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Charles Oakley: An Enforcer’s Odyssey

Last Updated: October 17, 2022
The iconic power forward and NBA All-Star dicsusses his new memoir, The Last Enforcer, on the latest edition of “Boardroom Book Club.”

Charles Oakley is a fundamental force of time and space, not unlike winds, tides, and gravity. For two decades in the NBA, he utterly was who he was — a stout, rugged presence at the power forward position whose contributions as a defender and rebounder on his come-up with the Chicago Bulls made him the chosen enforcer for none other than Michael Jordan.

A trade sent him to the New York Knicks in 1988, breaking up an irresistible duo just before the Bulls became a dynasty under Phil Jackson. But while a championship was not ultimately in the cards, Oak’s legacy defined itself over the course of a decade under the lights at Madison Square Garden that included an All-Star appearance and an Eastern Conference Title in 1993-94.

Now approaching 20 years removed from the last game of his career, Charles Oakley is ready to tell his story with a new memoir, The Last Enforcer. And to get the inside story on occasional belligerent moments with Charles Barkley, the iconically physical nature of the 90s Knicks, his enduring brotherhood with MJ, and the impact of George Floyd and the march for social justice, we sat down with Oak for the latest edition of “Boardroom Book Club.”

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SAM DUNN: You’ve been retired from basketball for a while now. Why was now the perfect time to write this book?

CHARLES OAKLEY: Just wanting to tell my story. Playing the league 18 years, a lot of stories, a lot of different things [happened], and I just wanna let ’em know [about] the enforcers.

SD: The league is a lot different from the way it was when you played. Was The Last Enforcer always going to be the title of the book?

CO: Yes, it’s me. It’s my makeup.

I get a lot of my toughness from my grandfather. I talk about this in the book, how he was tough, enforced things. When he was coming up, he’d bring a lot of people with him — you know, “enforcer” is not a bad word. It’s not a bad name. So I named this book The Last Enforcer [for the] way I played and who I stand for. Being a leader. So I fit the description.

SD: You mention your grandfather in the book. Who were some of your other inspirations on your path to understanding what it means to be an enforcer?

CO: Neighborhood people. My high school basketball coach. My college coach, Dave Robbins, he was the real guy. I went to a historically Black college and we had a white coach — so he made it through because we was in a conference that had one white coach out of 14 teams and he won championships.

When I was coming [up], just my uncles and people and I see every day day in life. I got a lot from a lot of different people in my upcoming.

SD: Who were the basketball players who exemplified this enforcer attitude as you came up?

CO: [Maurice] Lucas, Lonnie Shelton, some of the big power forwards. Buck Williams was a small power forward, but he was a tough guy.

Once I got to the league, my thing was I had to find my own way. And I had to pick something that I can do and do it every night for 82 games, and [that] hard work was defense, rebounding, taking charges, and the [enforcer] name came as I showed my game.

SD: One of the starring characters of the book is Michael Jordan. How did you come to be so close, and what do you think he saw in you so early on?

CO: The work ethic, something my grandfather did — people watch you and they see what you do. And when I came into the league, it was always [arrive] early work hard, stay late, on time doing the plays.

And in my rookie year, [Jordan] took me to the All-Star game in Dallas. He showed [me] a lot. But I was just a guy who I stayed in my place. Never tried to outdo no one.

SD: You’re still friends with Michael to this day?

CO: Yeah. Oh, yeah. When I was, when I was doing this book, we finished the book and we talked about, ‘We need someone to do the foreword.’ We came with three or four names. I said, ‘I got one name. I’m gonna call my guy.’ He answered the phone. He said, ‘Okay, just gimme a week or two. I’m gonna get it back to you.’

We’ve been friends. We talk about it in a book, how we came up, how we’d eat McDonald’s [for] every practice back in the day. We built that brotherhood, and to this day, it’s still there.

