Even though he’s been retired for almost 20 years, Michael Jordan still dominates the spotlight. But that’s not the case for his ex-teammate, Charles Oakley. Once the league’s ultimate enforcer—tough, fearless, and a rebounding machine—Oakley made a name for himself playing for some of the NBA’s most respected franchises. But now, instead of making headlines for hard fouls or locker room stories, Oakley’s name has surfaced in a completely different way—and fans didn’t see this one coming.
Angela Oakley debuted on The Real Housewives of Atlanta Season 16 this March, and fans were excited. Charles Oakley comes across seems proud and supportive too—writing on Instagram, “Congratulations, [Angela] you have my love and support.” On a recent episode, viewers were hit with a bombshell: the Oakleys are reportedly sitting on $2 million in debt after flipping five investment properties that they’re now struggling to sell.
Angela, 44, opened up about their real estate struggles during the May 11 episode. “So I own five investment properties,” she explained. “Most of them are ready for the market. It’s just that the price that we are positioning them at hasn’t been the most welcoming to the market, because I haven’t sold any of them yet.”
In a televised confessional, she admitted. “I’m in debt $2 million, so I am in some deep sh– with these houses,” Angela admitted. When fellow Housewife Kelli Ferrell swung by to check out one of the properties, she casually asked when it would hit the market. “It’s about to hit the market in the next 10 days,” Angela said. Kelli Ferrell, another cast member on the show, raised her eyebrows. But the surprises didn’t stop there.
Jul 2, 2017; Charlotte, NC, USA; Killer 3s coach Charles Oakley looks on during the game against Power at Spectrum Center. Mandatory Credit: Jeremy Brevard-Imagn Images
Behind the scenes, during an inspection of one of the five properties, Ferrell didn’t hold back. “I mean, the ceilings are a little low. The kitchen is nice. I mean, it’s cute, don’t get me wrong,” she said. Then came the kicker—the pool was dry, and the closets were barely there. “Angela, the pool don’t even have no water in it,” Ferrell pointed out, sounding more confused than concerned.
Still, Angela stayed optimistic. “Don’t beat me up too bad!” Angela admitted, “I am desperate to unload these houses,” revealing she listed the home at a wild $3 million. “I don’t know, girl. I don’t know if you’re gonna get $3 million for this,” Ferrell said.
Both women joined RHOA this March alongside Brit Eady. However, currently there is no update on the sales. But the question is-
Can Michael Jordan’s ex-teammate overcome this debt?
To assess Oakley’s outlook, let’s first examine his NBA earnings and business holdings. Long before the debt headlines and reality TV appearances, Oakley was making serious money on the court. Drafted 9th overall by the Cavaliers and later traded to the Bulls, Oakley spent his early years battling alongside Michael Jordan. He even returned to the Bulls in 2001 for one last run. According to Celebrity Net Worth, he made about $6.5 million during his final year there and pulled in nearly $7.19 million total in Chicago.
Not only that, Oakley made big bucks during his Knicks days—around $16.4 million—while helping the team consistently reach the playoffs. Then came his time with the Raptors, where he raked in another $21.2 million. Add a cool $1 million with the Wizards and a final stint with the Rockets in 2004, and you’re looking at a career haul of nearly $45.6 million.
Even after hanging up his sneakers, Oakley didn’t slow down. He pivoted to business, opening ventures like Hair Solutions and Nails EtCetera in his hometown of Cleveland. His sister Carolyn reportedly runs the place, keeping it in the family.
But his biggest win? The car wash hustle. Oakley’s Wash House now runs in several cities—including Brighton Beach in New York. Plus, he’s behind Red, The Steakhouse, with locations in Cleveland and Miami. Thanks to these business plays, Oakley has built a post-retirement net worth of around $12 million.
So yeah, if we’re being real, Oakley’s in a tight spot—but with that kind of cash behind him, bouncing back might just be a matter of time.
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