If you followed basketball through the late ’80s and ’90s, there’s no way you missed Charles Oakley. Known as one of the toughest and most respected players on the court, Oakley, who turned 62 in 2025, built an impressive NBA legacy—and a net worth of approximately $12 million. But Oakley’s journey has been far from ordinary. His life after basketball has been marked by controversy, entrepreneurship, and even reality TV through his family connection. Here’s a deep dive into how Oakley crafted his wealth, reputation, and life beyond the hardwood.

From Cleveland to NBA Stardom

Charles Oakley was born on December 18, 1963, in Cleveland, Ohio. Oakley wasn’t just another kid dreaming of making it big; he was determined. After excelling at John Hay High School, he took his talents to Virginia Union University. There, he dominated on the court, amassing an impressive 2,379 points and 1,642 rebounds, leading his team to a near-perfect 31-1 season in 1985 and winning the NCAA Division II Player of the Year.

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Bulls, Knicks, and Becoming an NBA Icon

Oakley’s NBA journey began in 1985 when he was drafted by the Cleveland Cavaliers but quickly traded to the Chicago Bulls. It was there, alongside a young Michael Jordan, that Oakley established himself as a fearless protector on the court—earning a reputation as an “enforcer.” His rookie contract earned him just $75,000, modest by today’s standards, but his contributions were priceless.

However, it was after his trade to the New York Knicks in 1988 that Oakley truly became an NBA household name. Playing alongside Patrick Ewing, John Starks, and Mark Jackson, he helped the Knicks dominate the Eastern Conference. The peak of this era was undeniably the 1993-94 season when the Knicks reached the NBA Finals, narrowly losing to the Houston Rockets. Oakley’s rugged defensive play and relentless rebounding made him a fan favorite and earned him substantial paydays, culminating in career earnings of around $43.6 million.

Veteran Presence in Toronto and Beyond

In 1998, Oakley took his veteran experience north, joining the Toronto Raptors, mentoring younger stars like Vince Carter and Tracy McGrady. His highest annual salary of $8.75 million came during his time in Toronto in the 2000-2001 season. Though past his prime, Oakley was still impactful, notably achieving a career-best six blocks in a single game in 2001.

After stints back with the Chicago Bulls, Washington Wizards, and briefly with the Houston Rockets, Oakley finally retired from professional basketball in 2004, concluding his NBA career with over 12,000 points and rebounds—a testament to his enduring toughness and consistency.

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Post-NBA Life and Entrepreneurship

Oakley’s post-NBA life didn’t slow down. Instead, he transitioned into entrepreneurship, leveraging his earnings into several successful businesses. In his hometown of Cleveland, Oakley launched family-run enterprises like Hair Solutions and Nails EtCetera salons, as well as Oakley’s Wash House—a unique combination car wash and laundromat. He also owns multiple car wash and detailing businesses across New York, reflecting his strategic move into practical, community-centered enterprises.

But entrepreneurship wasn’t his only endeavor. Oakley stayed connected to basketball through coaching, briefly serving as an assistant for the Charlotte Bobcats in 2010 and later coaching the Killer 3s in the BIG3 basketball league, showcasing his passion for mentoring new generations.

A Controversial Relationship with the Knicks

Charles Oakley’s post-playing days haven’t been without controversy. A highly-publicized incident in 2017 dramatically shifted his relationship with the New York Knicks organization. Oakley, who had been openly critical of the Knicks’ management, got into an altercation at Madison Square Garden involving owner James Dolan. He was forcibly removed from the arena and subsequently arrested. Although charges were relatively minor, the incident cemented a frosty relationship with the Knicks, one that sadly remains unresolved, with Oakley reportedly still having to pay for his own tickets to games.

Family Life and New Ventures

On a brighter note, Oakley’s personal life has offered him stability and renewed visibility. He married Angela Reed in 2016, and as of 2025, Angela has stepped into the spotlight as a cast member on Bravo’s hit reality show, “The Real Housewives of Atlanta.” This new chapter has given fans a fresh glimpse into the Oakley household, introducing Charles to an entirely new audience.

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Oakley’s Enduring Legacy

Today, Charles Oakley’s legacy is a blend of gritty NBA heroics, savvy business decisions, and a touch of reality TV glam. Despite controversies, he remains beloved by fans who remember his fierce competitive spirit and unwavering toughness on the court. His $12 million net worth in 2025 stands as proof of his disciplined financial planning and diversified career moves post-retirement.

Whether you’re a longtime NBA fan or discovering Oakley through reality TV, one thing’s clear—Charles Oakley continues to make his mark, both on and off the court.