The Power Forward started 30 Games as a rookie, where he was an All-Rookie with 9.6 Points and 8.6 Rebounds per Game.  Oakley proved immediately that he was the toughest man on the court, and he made sure that no cheap shots would be taken on Michael Jordan.  He made significant strides in his production in his next two seasons with double-double averages; 14.5 Points and 13.1 Rebounds in 1986-87 and 12.4 Points and 13.0 Rebounds in 1987-88.  In both of those seasons, Oakley was the league-leader in total Defensive Rebounds and was second in Rebounds per Game.

After the 1987-88 Season, the Bulls made a bold move to trade Oakley to New York for Center, Bill Cartwright, as they felt that Horace Grant could fulfill the duties at Power Forward.  The Bulls were proven right, and Oakley went on to be a bigger star with the Knicks.   He returned to Chicago briefly for a year in 2001.

As a Chicago Bull, Oakley had averages of 10.6 Points and Rebounds per Game.