I told him, ‘I think I literally led [the NBA] two years in a row in rebounding out of my whole career. I think if I got 12,000 rebounds, he probably got 4,000 outlets from me. So it was just one of them things — I used to feed him the ball, and every now and then, somebody will throw you a bone. So he threw me a bone and [wrote] the foreword for this book. Just helped the book out.

SD: Another character that makes important appearances in the book is Charles Barkley. You start the very first chapter out with a story about slapping him upside his face. What went into the decision to begin Chapter 1 that way?

CO: It’s like basketball with four quarters — you need four main topics to make the book. I got 270 pages, so every 65, 70 pages is something that’s gonna jump out to you. So Barkley was the first character. Maybe [it’s] Tyrone Hill, maybe Judge Mathis. At the end, I talk about Michael and LeBron.

But Barkley, you know, it happened in the game and in the book. He smacked me on my chin, turned down the wrong street. There was an alligator and I bit him.

On the court, I didn’t care how much talent he had. We both wore the same number. We both play the same position. So some [of] that’s probably why we didn’t get along. But he’s a character in this book. So when you read this book, you might get the point [that] we still don’t get along.

SD: So you don’t have any kind of relationship with Charles Barkley?

CO: No. I mean, we’ve been in the same room several times, but I’m quite sure he kept his eyes on me, but I didn’t keep my eyes on him.

SD: Another important player here is Frank Isola. What ultimately made him the guy you wanted to work with on this book?

CO: We went through a process, had five different writers, talked about each writer, [and] I think out of all the writers, we came down to two. [Frank] had an advantage because I know him from writing over the last 30 years, and he’d been around the Knicks and I felt comfortable with him because he knew a lot [that] went on.

He can relate to it more than a lot of other people because he’s been in it. We’re homegrown. So we picked him, [and] I think he did a great job. In this book, I really liked how he put it together.

SD: What changed when you were traded from the Bulls to the Knicks?

CO: I’m like a mailman. It’s the same address. It’s still the same game. So I gotta do the same thing; I’m just on a different team.

And once I got traded New York, I’m like, I’m in a better space, but we didn’t win. [The] only thing I wish — that [we] would’ve won for the fans, because they really came out. They love the game of basketball and they like when you play hard and give effort. We didn’t win the championship, but we showed up every night.

SD: What do you think was the single best Knicks team you played on?

CO: I’m gonna say ’94 was the best because that’s when we went to the Finals, but we didn’t win. I talk about it in the book. It’ll tell you a lot about the Knicks and about myself. Just the mindset we showed up to play [with] every night, we played with heart. The fans kept encouraging the way we played and what we did. They wanted to win a championship, but we didn’t win it, but they say, you know what? Y’all gave your heart every night. That’s just important to them.

In this book, we talk about it, because the fans walk around the city and they just give you all the love.

SD: You also talk about what became a strained relationship with the franchise and with James Dolan. What’s the current state of things there after what played out at MSG in 2017?

CO: Unfortunately, it happened. We’re still in litigation right now. I’m gonna just play it out. I would love to do something for the fans one day and just make everybody happy. I’ve been willing to do that from day one, so we’ve got this way to see my side. We’ve been ready to make amends.

SD: I know that New York would absolutely love that. As we close, what’s the, one thing you would most like people to take away from reading The Last Enforcer?

CO: Just knowing me over my career; the consistency I’ve [had] as a person and the consistency in this book. This book will make you happy, give you some laughs, and that’s what all fans want. They want something to cheer for.

The Last Enforcer is available now from Simon & Schuster wherever books are sold.

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About The Author
Sam Dunn
Sam Dunn
Sam Dunn is the Managing Editor of Boardroom. Before joining the team, he was an editor and multimedia talent for several sports and culture verticals at Minute Media and an editor, reporter, and site manager at SB Nation. A specialist in content strategy, copywriting, and SEO, he has additionally worked as a digital consultant in the corporate services, retail, and tech industries. He cannot be expected to be impartial on any matter regarding the Florida Gators or Atlanta Braves. Follow him on Twitter @RealFakeSamDunn.