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In the history of the NBA, every legend had a right-hand man. For Michael Jordan, it was without question, Scottie Pippen. The two may not be on the best terms today, but as a tandem, they won six championships together. However, Pippen wasn’t the first guy to be the running mate for MJ. Before the success of the Chicago Bulls, there was one man who was willing to stand up against anyone to protect His Airness: Charles Oakley. The former New York Knicks forward was Chicago’s elite rebounder for a stretch of three seasons.

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After a dominant stint in Virginia Union, Oakley got his ticket to the NBA. While many see it as a privilege to have their dreams come true, for The Oak there was no choice. While in conversation with NBA Hall of Famer Kevin Garnett, the 59-year-old spoke about watching his mother move cities and ‘grind’ just to stay above the surface.

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Before pairing up with Michael Jordon, Charles Oakley watched his mother scrap and work hard

Oakley recently sat down on ‘KG Certified’ to discuss his life. He spoke about a multitude of topics from playing with Jordan to his life before the NBA. The former Chicago Bulls forward is the youngest of six children. Hailing from Alabama, Charles Oakley’s life was far from the one he made for himself. As a youngster, he had to watch his mother come to Cleveland with nothing but a few items.

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Narrating his story, Oakley told The Big Ticket, “She came from Alabama to Cleveland. She didn’t have nothing but her bag, shoes, couple of outfits. So she had to come in and get on the grind. Finally got a job with my uncle who had a bar.”

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Watching his mom work through multiple jobs was enough to motivate Oakley to take basketball seriously. In his senior year at Virginia Union, The Oak would establish himself as one of the best forwards averaging ?24.3 PPG & 17.3 RPG. He was also named the National Player of The Year, and from there it was NBA bound.

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As soon as he was selected by the Bulls in 1985, Oakley would begin his stellar 19-year NBA career. However, his priority was to set up his mother to live comfortably. The 59-year-old bought his mother her very own house once he was in the league which he says, “you should as a kid if you get the money to finance”.?

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Watch this story:?5 times Charles Barkley and Shaquille O?Neal have had heated fights on Inside the NBA

Much like his mother, Oakley was a protector. Not only did he dominate the glass but he stood tall for his teammates, in particular Michael Jordan. The duo became close friends in their short time together. History will always remember The Oak for who he was to the Bulls, the shadow that would fight and brawl anyone when it came to his teammates.

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Written by

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Anuj Talwalkar

4,483 Articles

Anuj Talwalkar is a senior NBA Newsbreak specialist at EssentiallySports, trusted for his real-time coverage and fast, accurate updates on league developments. With five NBA seasons and two Olympics coverages under his belt, Anuj stands out as the go-to reporter for the NBA Matchday Newsdesk. As part of the EssentiallySports Journalistic Excellence Program, he continuously refines his hard reporting with grounded storytelling shaped by fan culture and court-level insights. An economics graduate and lifelong OKC fan since the Supersonics era, Anuj combines analytical thinking and a genuine passion for basketball. He’s recognized for both his live news coverage and feature writing, with aspirations to someday interview Russell Westbrook. Anuj’s reporting is marked by its reliability, depth, and strong connection to the pulse of the NBA.

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Arijit Saha

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