Scotty Maurice Pippen was born in Hamburg, Arkansas, on September 25, 1965, the son of Ethel (1924-2016) and Preston Pippen (1920–1990). He has 11 older siblings. His mother was 6 ft (180 cm) tall and his father was 6 ft 1 in (185 cm), and all of their children were tall, with Pippen being the tallest. His parents could not afford to send their other children to college. His father worked in a paper mill until suffering from a stroke that paralyzed his right side, prevented him from walking, and affected his speech. Pippen attended Hamburg High School. 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.

He 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. He did not receive much media coverage because Central Arkansas played in the NAIA, while the media focused on the more prestigious NCAA. Pippen stood only 6 ft 1 in (1.85 m) tall when he graduated from high school, but experienced a growth spurt while at Central Arkansas and grew to 6 ft 8 in (2.03 m). 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 1987 and made him a dominant player in the Arkansas Intercollegiate Conference, drawing the attention of NBA scouts.

Having eyed Pippen before the 1987 NBA Draft who was initially selected at No. 8 overall, the Chicago Bulls manufactured a trade with the Seattle SuperSonics that would send Pippen, selected fifth overall, to the Bulls, in exchange for Olden Polynice and future draft pick options. Pippen became part of Chicago’s young forward duo with 6-foot-10-inch (208 cm) power forward Horace Grant (the 10th overall pick in 1987), although both came off the bench to back up Brad Sellers and Charles Oakley, respectively, during their rookie seasons. Scottie made his NBA debut on November 7, 1987, when the Chicago Bulls opened against the Philadelphia 76ers. He finished with 10 points, 2 steals, 4 assists, and 1 rebound in 23 minutes of play, and the Bulls won 104–94. With teammate Michael Jordan as a motivational and instructional mentor, Pippen refined his skills and slowly developed many new ones over his career. Jordan and Pippen frequently played one-on-one outside of team practices, simply to hone each other’s skills on offense and defense. 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. Pippen emerged as one of the league’s premier young forwards at the turn of the decade, recording then-career highs in points (16.5 points per game), rebounds (6.7 rebounds per game), and field goal shooting (48.9%), as well as being the NBA’s number three leader in steals (211). These feats earned Pippen his debut NBA All-Star selection in 1990. Pippen continued to improve as the Bulls reached the Eastern Conference Finals in 1989 and 1990, but were eliminated both times by the Detroit Pistons. In the 1990 final, Pippen suffered a severe migraine headache at the start of Game 7 that impacted his play and he made only one of his ten field goal attempts as the Bulls lost 93–74.

Pippen has been married twice, first marrying Karen McCollum in 1988. They had a son named Antron (born 1987) before divorcing in 1990. He married Real Housewives of Miami star Larsa Younan in 1997. They had four children named Scotty Jr. (born 2000), Preston (born 2002), Justin (born 2005), and Sophia (born 2008) before divorcing in 2018. Scotty Jr. is a freshman on the basketball team at Vanderbilt University. Sophia appeared on the first season of Dancing with the Stars: Juniors. Pippen also has a daughter named Sierra (born 1995) with his former fiancée Yvette De Leon, and a daughter named Taylor (born 1994) with his former girlfriend Sonya Roby. Taylor’s twin sister, Tyler, died nine days after birth. Taylor played volleyball at Southern Illinois University, and now works as an accountant in Chicago.

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’. Alongside the help of Michael Jordan, Pippen continued to improve his game. 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. He had his second triple-double against the Indiana Pacers on December 22 as the Bulls defeated the Pacers 128–118. Pippen finished the game with 18 points, 11 assists and 10 rebounds in 41 minutes of play, in addition to 1 steal and 1 block while shooting 54.5% from the field. Pippen scored a season-high of 43 points on February 23 in a 129–108 win against the Charlotte Hornets. In addition, he also grabbed 4 rebounds, dished out 6 assists and had 6 steals in 31 minutes of play. He had a career-high field goal percentage that game with 94.1% as he was 16–17 from the field. Pippen had his third and final triple-double of the season on April 4 against the New York Knicks as the Bulls won 101–91. He finished the game with 20 points, 12 assists and 10 rebounds in addition to 4 steals while shooting 50% from the field in 42 minutes of play. The Bulls finished the season with a record of 61–21. They were first in the Central Division, first in the Eastern Conference and second overall, as the Portland Trail Blazers clinched the first spot. Pippen was second on the team in points per game with 17.8 and steals with 2.4 next to Michael Jordan and he was also second in rebounds per game with 7.3 next to Horace Grant. Pippen led the team in blocks per game with 1.1 and assists per game with 6.2. He ranked fifth overall in the NBA in steals, both for total and per game. For his efforts in the 1990–91 NBA season Pippen was awarded NBA All-Defensive Second Team honors. The Bulls went on to defeat the Los Angeles Lakers in the 1991 NBA Finals.

On September 21, 1991, amongst 9 other players (2 more would be later selected), Pippen was announced as a member of the United States men’s Olympic basketball team which was set to represent the United States of America in the 1992 Summer Olympics in Barcelona.

