Pippen immediately became part of Chicago's young forward tandem with 6'10" power forward Horace Grant, though both came off the bench to back up Brad Sellers and Charles Oakley, respectively, during their rookie seasons. Still, Pippen claimed the starting small forward position during the 1988 playoffs with his stellar play, helping the Jordan-led Bulls reach the Eastern Conference semi-finals for the first time in over a decade. Pippen continued to improve, helping the Bulls to the Conference Finals the following year as well as 1990, when he earned his first All-Star berth. In 1991, he continued to establish himself as a force to be reckoned with, undoubtedly the Bulls' second best offensive and defensive player after Michael Jordan. He helped lead the Bulls to six NBA World Championships (1990-91, 91-92, 92-93, 95-96, 96-97, and 97-98).
Pippen became known for stellar defense in addition to his consistent scoring, earning several all-defensive team nods, including several on the first team. In 1992, he was named to the original Dream Team which competed in the Summer Olympics in Barcelona. 1994 marked Pippen's coming out party, when he stepped out from Jordan's shadow and became known as one of the best players in the league. That year he earned All-Star Game MVP honors. In 1995, he had perhaps his best season, leading the Bulls in scoring, rebounding, assists, and the entire league in steals. For his efforts, he earned the second of three straight all-NBA first team nods, and was a strong candidate for MVP.
After playing in Chicago for 11 seasons, his tumultuous relationship with General Manager Jerry Krause came to a head, and the second alltime leader in points, assists, and steals in Chicago's history was traded to the Houston Rockets for the lockout-shortened season in 1998-99. In Houston, he teamed with Hakeem Olajuwon and Charles Barkley to form one of the best front lines in NBA history, but the squad lacked chemistry. He was traded in the offseason to the Portland Trail Blazers, who he led to the Western Conference Finals, where they lost to the eventual champion, the Los Angeles Lakers, in seven games. Pippen was a consummate playoff performer, reaching the playoffs an amazing 16 straight years (11 with Chicago, 1 with Houston, 4 with Portland) and played in more playoff games than anyone but Kareem Abdul-Jabbar. In the summer of 2003, new Bulls General Manager John Paxson (and former Pippen teammate) decided to change the fortunes of the rebuilding Bulls by bringing Scottie back to the Windy City, where he counts on Pippen's skills to lead the team back into contention.
Pippen is also famous for having pioneered the point-forward position, which he popularized with his dominant play for over a decade.