A star forward at Virginia Union, Charles Oakley was a first round 1985 NBA draft pick, he was chosen ninth by Cleveland and then traded to the Chicago Bulls, where he teamed with Michael Jordan until the end of the 1987-88 campaign. As a rookie Charles Oakley averaged 9.6 points per game and a robust 8.6 rebounds per game and helped the Bulls reached the 1986 NBA playoffs.
An aggressive rebounder, Charles Oakley looked after rebounds like he was entitled to them. In his sophomore NBA season, 1986 he led all NBA players with 775 defensive rebounds and also in total rebounds with 1,077. The next season he
led in both categories again, 740 DRB and 1,066 TRB, both years averaging over 13 ppg, and both years the Bulls made the NBA postseason playoffs. In his second year in Chicago, Charles Oakley scored 1,192 points in 82 games, a 13.1 ppg average, and posted a career best 296 assists.
Traded to the New York Knicks in 1989-90, Charles Oakley played 10 along-side center Patrick Ewing seasons in the Big Apple, averaging between 8.5 ppg and 12.12 ppg and pulling in on average 10 rebounds per game. In 1997-98 he posted a career high 123 steals in 79 games. Charles Oakley was a major defensive star and blocked 384 shots in his long career, and averaged 9.6 rpg, and 9.7 ppg in 1,275 NBA games. He helped his teammates reach the NBA postseason playoffs in 15 different seasons.