Charles Oakley may never have taken home a championship ring in his 19 years in the NBA, but he won the hearts of fans for the fierce style that made him a player described as “the friend you wish you had, and the enemy you wish you’d never made.” His nickname, Oak Tree, was a nod to his solid, immoveable presence on the court.
Though he may not have been in the spotlight quite like contemporaries Michael Jordan and Patrick Ewing, the 6-foot-8-inch power forward remains an immensely popular figure for his all-out approach—a drive born out of discipline and determination.
“I wasn’t the most skilled guy on the court,” he admits. “But I was tough-minded: you couldn’t just push me around. My understanding of the game got me to where I am. I just took it like a job… I didn’t cut corners. Some guys don’t have to go through all the practice, four or five hours a day. I probably had to.”
That attitude powered him through five stops on his NBA journey: the Chicago Bulls (with Jordan), the New York Knicks (with Ewing), the Toronto Raptors, the Washington Wizards and the Houston Rockets, earning an NBA All-Star selection along the way. Retired since 2004, he ranks 28th all-time in NBA appearances (1,282) and 23rd all-time in rebounds (12,205).
If grit was an important ingredient in Oakley’s success, so was his ability and willingness to adapt. “I wasn’t one of those guys who couldn’t adjust,” he says. “I adjusted my game to be more of a team player.” It’s about recognizing your situation, he says: “When you play with certain guys—a Michael Jordan, Vince Carter, Patrick Ewing—the ball was not gonna be in your hand so many times.”
It was also about knowing his part in the bigger picture. “When you play with superstars on your team and you are new to the team, my thing was I had to play my role, know my craft. I want to be on the floor, so I’m doing whatever it takes to be on the floor.”
Part of that drive came from joining the NBA from a small historically Black university (Virginia Union) rather than one of the bigger schools that typically fed the league. He had something to prove. “I had to really show that I knew how to play and that I understood the game. I played with a lot of guys on the All-Star team that went to a bigger school, but their IQ wasn’t like mine.”
“I want to be on the floor, so I’m doing whatever it takes to be on the floor.”
Having his say
Oakley supplemented his high hopes with hard work. “It wasn’t like you were going to outwork me. You didn’t have to call me to get up. You didn’t have to call me to be on time. I think I was late maybe twice in 18 years. I knew how to work.” Some players seem to need coaches to motivate them, but he feels that’s a weakness. “Because the coach ain’t out on the court when it’s time to make a decision; you’ve got to be IQ-smart enough to make it.”
How did he develop his team-player mentality? “Just being strong-minded, coming in knowing what you’ve got to do as a rookie.” Plus, letting the established players know that he wasn’t there just to back them up; he wanted their starting spot. “And when I bring that intensity every day in practice, some people can’t handle it.” Oakley also lists the importance of exhibiting discipline: “Being on time, doing stuff accurately, doing your craft on the court.” Keeping in mind that “people look at you just to see what you know.”
Over the course of almost two decades in the topflight, there were some changes to his game, of course. “My jump shot got better from college; my free throws got better.” But mostly, he was simply consistent, dependable. He mentions LeBron James, still playing at the highest level after almost 20 years. “He’s showing that, take care of your body and your mind and just know your craft, and you can do it.”
Oakley had his detractors during his playing days, but he didn’t pay them any attention. “They said bad things about me. ‘Oh, he doesn’t listen.’ ‘He this and that.’ But my thing is, not every road you go down is smooth. Some people are going to talk about you. Are you going to let them break you? They’ll talk about you and see, can you take it? Talking is what I do, but I don’t talk unless I have to. Some people talk just to be talking; I don’t.”
Oakley has spoken up and spoken out in print, however. His memoir, The Last Enforcer: Outrageous Stories from the Life and Times of One of the NBA’s Fiercest Competitors, released earlier this year. In it he brings his take-no-prisoners playing approach to recalling his career and some of his encounters with the game’s big names. “I wanted people to see my walk of life,” Oakley says of the writing project. “The gentleman I am and the guy that people see on TV, they’re two different people.” He hopes readers are encouraged to “speak your mind, don’t hold back, let ‘em have it” as he does in the book.
Oakley acknowledges that, without basketball, his life could have turned out very differently. Growing up in Cleveland with a single mom, “there was a lot going on in the streets,” he says. “I didn’t get in trouble like some of my [siblings], but I was in the mix of a lot of different things every day… some type of way I stayed from it.” There were a couple of occasions on which “I could have turned and went the other way but, knock on wood, I made it out.”
Oakley credits playing two sports—football, in addition to basketball—and having to take two buses each way to and from school with helping him stay busy (and out of trouble). He also had a job on the weekends. When he went away to college for four years, he says, a lot of his friends went away to jail. “They were getting 10, 15, 20 years.” Thankfully, now many of them are out and have made a better life for themselves, “but when we were growing up, it was hectic.”
