Pippen spent the next four seasons with Portland, with his best season coming in his first year. He was the leader of the team that finished 59-23, good enough for second best in the league behind Pacific Division champ Lakers. The two teams would also meet in the Western Conference Finals.
After going down 3-1, the Trail Blazers forced a Game 7 and held a 15-point fourth quarter lead in the decisive game. But a miraculous comeback by the Lakers sent them to the Finals where they eventually won the NBA title.
The Blazers would make the postseason in each of the next three seasons that Pippen was in a Portland uniform, but an assortment of injuries reduced the amount of time he spent on the court. His versatility remained an asset though, as in his last season in Portland he became the starting point guard and led the Blazers on a 21-5 streak.