In order to commemorate the 20th anniversary of their first NBA Championship in 1991, the Chicago Bulls organization honored the 1991 Chicago Bulls Championship team in a ceremony during halftime of a game versus the Utah Jazz on March 12, 2011. 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. Former head coach Phil Jackson did not participate but gave a speech via a video message. Former Bulls’ broadcaster Jim Durham emceed the halftime ceremony.

He helped lead the Bulls to their first three-peat, as they won the following two years in 1992 and 1993. Pippen earned 10 NBA All-Defensive Team nods, including 8 on the first team. In 1992, he was named to the original Dream Team which competed in the Olympics in Barcelona, Spain. With the U.S. winning the gold medal, Pippen and Jordan became the first players to win both an NBA championship and an Olympic gold medal in the same year.

However, one of the most controversial moments of Pippen’s career came in his first year without Jordan. In the 1994 NBA Playoffs, the Eastern Conference Semifinals pitted the Bulls against the New York Knicks, whom the Bulls had dispatched en route to a championship each of the previous three seasons. On May 13, 1994, down 2–0 in the series in Game 3, Bulls coach Phil Jackson needed a big play from his team to have any chance of going on to the conference finals. With 1.8 seconds left and the score tied at 102, Jackson designed the last play for Toni Kukoč, with Pippen instructed to inbound the basketball. 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. 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. “Scottie asked out of the play,” Jackson told reporters moments later in the post-game interview.

The Bulls opened 1996–97 NBA season with a 17–1 record and had a league-best record of 42–6 when entering the All-Star break. Both Pippen and Jordan were selected among the NBA’s 50 Greatest Players as part of the league celebrating its 50th season. The ceremony was held at half-time of the 1997 NBA All-Star Game, which took place on February 9, 1997. Phil Jackson, the Bulls’ head coach, was honored as one of the 10 greatest coaches in NBA history, while the 1992 Chicago Bulls Championship team and the 1996 Chicago Bulls Championship team, on which Pippen had played a key role, were selected as two of the Top 10 Teams in NBA History. In the All-Star game itself, Pippen was 4–9 from the field, finishing with 8 points as well as 3 rebounds and 2 assists in 25 minutes of play. The East defeat the West 132–120 and Glen Rice was crowned the All-Star Game MVP.

After 11 seasons with the Chicago Bulls, Pippen, the franchise’s second all-time leader in points, assists, and steals, was traded in 1998 to the Houston Rockets in exchange for Roy Rogers and a 2nd round pick in the 2000 NBA draft (Jake Voskuhl). Pippen’s trade to Houston for the lockout-shortened 1998–99 season received much publicity, including his only solo cover of Sports Illustrated. 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. Pippen’s salary was $11 million, almost four times what it had been the previous season with the Chicago Bulls, $2.775 million.

After the 2002–03 season, Pippen left Portland to sign with the Chicago Bulls, where he had begun his NBA career and won six championships. The Bulls’ general manager John Paxson pursued Pippen to return to his old team, which had had little success following the breakup of the Bulls dynasty in 1998. The deal was made official on July 20, 2003, as Pippen signed a two-year, $10 million contract with the franchise. Pippen assumed a veteran role on the team in order to guide the young Bulls team, but was faced with numerous injuries throughout the season and was only able to play 23 games, averaging 5.9 points, 3.0 rebounds and 2.2 assists per game. He played the final game of his NBA career against the Seattle SuperSonics on February 2, 2004, scoring two points, with one rebound and three assists in eight minutes of play in a 109–97 loss. The Bulls compiled a 23–59 record, failing to qualify for the playoffs. This marked the first time in Pippen’s career that his team did not reach the playoffs. Pippen had been a constant presence in the NBA playoffs prior to this season, reaching the playoffs in 16 straight years (11 with Chicago, 1 with Houston, 4 with Portland). He is second in the NBA in career playoff steals with 395 (LeBron James leads with 445). On October 5, 2004, Pippen announced his retirement.

Alongside Barkley, his former Olympic teammate and future NBA Hall of Famer, Pippen joined Hakeem Olajuwon, but on-court chemistry problems emerged, especially with Barkley. Pippen had his first triple-double in a 93–87 loss against the Atlanta Hawks as he had 15 points, 10 rebounds and 11 assists in addition to 1 steal in 46 minutes of play. On April 22, 1999, Pippen was detained by police on suspicion of driving while intoxicated. The charges were later dropped due to insufficient evidence. 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. Despite averaging a career high in minutes per game with 40.2 and finishing 4th in the NBA in minutes played, Pippen’s scoring was down to 14.5 points per game, his lowest since his rookie year, and he made a career-low 43.2 percent of his shots. However, he also averaged his exceptional combination for a small forward of 6.5 rebounds and 5.9 assists per game, and was named to the NBA All-Defensive first team for the 8th time. The Rockets finished the season with a 31–19 record, third in the Midwest Division and fifth in the Western Conference. They faced the Los Angeles Lakers in the first round of the playoffs. In game 3 of the series Pippen scored 37 points and had 13 rebounds, 4 assists, and 1 block in staving off elimination. The Lakers went on to win the series the following game, defeating Houston 98–88.

