3. Michael Jordan & Charles Oakley (1986-87)
Before the addition of Pippen, the Chicago Bulls subjected Michael Jordan to some of the worst supporting casts and complementary role players in franchise history. Looking back, it’s incredible to think he managed to drag each and every single one of those teams to the postseason in the first place.
They weren’t all so bad, however, especially Charles Oakley, who stood tall above the rest when it came to providing the Greatest Of All Time help out there on the court. The second-year big man didn’t earn an All-Star selection until he was 30 years old despite averaging 14.5 points and 13.1 rebounds per game with the Bulls in 1986-87, but his presence as an enforcer made far more of an impact for this team than any award will tell you.
Michael Jordan and Charles Oakley were an all-time great Bulls duo before we even knew it.
Bouncing back from a broken foot in his sophomore season, Jordan was determined to put the league on notice, and he did just that. MJ earned his first of ten scoring titles in ’87, averaging a ridiculous 37.1 points per game, a mark he would never surpass again. This was the year that made everyone realize that Air Jordan was here to stay, and it was only a matter of time until he had the NBA in the palm of his hand.
Unfortunately, that wouldn’t materialize soon enough to help Oakley out, as the Bulls posted a meager 40-42 record and were swept by Larry Bird’s Celtics in the first round. As great as Jordan was, their inability to translate that talent to wins holds this duo back at No. 3 here. Oakley would be traded for Bill Cartwright and Will Perdue in 1988, the same year as Scottie Pippen’s rookie season. This move ultimately helped form the Bulls’ core for the first three-peat run, it’s just a shame Oakley couldn’t have also hopped along for the ride.