“The coach ain’t out on the court when it’s time to make a decision; you’ve got to be IQ-smart enough to make it.”
Making his escape
Wanting to get away from the Cleveland scene played a big part in his choosing Virginia Union as a sought-after high school player. He visited a couple of other potential schools but chose the smaller Division II university in Richmond in part because it was eight hours from Cleveland, and he wanted to be somewhere that he couldn’t just drive home to on the weekend.
“I knew that it was time for me to get out,” he says, “because I knew, sooner or later, if you keep doing it wrong, this and that, things happen and it wasn’t going to happen for the better, it was going to happen for the worse.”
With that experience of his own, what advice would he offer to young men today? “Just try to keep struggling,” he says. “Keep some positive things in your life. Know that, at an early age, things are not easy. You’ve got to put something in to get something out.” Apply yourself, he says; go to college. Not everyone can play sports, but “be successful in the business world… a lawyer, a doctor, or some kind of politician. But grow up to be a grown man.”
It’s tough for parents these days, he believes, with all that’s available to kids on social media. Plus, many families don’t have grandparents or other relatives to keep an eye on the children while a single mom or dad works, like when he was young. “Kids now, they are watching themselves; sometimes they don’t have people in the house with them.” Get to know those you associate with inside and out, he says to young people. “People now are hanging with people they don’t know… they might be in a gang or something.”
Though his NBA days are long past, Oakley has remained in the sport. He was assistant coach for the Charlotte Bobcats for a spell and is currently coach for the Killer 3s in the three-on-three Big3 league founded by rapper and actor Ice Cube. Away from the game, he has been involved in various business ventures and become something of an in-demand chef, catering for private clients (Michael Jordan, Oprah Winfrey) and hosting the TV show Chopping it Up with Oakley.
How did Oakley become known for his cooking skills? As a self-confessed picky eater, he had a lot of questions when eating out while on the road. He started trying to prepare at home some of the things he ordered. “I learned technique; some food needs a lot of seasoning, some doesn’t. The timing: you can’t cook food up high. You can boil water up high, but you can’t cook your food up high.”
He learned about balance, about serving size, and how to keep the nutrition in vegetables. Then, just like with basketball, he kept practicing. “I played 19 years, so I should know what’s anything about the NBA,” he says. “So, with food, you stay with it, and that’s what I did. I stayed with it and there’s nothing I can’t cook now.”
Basketball and cooking may seem to be worlds apart, but Oakley sees some common threads in finding success in each discipline. It’s all about knowing your craft. “Basket-ball, you start playing as a kid, dribbling and shooting, but then once you get old enough, you define your skill level,” he explains. “In the kitchen, the same thing; you learn and ask questions. I’ll still ask questions, because in cooking there is always something to learn.”
That’s one thing that’s different: “In basketball, you can’t go but 90 feet [long] and 50-something across. When you are in the kitchen there’s always new dishes. Everybody is changing dishes around and cooking in different ways.”
CHARLES OAKLEY’S GUIDE TO COOKING A BETTER BURGER
Knowing his reputation for being as handy in the kitchen as he was on the court, WayMaker Journal asked Charles Oakley for his advice on how to serve up the best turkey burger, which can be notoriously difficult to get just right:
“You have got to season it—put a little Worcestershire sauce or something,” he advises. “Some people put mustard in it, some people put garlic, black pepper, a little sea salt. Some people can put a little steak sauce in it; anything that keeps it moist. And when you are cooking it, you don’t have to mash it; it’s just going to sweat. Turkey meat is hard to season sometimes; you have to know what you’re doing, especially when you’re doing lasagna, meatloaf.
“Cooking, it depends on how big your burger is. Some people like a quarter-pounder burger but I don’t make mine that thick. If I’m cooking them at home, say, four or five minutes a side, medium high. You don’t want to overdo it, because you are going to turn it over and cook it the same amount of time. Or some people might cook it two or three minutes on high and put it in the oven for five or six minutes and let it finish cooking, to get that sear.”
CHARLES OAKLEY’S PLAYER PICK
There’s no greater compliment for an athlete than to be compared to one of the all-time greats—hence the talk about “The new Michael Jordan” or “The new Shaq.” Which of today’s players would Charles Oakley describe as the new him?
“I don’t think anyone plays the way I played, but if I had to give the blueprint to anyone it would be Draymond Green [Golden State Warriors],” he says. “He’s not got the highest jump, he’s not the greatest shooter, but he brings that tenacity, he brings leadership, he brings toughness every night. People get down on him… but at the end of the day, he’s got four rings; a great career. He brings what his team needs; he makes it happen for the Warriors.”
From an interview with Louis Carr