Following the season’s end and the Rockets’ early elimination from the playoffs, Pippen expressed a desire to be traded. Charles Barkley appeared on Up Close and openly criticized Pippen, saying, “For him to want to leave after one year, it disappointed me greatly. The Rockets went out of their way to get Scottie and the fans have treated him well, so I was just disappointed in him.” Pippen responded by saying, “I wouldn’t give Charles Barkley an apology at gunpoint. He can never expect an apology from me. If anything, he owes me an apology for coming to play with his fat butt.” He stated that the main reasons for his departure were Barkley’s selfishness and his lack of desire to win. He also expressed the wish to play for his former coach Phil Jackson, who was now coaching the Los Angeles Lakers. Pippen said one of the reasons he wanted to play for Jackson was that he longed to return to the system in which they won six NBA titles together in Chicago. Pippen was traded by the Houston Rockets 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.

The Chicago Bulls retired Pippen’s jersey number in a ceremony on December 9, 2005. 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. Pippen’s 33 joined Michael Jordan’s 23, Bob Love’s 10, and Jerry Sloan’s 4 as the only numbers retired by the Bulls.

In 2007, Pippen had attempted to make an NBA comeback as he expressed that he would like to play for a championship contender in hopes of getting his 7th Championship ring. Pippen had spent the winter working out in Fort Lauderdale, Florida and announced that he was hoping for a late-season return to the league. Dwyane Wade, who was the Finals MVP of the 2006 NBA Finals and the captain of the returning champions, the Miami Heat, liked the idea of Pippen making a comeback and expressed his views on it: “I’m already playing with [Gary] Payton and Shaq, two guys I used to play with on video games. To add Scottie Pippen to the mix, that would be crazy.”

In January 2008, Pippen made a brief comeback to professional basketball at age 42, when he made a tour of Scandinavia and played two games for top Finnish league team Torpan Pojat (ToPo), and top Swedish league team Sundsvall. In his first game, on January 4, Pippen scored 12 points in ToPo’s 93–81 win over Porvoo. He registered nine points and nine rebounds in a 98–85 win over Honka on January 5. 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. The Dragons paid Pippen $66,000 for his appearance.

Pippen returned to the Bulls on July 15, 2010, as a team ambassador. In 2012, he was named senior advisor to Michael Reinsdorf, the Bulls’ president and COO.

On March 17, 2011, the Chicago Bulls organization announced that they would honor Pippen with a bronze statue which will be placed inside of the Bulls’ home arena, the United Center. He expressed his gratitude by saying: “Words really can’t express my feelings. It’s something you dream of as a kid growing up, but you can never foresee those childhood fantasies becoming reality. You see statues of individuals who have done great things and made their mark on history, but as a basketball player, you never really think about arriving at this point. It’s an amazing honor for the Chicago Bulls to do this for me.” The statue was unveiled on April 7, 2011, during a half-time ceremony of a game between the Chicago Bulls and the Boston Celtics.

On May 27, 2011, Pippen generated a great deal of criticism by saying that Miami Heat star LeBron James may be a better player than Michael Jordan. This came only a day after the Heat beat the Bulls 4 games to 1 to advance to the 2011 NBA Finals. Pippen said, “Michael Jordan is probably the greatest scorer to ever play the game. I may go so far as saying LeBron James may be the greatest player to ever play the game.” Pippen faced a backlash from Bulls fans after his comments, and even former teammates such as Horace Grant, who stated in a radio interview, “Wow, Pippen’s my man, and we’ll always be close, but I totally disagree. LeBron is going to be one of the top players to ever play the game, but Michael Jeffrey Jordan, who we bumped heads at times, is I think, the best basketball player I’ve ever seen.” In a later interview on the radio show Kap & Haugh, Pippen stated, “No, I did not say I would take LeBron over Michael. The reality is you need to go back and figure out what I said.”

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. Shafighi said that he was physically attacked by Pippen after taking pictures of Pippen inside and outside the restaurant, and was then taken to a hospital. On August 27, the district attorney’s office announced that charges would not be filed against Pippen.

Pippen developed a reputation for being a poor tipper at restaurants, earning him the nickname “No Tippin’ Pippen”. Shortly after retiring, Pippen learned that Robert Lunn, a financial adviser whom he claimed had been recommended by the Bulls, was under investigation for bank fraud. He had invested over $20 million through Lunn, who was sentenced to three years in prison in March 2016 on multiple fraud counts, including one count of forging Pippen’s signature on a $1.4 million loan that Lunn used to pay off personal debts.

On April 16, 2020, Pippen stated that he had been dismissed as a public relations ambassador for the Bulls in February. According to NBC Sports Chicago, he and the Bulls could not come to an agreement on compensation and allow him to keep his role of making regular TV appearances on ESPN’s The Jump. He quipped, “I didn’t really want it to be out in the public but I’m no longer employed by the Bulls. Probably is a good thing, right? I like to associate myself with winning.”