In this interview on The Draymond Green Show, Draymond Green talks with former NBA forward Charles Oakley about his early experiences with a young Michael Jordan after being drafted 9th overall by the Chicago Bulls. Oakley describes meeting Jordan during a pre‑training‑camp pickup game, the rapid development of a friendship that included Jordan taking Oakley to the All‑Star weekend in Dallas and writing the foreword to Oakley's book. Oakley then recounts his trade to the New York Knicks, where he embraced the role of an enforcer and defensive anchor, explaining how he approached match‑ups against Jordan by protecting the paint and forcing Jordan to adapt his jump shot. The conversation shifts to parallels with Draymond’s own relationship with LeBron James, emphasizing that these bonds are rooted in business, respect, and competition rather than personal animosity. Oakley and Green both stress that on‑court battles are separate from off‑court friendships, framing the dynamics as a professional “business” where winning is the priority, followed by a handshake after the game.
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What's up everybody? It's Draymond Green. Make sure you subscribe to the Volumes YouTube channel below so you don't miss any more of this great content going forward. But I also wanna get into some of your playing career.
Right.
And obviously that was being drafted the 9th overall pick by the Chicago Bulls.
Right.
Which means you then cross over with a very young Michael Jordan. What was your first impressions of Michael Jordan at that time when you first saw him? Obviously we know what he became, but what was those, your thoughts then?
You know, coming from a historic Black college and getting drafted in the top 10, like you said, my eye was just, "Hey, come in, work, work, work." You know, and then when I got a chance to meet him, we was playing pickup and it was August right before training camp. You know, guys come in early, whatever. And you know, he was always about business. And I was, like I said, there doing my craft and working on my game and showing them I wanted to be there. And some type of way, training camp started, we just seemed to get closer and closer. And next thing you know, you know, we started just hanging, hanging. He took me to All-Star in Dallas, took me under his wings, and we've been tight ever since. And if you look at the book, you know, he did the foreword, you know? So hey, it's still, we still jiggling. Yeah.
Absolutely. Which is incredible. Not many people can say they could get a foreword from Michael Jordan, man. That's insane.
Yeah. That's like winning a Grammy. I mean, winning an award, an Emmy or something. So—
Absolutely.
Hey, it's good to have a friend like that. And I know you got a lot of them. I know when you do write your book, you gonna have a great person do the foreword. I already know. I appreciate it. You in good space with a lot of good players.
You then, you get traded from the Chicago Bulls to the New York Knicks. Now, whereas you've built this relationship with Michael Jordan, y'all are like this. As an enforcer in the type, in the way you play, how was that then playing against Mike? You gotta lay Mike out when he come to the hole and he not stopping.
Nah, well, you know, I tell everybody, you know, once I got traded to New York, my attitude was to change no matter who I was playing against. I had to do the same thing. Play defense, clog the middle, and let 'em know that it's still, You can't come down the lane, I'm still here. So we didn't have no problem. He took it as business. He took it as every day, you know, I'm going to war. And when we played against the Bulls, I didn't see him that much. He shot a lot of jump shots. So my game was the same. You come in the paint, Mike, no. You know, I used to practice against him sometime. No matter. If Jersey's opposite color come, I gotta step up. And that's my job, take charge of it. Mm-hmm. And, you know, defense. My defense, I was the anchor in New York, and we had a real good defense. So I was in the top 5 and everything. So Michael worked on his jump shot once I got traded, 'cause he knew that he had to pull up. He had to pull up. So in his book, you know, he talk a lot of trash about, "Yeah, I was born the wrong time." But yeah, you know, hey, he knew if he came down that lane, he was gonna have to pay a toll.
I like to think, a guy who I have a similar relationship with, who's a big brother of mine, who taken me under his wing and not only on the court, but in business and life off the court. Also a nephew of yours, LeBron James. I think he had to work on his goddamn jump shot when I came in this league too now.
Right.
No, but I think, you know, there's always been, I totally understand that. 'Cause there's always been this thing made of me and LeBron. And I mean, even before I signed with Klutch, you know, like, And then I signed with Clutch. Like, how can Draymond sign with Clutch? They hate each other and this, that, and the other. And the reality is we've never hated each other. Maybe when I first came into the league, like my first year or two.
It's complicated.
'Cause you're fighting for respect. But it was never a lack of respect thing. It was just more of a, I don't know you, you don't really know me. But we quickly got to know each other and we've been building a relationship since. And people, they can't wrap their head around it. How does these guys play? Or LeBron drives, Draymond fouls him hard. Me getting suspended from a game with a situation with LeBron, all of these things. And people can't really wrap their head around it.
And I always say— Well, sometimes it ain't for people to, you know, hey, you know the deal, LeBron know the deal. Like they said, with me and Mike, I mean, it's business. You know, you trying to win just as LeBron trying to win. Mike wanna win, I wanna win. So at the end of the day, shake your hand and go separate ways.
