The year before, I spoke up about a couple things. That’s probably why I got traded. But I always speak up for my teammates if they’re right, no matter what the situation is. I’m not gonna sit there and bite my tongue. I know how this guy rolls. When they traded me, I didn’t lose no sleep.
What did you speak up about?
We played the Knicks on Christmas Day. And Doug told us everyone could go home. But we lost, so he made everybody go back on the plane, but we all had [already] made plans from New York to go separate ways. He was real sensitive, so I guess he didn’t like the way we played. He rubbed a lot of guys the wrong way.
Soon as we got back from the Christmas break, we had a team meeting. So, we aired it out about everything, and that next year, three or four of the guys who aired it out weren't there. It was just one of those things.
When you got to the Knicks, you made the playoffs plenty of times. Pat Riley was an unbelievable coach and New York had a relatable, rough identity while y’all beat folks up in the paint. Did you ever feel a type of way because you didn’t win it all?
I definitely feel a type of way we didn’t win it all. I think we could have had three chances to get there, but we only got there once. We came out every night and played hard and played to our ability. Some nights we didn't score a lot of points, but our defense kept us in the games. But losing to Houston in '94 was a heartbreaker. We thought we were the better team. We took the lead 3-2, but they won two straight. I think that if we would've played some way differently [we would’ve won]. If Patrick would've passed the ball out of the double team, we had more options on the weak side. But you know, that's my point of view on that.
Do you blame Patrick Ewing for the Knicks losing that championship?
Blame? I think coaching got to be.... I think we had Rolando Blackman, Pat Riley wouldn't play him. I think the point guard calls the plays, and you get them from the coach. The coach calls the plays, now you got to make the plays. We didn’t make the right plays, or have enough plays from our best player to win.
So you don’t blame Patrick Ewing?
I mean…I’m not blaming him for getting the ball. Sometimes it just don’t go in. But the thing is, you gotta think of a second option sometimes. He didn’t go second option enough. And I blame that.
One of the most referenced people in your book is Charles Barkley. Over 100 times. It’s very clear that you do not rock with Barkley.
No, I do not.
So why did you “slap the shit” out of Barkley, as you write? [During the a lockout in 1998, Oakley was famously rumored to have punched Barkley in a hallway. Oakley says in the first sentence of the book that he didn’t punch Barkley: “I did, however, slap the shit out of him.”]
He’s just talking too much. He’s not trying to get nothin’ solved. He was just talking and being in the press like he does on TNT now. He said something about the Knicks, and I took it to heart. Even though we ain’t win nothin’, you ain’t gonna talk about the team that I rep and I’m around. I’m not having it. Barkley just kept talking and I told him, next time I see him, on point, I’m coming right up to him, and I got something for him.
And then you proceeded to slap the shit out of Charles Barkley?
Yes. Yes, I did.
Do y’all still have beef? You sort of laugh at him in the book because he lost his ability to be friends with Michael Jordan and LeBron James because he runs his mouth.
I don’t have no issue. He probably got an issue with me–“Why Oak always gotta talk about me?” Same way you get to talk about these young kids now, trying to make a living for themselves. You criticize them every night. So, why can’t somebody criticize you? You was an ass when you played. Great talent, but ask anybody he played with, he was an ass to play with. It was never teamwork. It was all about him. So, hey: It is what it is.
You describe more than a few skirmishes in the book. Let me run through some of them. In 2001, when you were on the Raptors, you fell out with Tyrone Hill over $20,000, and you hit him in the head with a basketball during a shootaround.
We didn’t fall out. He owed me some money and he didn’t pay me in time. He was trying to drag me around like it was okay. So, I had to let him know. Hey, you borrow money from the bank, they charge taxes. You don’t pay the IRS, they going to come and get you. So, I had to come and get him.
You also punched Jeff McInnis during another shootaround.
That last punch was from something else. He disrespected me. So I told him, same way I did Barkley, next time I see you, I don’t care if you’re in the White House or the outhouse, I’m comin’ to get you.
What happened with you and Dennis Rodman? Why’d you kick him out of a steakhouse on South Beach?
We did an appearance together that afternoon. He was cool before that, but we left the restaurant and he asked, “What you doing tonight?” And I said, “I’m going to my steakhouse. About 7, 7:30.” I do a couple of things. I stop by Prime 112. I get a call from my manager. He said, “Oak, guess what’s happening?” I said, “What?” He said, “Dennis is walking around eating off people's plates.” I said, “I’ll be right over.”
I walked over there, I look through the window and I’m looking at him, doing this. Wow, my agent was right. I made a beeline for him. I did him like I did Charles Barkley, I didn’t smack the guy. I just grabbed him by his shirt and asked him, “What the heck is you doing?” He said, “I’m just having a good time.” I said, "You don't have a good time like this in my type of establishment." I grabbed him, dragged him to the door and threw him out. I said, "Don’t you never come around me again."
Does Dennis still have beef with you? Has he cleared it up?
No! When he sees me, he goes the other way. Did you see “Bronx Tale,” when that guy owes that guy that money? Any time he sees him, he says, “I’m gonna pay you” and he runs the other way? That’s what Dennis does. I’ve seen him a couple of times, but he goes the other way. Dennis is soft. He was a good rebounder, but he was soft. When you need that much attention, and you got to do all that, something is wrong.
You mention that you’ve cooked for Oprah, Obama, and even Donald Trump. What’s your go-to dish?
It’s according to the settings you ask for. I don’t have a go-to dish. I am the go-to because I’m cooking it. It’s about what the room wants: gator for a barbecue, or for a kid’s cookout, they might want hot dogs, burgers, pizza. You might get some grown stuff, fish, sea bass, brussel sprouts, spring rolls. It’s all on the guest list.
My favorite line from the book is, “some guys like to talk shit, and some guys like to run and hide, but eventually I catch them.” You sound like a bounty hunter.
[Laughs.] Well, I mean, if you’re in my circle, I’m going to see you again. It’s just, do you want to come around me again? I’m not going to change my route for no one. Somebody says they looking for me? My brother always said, “If you ever hear somebody looking for you, go get them, don’t give them a chance.”
People like me for who I am, quiet as it’s kept. I’m consistent, and have been over my career for what I say and what I do. I don’t go pickin’ no fights. But if somebody bring it to me? Well, I gotta protect myself. The new generation likes my style…they’re the future. I’m glad they like how I carry myself. You gotta pass the torch and hope they carry it well.
