Pippen played high school basketball but stood just 6 feet 1 inch upon graduation. However, he had grown 2 inches by the time he entered the University of Central Arkansas, where he initially served as manager of the basketball team before earning a spot on the roster. By his senior year, he was 6 feet 7 inches tall and was the team’s best player. In 1987 the Seattle SuperSonics selected Pippen in the first round of the NBA draft and traded him to Chicago. During his rookie season (1987–88), he became a regular in the Bulls’ lineup. Pippen possessed a notably multifaceted skill set: his size and strength served him well under the basket, while his ball-handling skills and shooting touch made him a threat from the outside. On defense, his long arms and quick footwork made him an imposing force and helped Pippen earn selection to the NBA’s All-Defensive first team eight times over the course of his career.
When Pippen arrived in Chicago, he was overshadowed by teammate Michael Jordan, who already had been an All-Star in each of his first three years in the NBA. Playing alongside possibly the greatest player of all time, Pippen nevertheless began to draw attention for his own stellar play and was named to the first of seven career All-Star games in 1990. Pippen was a key contributor to the Bulls’ three consecutive NBA championships from 1991 to 1993, and, with Jordan’s retirement after the third title-winning season, Pippen became the primary star on the team. He led the Bulls to a 55–27 record during the 1993–94 season and was named to the All-NBA first team, but his first season in the spotlight was marred by his refusal to re-enter a crucial playoff game with 1.8 seconds remaining because coach Phil Jackson diagrammed the final play to go to another player. Pippen was again in the All-NBA first team in 1994–95, but his dominance and Jordan’s late-season return to basketball were not enough to advance the Bulls past the second round of the playoffs. Pippen and Jordan were joined by a forward Dennis Rodman before the 1995–96 season and the trio guided the Bulls to another three straight NBA titles (1996–98).
With Jordan’s second retirement and Jackson’s departure from the team, the Bulls entered into rebuilding mode and traded Pippen to the Houston Rockets in 1998. The following year, he was traded to the Portland Trail Blazers, where he had four fairly productive seasons, though no longer at an All-Star level. Before the start of the 2003–04 season, he signed again with Chicago but played only 23 games owing to injuries. In 2004 he retired from the NBA. Pippen won two Olympic gold medals playing for the U.S. men’s basketball team, including a stint as a member of the famed "Dream Team" at the 1992 Olympic Games in Barcelona. He was named one of the 50 greatest players in NBA history in 1996, and he was inducted into the Naismith Memorial Basketball Hall of Fame in 2010.