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Charles Oakley spent 19 years in the NBA protecting his rim and some of the game’s marquee stars. Just ask him. With open mouth and clenched fists, he cleared space for Michael Jordan and helped form the spine of the Knicks for a decade.
Now 59, Oakley is a coach in the BIG3 league, an author of the newly released “The Last Enforcer,” and a philanthropist, most recently through his “Oak Out Hunger” campaign. Now he’s a “guardian of responsible gamblers,” said Martin Lycka, Senior Vice President of American Regulatory Affairs and Responsible Gaming at Entain.
It’s a seemingly unusual collaboration. But with each plate of food that he and his charity have handed out since 2020, Oakley has learned the many different ways that people are hurting. That’s why Entain Foundation US sponsoring Oakley’s traveling soup kitchen during March – which is not coincidentally National Problem Gambling Awareness Month – made so much sense to him. Oakley’s personal gambling history is as titillating as would be expected of a friend of Michael Jordan. But he makes it clear this effort is about personal responsibility and safeguarding younger potential gamblers.
PlayUSA chatted with the outspoken Oakley between stops in New York in Nashville, among many topics, on doing – not donating, responsible gambling, how sports betting is changing sports, and taking out Shaq in a boxing match.
Charles Oakley on responsible gambling, hunger, history and more
How did Oak Out Hunger and the collaboration with Entain begin?
Charles Oakley: For many years, I’ve been doing a lot of charity work – probably over different a hundred different charities over the last 10 years – just doing stuff positive out in the community, in Cleveland, Chicago, New York, L.A. Especially, Skid Row. This comes from the heart, from the family, from generations, from my grandparents, my mom, how she used to give back to people in the city we grew up in.
Once I got into the league, I saw, after a shootaround, just walking around you see people just need food, need somebody to give a meal or buy ’em a hot chocolate or buy ’em some tea or something. And I used to give people $20 and $30. They’d be sleeping. They’d wake up, it would be a surprise of the day.
We just try to show a lot of love, give back, go to the inner city, go back to these cities. All-Star weekend in Cleveland, we went down to The Mission. We cooked for like 750 people. And our goal is once we cook for certain cities on this tour, we’re going to go back and refurbish a basketball court in the neighborhood. We’ll try to put a hoop in the park.
I think that from playing all my years in the NBA, protecting all the legends on the court, I wanted for the new generation, for this Wager Score and Oak Out Hunger to be something positive, not just something that we do one time and just leave it alone.
I started doing TikTok because the young generation, they’re leading us in a different way. They bring the energy back to older people. And I think that the Wager Score is something real positive we’re doing. It’s letting kids know you can be responsible. Because gambling can get out of hand and go different ways and lead to bad things. And we’re just trying to jump on it.
We don’t see other outlets doing what we’re doing, trying to get some positive, going out to the younger generation before it gets started. Because everybody’s tuned into something as they get older in life, if it’s going out, hanging out, if it’s betting on scores, betting on games.
Oak Out Hunger, we’re doing all that in one. We’re trying to educate people. We’re trying to feed people. We’re trying to show ’em that we can be responsible, and you have to be responsible too.
How do you choose the communities where you take Oak Out Hunger?
Charles Oakley: We know everybody needs it. I think right before the pandemic kicked off, we had done New York, Cleveland, Chicago, Nashville. And so as we go, we add on. Some places that have some connection, we try to keep the bus rolling, keep the tour rolling.
We’re not trying to exclude someone. We hope one day that we can, in the whole year’s time, do 30-40 cities. But right now, we’ve just got to go with who’s on the team with us.
Does the current-generation active athlete give back enough?
Charles Oakley: It’s just like Ukraine. They want people on the ground. They want people to be there. You always can give back. You can call and write a check.
But I think that when you can go and be when people are present, they can see your face, your body language, you can feel what they’re going through on a regular day basis, I think that’s the most important thing. I think that’s what we’re doing.
