Considered one of the greatest small forwards of all time, Pippen played an important role in transforming the Bulls into a championship team and popularizing the NBA around the world during the 1990s.

Pippen is a two-time inductee into the Naismith Memorial Basketball Hall of Fame, once for his individual career and once as a member of the "Dream Team", having been simultaneously inducted for both on August 13, 2010.

Playing point guard, he led his team to the state playoffs and earned all-conference honors as a senior, but was not offered any college scholarships.

Pippen began his college playing career at the University of Central Arkansas after being discovered by the school's head basketball coach, Don Dyer, as a walk-on.

[16] As a senior, his per game averages of 23.6 points, 10 rebounds, 4.3 assists, and near 60 percent field goal shooting earned him consensus NAIA All-American honors in 1986 and 1987, making him a dominant player in the Arkansas Intercollegiate Conference, drawing the attention of NBA scouts.

Pippen claimed the starting small forward position during the 1988 NBA Playoffs, helping the Jordan-led Bulls to reach the conference semifinals for the first time in over a decade.

[23] In the 1990 Eastern Conference Finals, Pippen suffered a severe migraine headache at the start of Game Seven that impacted his play, and he made only one of his ten field goal attempts as the Bulls lost 93–74.

[24] In the 1990–91 NBA season, Pippen emerged as the Bulls' primary defensive stopper and a versatile scoring threat in Phil Jackson's triangle offense.

[25][better source needed] He had his first triple-double on November 23 when the Bulls faced the Los Angeles Clippers as he had 13 points, 12 assists and 13 rebounds in 30 minutes in a 105–97 win.

The Bulls (with key additions of Toni Kukoč, Steve Kerr and Luc Longley) finished the season with 55 wins, only two fewer than the year before.

Pippen, who had been the Bulls' leader all season long in Jordan's absence, was so angered by Jackson's decision to not let him take the potential game-winner that he refused to leave the bench and re-enter the game when the timeout was over.

[29] Although Kukoč did hit the game-winner, a 23-foot (7 m) fadeaway jumper at the buzzer, there was little celebrating by the Bulls, as television cameras caught an unsmiling Phil Jackson storming off the court.

Still, Pippen finished the 1994 season leading the Bulls in every major statistical category—points, rebounds, assists, steals, and blocks—joining Dave Cowens (1977–78) as the only players in NBA history to accomplish the feat; Kevin Garnett (2002–03), LeBron James (2008–09), Giannis Antetokounmpo (2016–17) and Nikola Jokić (2021–22) have since matched it.

[41] Pippen scored a career high of 47 points in a 134–123 win over the Denver Nuggets on February 18, going 19–27 from the field and adding 4 rebounds, 5 assists, and 2 steals in 41 minutes of play.

With only seconds remaining and the outcome safely in Chicago's favor; Jordan collapsed into Pippen's arms, creating an iconic image of the pair that has come to symbolize "The Flu Game".

After eleven seasons with the Chicago Bulls, Pippen, the franchise's second-place leader in points, assists, and steals, was traded in January 1999 in a sign-and-trade deal[53] to the Houston Rockets in exchange for Roy Rogers and a second round pick in the 2000 NBA draft (Jake Voskuhl).

[54] In order for the Rockets to create enough salary-cap room to acquire Pippen, Charles Barkley said that he sacrificed greatly as he signed a five-year $67.2 million contract before the previous season.

[59] Pippen had his second triple-double of the season in a 106–101 loss against the Los Angeles Clippers, posting 23 points, 10 assists, and 10 rebounds in addition to 6 steals in 45 minutes of play.

[55] Pippen was traded to the Portland Trail Blazers on October 2, 1999, in exchange for Stacey Augmon, Kelvin Cato, Ed Gray, Carlos Rogers, Brian Shaw and Walt Williams.

However, led by the All-Star duo of Kobe Bryant and Shaquille O'Neal, the Lakers managed to erase Portland's lead and win the game 89–84 and with that also the series.

[71][72] After undergoing a procedure to remove a bone fragment in his right elbow, he made his return on February 22 against the Utah Jazz and played for the remainder of the season.

[74] Pippen played for two more seasons in Portland: the Trail Blazers made the playoffs both years, but were eliminated in the first round each time, in another sweep to the Lakers and in a 7-game series to the Mavericks, respectively.

The team played against the Los Angeles Lakers that night and Pippen was reunited with Phil Jackson, Michael Jordan, Dennis Rodman, and Horace Grant during the ceremony.

[86] In his third game of the tour, Pippen registered 21 points, 12 rebounds, six assists and two steals in 30 minutes in a 102–74 Sundsvall Dragons win over Akropol of Rinkeby.

According to NBC Sports Chicago, he and the Bulls could not come to an agreement on compensation and allowing him to keep his role of making regular TV appearances on ESPN's The Jump.

Gifted with extraordinary athleticism, even when compared with other professional athletes, Pippen demonstrated substantial skill in multiple areas well-suited for basketball.

Several NBA players, including Jordan,[94] Jason Kidd,[95] and Karl Malone[96] have placed Pippen in their all-time starting lineups.

Pippen and Michael Jordan both attended and participated in the celebration, where they were reunited with their former teammates John Paxson, Horace Grant, Stacey King, Craig Hodges, Will Perdue, Scott Williams, Cliff Levingston, Dennis Hopson and Assistant Coach Johnny Bach.

[119] Shortly after retiring, Pippen learned that his financial adviser Robert Lunn, who he claimed had been recommended by the Bulls, was under investigation for bank fraud.

[121][122][123] On July 11, 2013, Camran Shafighi filed a $4 million lawsuit against Pippen in Los Angeles Superior Court over an incident that had occurred on June 23 at the restaurant Nobu in Malibu, California.