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Charles Oakley is helping charities raise money for summer hoops camps and rubbing elbows with other NBA icons

The league legend is heavily involved in Cleveland and Charlotte, but he’s not sure when he’ll go back to the Garden

To many people, Charles Oakley is living the American dream, the good life, and, in some parallel universe, it might be the perfect life.

A native of hardscrabble Cleveland, Oakley rose from All-American status at Virginia Union University, a historically black NCAA Division II university in Richmond, to become one of the most ferocious rebounders and reliable defenders in NBA history, having his best years with the Chicago Bulls and the New York Knicks.

Early in his NBA career, Oakley’s work ethic caught the attention of a young teammate on the Bulls who would go on to become one of the greatest basketball players on this planet.

That friend, Michael Jordan, was recently on one end of a phone call to help resolve a dispute between Oakley and New York Knicks owner James Dolan, when Oakley was tossed from Madison Square Garden after exchanging words with security guards.

Also on the call, from NBA headquarters in New York, were Oakley and NBA commissioner Adam Silver.

That’s what friends are for, right?

Oakley himself played the role of loyal friend last week, with an appearance in Charlotte, North Carolina, where Jordan currently owns the NBA’s Charlotte Hornets.

That’s when Hornets president and chief operating officer Fred Whitfield, another longtime Jordan and Oakley friend, held the 15th annual HoopTee Celebrity Golf Classic that brought 35 sports and entertainment celebrities to town to help raise funds for disadvantaged youths, a duty that means the utmost to their circle of friends.

HoopTee raises funds for the annual Achievements Unlimited Basketball School, now in its 33rd year; the funds help 75 percent of the nearly 200 campers attend for free, Whitfield said.

“Giving back is just a wonderful thing,” said Oakley, who added that he attends “12 to 15” similar events each year. “It’s important for the kids who can’t afford it. I just try to give them hope, just showing support and love, to help make themselves better in life.”

Oakley said he has been traveling annually to North Carolina since 1985, after becoming Jordan’s teammate on the Bulls and a few years after Whitfield founded Achievements Unlimited Basketball School in his hometown of Greensboro, North Carolina, with the help of Jordan, Ralph Sampson, Johnny Dawkins and David Henderson.

The camp, which has hosted more than 10,000 kids through the years, features speakers from an array of occupations who discuss success principles, with a heavy emphasis on education and resistance to drug abuse.

Oakley talked about why he believes the program has such staying power.

“It’s the body of work, the people who run it … the kids, the support from celebrities and entertainers, the people around the city, the fans,” Oakley said. “Giving back is just a wonderful thing. Fred tries to make a kid’s wish come true.”

Other celebrities who participated in activities included former NFL running back Eddie George, former Hornets and Miami Heat star Alonzo Mourning and NFL Hall of Famer Bruce Smith.

They come because they understand the objective, Whitfield said, which is reaching out to help kids from underserved neighborhoods.

“It’s really the kids,” Whitfield said. “I know that’s sort of a phrase that people say, but as I look back on 33 years that we’ve run Achievements Unlimited basketball school, when I look back on the succession of kids who weren’t good enough to be professional athletes, that have gone on to do great things — be doctors, lawyers, teachers, military personnel — those kids dream their dreams the same way NBA players do.

“This golf tournament is just a facilitator to help those kids have an opportunity they don’t ordinarily have. Most of our kids couldn’t afford to go to basketball camp anywhere, so we create that experience for them, and the only way to do it is the golf tournament, and the easy way to do it is to ask my friends in the NBA and the NFL and coach [Ron] Rivera [of the Carolina Panthers] and that type to just come in and support us.

“And they enjoy doing it because they understand what the long-term goal is, which is to give every kid that we can touch a chance at a better life.”

Several participants were alumni from Jordan’s University of North Carolina extended family, including former NFL defensive back Dre’ Bly and former NBA stars Antawn Jamison, Al Wood and Scott Williams. Still, Oakley might even trump all the Tar Heel family ties — he believes he is the only athlete to perform the trifecta with MJ.

As far as Oakley knows, he is the only player to be teammates with Jordan on both the Bulls and the Washington Wizards. Plus, he was an assistant coach with the Bobcats-Hornets organization.

“I’m the prize in his Cracker Jacks,” Oakley joked. “I got all three of the Jacks.”

Oakley said he also participates in similar activities in New York, Chicago, Alabama and in Cleveland, where he hosts several events, including a community dance.


In Cleveland, Oakley has several businesses, some of which he runs with family members, including a car wash, laundromat and nail salon. He also owns businesses in the New York area and other cities. A longtime lover of cooking, Oakley sometimes works as a caterer and has appeared on the TV show Chopped.

All that, plus he has resumed coaching as part of the inaugural BIG3 basketball league. And he has not ruled out stepping onto the court to play.

“I just try to keep my hands in a little bit of everything,” Oakley said. “In this world, people have to realize, you have to find yourself, where you fit, and try to stay in your lane.”

A confluence of fortunate events seems to be occurring in his life.

The street in front of his alma mater, John Hay High School, was recently named Charles Oakley Way. Oakley is also a member of the Virginia Sports Hall of Fame and the CIAA Hall of Fame.

These days, Oakley’s hometown, Cleveland, is in the midst of another renaissance, this one prompted by the emergence of many millennials’ pick as the greatest basketball player: LeBron James, Oakley’s homeboy from down the road in Akron, Ohio.

James helped the city break its championship jinx, winning the 2016 NBA title, and has taken the Cavaliers to the Finals for three straight seasons. And the Cleveland Indians were one game away from winning baseball’s World Series last fall before eventually losing to the Chicago Cubs in Game 7.

Oakley was an invited guest in James’ box for a World Series game.

“At least the city got one ring,” Oakley said. “It would have been great if Cleveland had had two parades in one year.”

Who else in the world has such familial links to two of the best basketball players in the universe?

So, when will Oakley return to a Knicks home game?

“I just left New York; they weren’t playing,” he said, adding a chuckle to punctuate the response.

“I don’t know. … That’s a billion-dollar question. …

“Would you go back in the Garden?” he turned the question back to the reporter.

Maybe in the good life. Maybe in the American dream.

Maybe, somewhere in the universe, Oakley makes a triumphant return to Madison Square Garden.

But on this planet … he’s not saying.

He’s just living the life.

David R. Squires is a writer, editor and digital journalist who has worked for the New York Times, Detroit Free Press, Cleveland Plain Dealer and St. Petersburg Times. He's also a former editor-in-chief of BlackVoices.com and BVQ magazine, a former Black Enterprise writer and editor and NUTribemagazine.com managing editor.