We’re not trying to skimp over what we’re doing. We’re just trying to let you see that we’re doing it from the heart. Because, like I said, somebody can take $10,000, go feed a group of people. No. We’re doing the cooking, we’re doing all the paperwork, we’re doing the communication. And we’re getting to hear a lot of these people’s stories on hand.
What’s the overlap between hunger and problem gambling?
Charles Oakley: Entain understands we’re new to the game. But in life, you have to learn what’s going on, know what’s going on. So I think that we’re all older. We see people, and we see things going on, in so many ways, that kids could get strung out on gambling. And they don’t know.
A lot of kids, like my stepson, [it’s] ‘Gimme the credit card. I need to something for Roblox’ or something. They’ll not just to that time. They’ll ten times a month. You get your credit card, and it’s like, ‘I thought you said just one time?’ That’s $3-4,000 out.
So it’s more of a detail-control or responsible gambling site. You can go to a Wager Score if you’re having a problem, and they can show you how you can get back on track for your finances.
What are the logistics are setting up your food kitchen on the road?
Charles Oakley: They have to have the setup, and they let us know, and we tell ’em what type of kitchen we need and the space we need. And we go get the food, Sam’s Club, Restaurant Depot.
In Philly, we’ll probably do 150 people. New York, it’s a small venue: 150 people, so we’ll do breakfast and lunch. So when we go to Nashville from there, it’s going to be a different story, probably be 500 people for breakfast and maybe another 500 for lunch. We’re going to do a barbecue.
For Super Bowl, we had 800 people. So I had some assistance. We did 12 trays of macaroni and cheese 10 trays of chili. We did 10 trays of salad. So we had turkey burgers. We had hotdogs, we had chicken. So we had enough food to accommodate everybody.
I always try to have size, especially when you get the lunch and dinner, some kind of vegetables. We had string beans. You always want to tell them, ‘Gotta eat some vegetables during the course of a day.’
But when we do the breakfast, we do French toast, potatoes, regular bacon, turkey, bacon, pork bacon. We would give ’em an apple side, on the tray, and probably orange juice or milk.
How much do you get from the interactions with the people you’re helping?
Charles Oakley: The funny thing about it, when they come through the line, and we serve, they’ve all got different thoughts of mind. Some people are just glad to have it. ‘Thank you. Pray to God.’ Some people want to stop to talk to you. And some people … It’s just funny. I mean, they can keep you going. It can keep you like, ‘wow,’ it’s a lot of stuff out here.
People need health. They’re talking about their mental health. There’s a lot of people out here that might look like they’re good to go, and two blocks later, you might see ’em talking to themselves, just depressed. So you can get a lot by just being on the line.
We do serve ’em, too. Twelve-hour shift. … I want ’em to feel, I want to feel their vibe. That’s who they want. I was talking to a lot of people on Skid Row, when we first did that about five years ago, their main thing was like, ‘We get a lot of people to drop food off. We never see ’em again.’
I played basketball with them. I help clean the court off and I show ’em ‘I’m one of you right now.’ I want you to be happy when I leave here.”
Why do the tough guys always seem to be the softies once they stop playing?
Charles Oakley: Well, some people get arrogant and cocky, and that’s what the sexy players are. Your hard-working players never stop working hard. Now, I consider that me. My job is never over. I was all about work. I don’t want to be in a cute situation. … It’s good to be some time.
Are you surprised pro leagues have embraced gambling?
Charles Oakley: It’s all about the dollar. Everybody getting paid money. And once the NBA started sponsoring liquor, maybe about five, six years ago, I knew …. liquor and gambling go together. And just like they said they’d never move professional teams in Vegas…
The NBA will probably have a team there in the next 3-5 years because you got hockey, you got football, you will definitely get a baseball team. So the NBA, you don’t want to be left out. It’s a copycat brand, especially with money involved.
Should active athletes be endorsers for sportsbooks?
