Rise to Success: Career Highlights of Charles Oakley

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By Popular Timelines Editorial Team  · Updated:
Charles Oakley

Discover the career path of Charles Oakley, from the first major opportunity to industry-changing achievements.

Charles Oakley is a retired American professional basketball player, primarily known for his formidable presence as a power forward in the NBA. He spent a significant portion of his 19-year career with the New York Knicks, where he established himself as a premier rebounder and defensive player. Oakley also played for the Chicago Bulls, Toronto Raptors, Washington Wizards, and Houston Rockets. Since retiring from the NBA, he has transitioned into coaching, currently leading the Killer 3's in the BIG3 basketball league.

1985: Drafted by Cleveland Cavaliers and traded to Chicago Bulls

In 1985, Charles Oakley was drafted 9th overall by the Cleveland Cavaliers in the NBA draft, but his rights were traded to the Chicago Bulls.

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March 15, 1986: Career High in Points Scored

On March 15, 1986, Charles Oakley scored a career-high 35 points in a loss to the Milwaukee Bucks.

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April 26, 1987: Postseason Career High in Points

On April 26, 1987, Charles Oakley scored a postseason career-high 25 points and grabbed 15 rebounds in a loss to the Boston Celtics.

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June 1, 1994: Game 5 Eastern Conference Finals

On June 1, 1994, Charles Oakley recorded 12 points, 13 rebounds, and 7 assists in Game 5 loss against the Indiana Pacers during the Eastern Conference Finals. The Knicks won the series.

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1998: Traded to Toronto Raptors

In 1998, Charles Oakley was traded from the New York Knicks to the Toronto Raptors.

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January 7, 2001: Career High in Blocks

On January 7, 2001, Charles Oakley achieved a career-high with 6 blocks, also recording 12 points, 10 rebounds, and 7 assists.

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2001: Traded to Chicago Bulls

In 2001, Charles Oakley was traded by the Toronto Raptors back to the Chicago Bulls for Brian Skinner.

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2002: Second tenure with the Bulls

In 2002, Charles Oakley played his second tenure with the Chicago Bulls.

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2002: Signed with Washington Wizards

In 2002, Charles Oakley signed with the Washington Wizards, reuniting with former teammate Michael Jordan.

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2003: Final NBA season

2003 marked Charles Oakley's last season in the NBA.

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March 18, 2004: Signed with Houston Rockets

On March 18, 2004, Charles Oakley signed the first of two 10-day contracts with the Houston Rockets.

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2007: Attempted NBA comeback

In 2007, at age 44, Charles Oakley attempted an NBA comeback, with several teams reportedly interested.

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December 26, 2010: Hired as Assistant Coach

On December 26, 2010, Charles Oakley was hired as an assistant coach for the Charlotte Bobcats.

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December 1, 2011: Left Assistant Coach Position

On December 1, 2011, Charles Oakley left his position as an assistant coach for the Charlotte Bobcats due to health issues.

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2017: Coaching the Killer 3's

In 2017, Charles Oakley became the coach of the Killer 3's team in the BIG3 basketball league.

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