Charles Oakley: They just caught the football player, Calvin Ridley. … When you allow people to be in this type of conversation, you have no control over the guy 24 hours a day. I heard he had opened a site up with his name.
This is a trippy slope. Maybe they should have more retired players than players who are playing.
The money is pulling everybody in there. You see so many people doing it now. So the way we are doing it, at least we are out here in the community trying to give back in a way and teach people that yeah, you can be responsible, because the new generation, that side, that’s our future.
So if they mess up, we mess up. So we want them to be responsible. And hopefully, wait until you get 21, not before 21, to start gambling.
Did you really challenge Shaq and Charles Barkley to a boxing match?
Charles Oakley: Yeah. I assume they said no.
Because you would take them both?
Yeah. Well, in different matches. I think so. I like myself. It’s just funny, I just came out with a book, “The Last Enforcer.” It’s got a lot of stuff in this book. I’m riling people up. So I’m ready. I’m ready for them to give me a date and time. I’ll be there. It’s a lot of fun when you write a book. I ain’t scared of saying the truth. So it’s a lot of good stuff in this book.
Me and Shaq have had words before, and Barkley and I had words. We had a lot of words.
Barkley did my first chapter of the book. It’s all about Barkley. That should have been about Isaiah [Thomas]. I’m going to wait until the next book for him in there.
What NBA players would you pay to see play?
Charles Oakley: Ja Morant got the hype right now. [Stephen] Curry, LeBron [James], the league is just different now. Most of the older players really, I don’t think they tune in like they used to because the dynamic of the game now, so many threes, and you don’t have to be structured anymore to play.
You see, so much bad stuff happens on the court, and you look at the LA team, they got four Hall of Famers, and they’re 10 games under .500.
Do you like modern basketball?
Charles Oakley: The ball still has got to go through the hoop. I mean, you can change, and you can shoot 3s [3-pointers]. You can shoot 35% 3s every night. The ball’s still gotta go in. So just know what you can do and what you can’t do.
I think Memphis is showing teams that you can grow as long as you play within your team. Phoenix, same way, two teams that the last two or three years, gelled late. They don’t have three great superstars, but they have players who can play together.
In this April 30, 1998, file photo, Miami Heat’s Alonzo Mourning, right, and New York Knicks Charles Oakley grapple as Knicks coach Jeff Van Gundy holds on to Mourning’s leg during a fight in the closing seconds of Game 4 of a first-round NBA basketball playoff game at Madison Square Garden in New York. The Heat and Knicks renew an old playoff rivalry on Saturday in Miami. (AP Photo/Mark Lennihan, File)
Have you seen ‘Winning Time: The Rise of the Lakers Dynasty’?
Charles Oakley: No, I haven’t. Since ‘The Last Dance,’ it’s going to be kind of hard for someone to make a documentary, a series, something to come behind that. I know a guy has the ‘Blood in the Garden’ book out. I had a book out, Scottie [Pippen] had a book out. So a series … it’s going to be tough.
The Lakers had something that nobody ever had. They had Showtime. They had Magic and LA. He had one of the probably greatest owners ever, Dr. [Jerry] Buss. So they’ll get a lot of attention. But Magic is doing a sitdown like ‘The Last Dance, right?’ [Editors note: Yes]
Well, Magic likes the spotlight. I’m quite sure he’s getting a lot of money from this. Magic doesn’t do something just to be doing it.
Do you ever see yourselves in documentaries and have your recollections of events changed?
Charles Oakley: I think if they got it on film, [you] did it. I don’t really question myself. I don’t tend to go back and look over too much stuff.
How important has it been for you to find the next thing to do in retirement?
Charles Oakley: You have to keep building in life. You have to put yourself out there. I mean, I know a lot of people write movies, do movies, they do this and that. The script sounds good until you put it together.
My script ain’t together all the way yet. But I’m still working to get it finished.
Remaining #OakOutHunger Tour Schedule
March 25th: Philadelphia, PA Lutheran Settlement House
April 1st: Nashville, TN: Room in the Inn
