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On April 16, 2020, according to Pippen, he was dismissed in February as a public relations ambassador for the Bulls. 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". Pippen said, "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?" He also said, “I like to associate myself with winning.”

Pippen developed a reputation for being a poor tipper, earning him the nickname "No Tippin Pippen." Shortly after retiring, Pippen learned that a financial adviser, whom Pippen claimed had been recommended by his team, was under investigation for bank fraud. Pippen had invested over $20 million through the adviser, Robert Lunn. In March 2016, Lunn was sentenced to three years in prison on multiple fraud counts, including forging Pippen's signature on a $1.4 million loan that Lunn used to pay off personal debts.

On offense, Pippen relied primarily on his remarkable athleticism to gain an advantage over his defender; he slashed towards the basket for higher percentage shots. Early in his career, Pippen was not an adept jump shooter; he struggled when shooting directly on a line to the basket. He favored shooting his jump shots—mid-range and three-pointers—on an angle. He could regularly bank the ball off the backboard into the basket. He honed his jump shot over the course of his career and became more effective at scoring from distance later in his career.

A key play occurred in the following Game 5 which changed the outcome of the series. With 2.1 seconds left in the fourth quarter, the Knicks' Hubert Davis attempted a 23-foot (7 m) shot which was defended by Pippen, who was called for a personal foul by referee Hue Hollins, who determined that Pippen made contact with Davis. Television replays indicated that contact was made after Davis had released the ball. Davis successfully made both free throw attempts to assist in the Knicks victory, 87–86, and gave the Knicks a three games to two advantage in the series. The resulting incident was described as the most controversial moment of Hollins' career by Referee magazine. Hollins defended the call after the game saying, "I saw Scottie make contact with his shooting motion. I'm positive there was contact on the shot." Darell Garretson, the league's supervisor of officials and who also officiated in the league, agreed with Hollins and issued a statement, "The perception is that referees should put their whistles in their pockets in the last minutes. But it all comes down to what is sufficient contact. There's an old, old adage that refs don't make those calls in the last seconds. Obviously, you hope you don't make a call that will decide a game. But the call was within the context of how we had been calling them all game." Garretson later changed his stance of the call the next season. Speaking to a Chicago Tribune reporter, Garretson described Hollins' call as "terrible". Chicago head coach Phil Jackson, upset over the outcome of the game, was fined $10,000 for comparing the loss to the gold medal game controversy at the 1972 Summer Olympics.

In Game 6, Pippen made the signature play of his career. Midway in the third quarter, Pippen received the ball during a Bulls fast break, charging toward the basket. As center Patrick Ewing jumped up to defend the shot, Pippen fully extended the ball out, absorbing body contact and a foul from Ewing, and slammed the ball through the hoop with Ewing's hand in his face. Pippen landed several feet (some meters) away from the basket along the baseline, incidentally walking over a fallen Ewing. He then made taunting remarks to both Ewing and then Spike Lee, who was standing courtside supporting the Knicks, thus receiving a technical foul. This extended the Bulls' lead to 17; they won 93–79.

In the final Game 7, Pippen scored 20 points and grabbed 16 rebounds, but the Bulls still lost 87–77. The Knicks then proceeded to the NBA Finals, where they lost to the Houston Rockets, also in seven games.

With the return of Michael Jordan and the addition of multiple NBA rebound leader Dennis Rodman, the Bulls posted the best regular-season record in NBA history at the time (72–10) in 1995–96 en route to winning their fourth title against the Seattle SuperSonics. Later that year, Pippen became the first person to win an NBA championship and an Olympic gold medal in the same year twice, playing for Team USA at the Atlanta Olympics.

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. On February 23 Pippen was voted "Player of The Week" for the week of February 17, his 5th and final time to receive that honor. As the league entered its final weeks the Bulls lost several of their key players, including Bill Wennington (ruptured tendon in his foot), Dennis Rodman (injured knee), and Toni Kukoč (inflamed sole on his foot). Pippen and Jordan were forced to shoulder a greater load while keeping the team headed towards a playoff appearance. Even with this challenge Chicago finished a league-best 69–13 record. In the final game of the regular season, Pippen missed a game-winning 3-pointer, leaving the Bulls just short of having an NBA record-setting back-to-back 70-win seasons. For his efforts in the 1996–97 NBA season, Pippen earned NBA All-Defensive First Team honors for the 7th consecutive time as well as All-NBA Second Team honors.

Despite injuring his foot in the Eastern Conference Finals against the Miami Heat, Pippen helped the Bulls to an 84–82 victory over the Utah Jazz in Game 1 of the NBA Finals. One of the highlights of the game was when Jazz star Karl Malone was fouled by Dennis Rodman with 9.2 seconds left and had a chance to give Utah the lead and Pippen famously psyched Malone out, before he stepped up to the line, by saying: "Just remember, the mailman doesn't deliver on Sundays." He missed both free throws. Jordan got the rebound and quickly called a time-out with 7.5 seconds left. With play resumed, Jordan dribbled out most of the clock, then launched a 20-foot (6 m) shot that went in at the buzzer to give Chicago a 1–0 series lead. In Game 3 of the series, Pippen tied a then finals record of seven 3-pointers, but Chicago still lost 104–93. In Game 5 Jordan was battling illness but still managed to dominate the game, with the Bulls winning 90–88. 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". During Game 6, Pippen made one of the greatest plays of his career. Trailing by two, after Steve Kerr's jump shot with 5 seconds remaining, the Jazz looked for a final shot to stay alive, but Pippen knocked away Bryon Russell's inbound pass intended for Shandon Anderson and rolled the ball over to Toni Kukoč, who dunked to give the Bulls a 90–86 lead, clinching their fifth championship. Afterwards, Jordan was named Finals MVP for the fifth time.

On July 11, 2013, Camran Shafighi filed a $4 million lawsuit against Pippen in Los Angeles Superior Court over an incident that occurred on June 23, 2013, at the Malibu restaurant Nobu. Shafighi said that he was physically attacked by Pippen after taking pictures of Pippen inside and outside the restaurant. Shafighi was then taken to a hospital. On August 27, 2013, the Los Angeles County district attorney's office announced that charges would not be filed against Pippen.

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.

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."

Pippen is a two-time inductee into the Naismith Memorial Basketball Hall of Fame (for his individual career, and as a member of the "Dream Team"), having been inducted for both on August 13, 2010. On December 8, 2005, the Chicago Bulls retired his number #33, while his college, University of Central Arkansas, retired his number #33 on January 21, 2010, as well.

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.

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.

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."

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.

After the 2002–03 season, Pippen left Portland in order 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 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 would mark the first time in Pippen's career that his team did not reach the playoffs. Pippen was 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 419). On October 5, 2004, Pippen announced his retirement.

In the 2000–01 NBA season, Pippen played 64 games, starting in 60 of them. He was forced to miss 18 games, due to a tendinitis in the elbow of his right arm, which was his shooting arm. Pippen started being bothered by minor injuries during December but still managed to play. His right arm stiffened after a game with the Boston Celtics on January 8. He missed the next six games and, after a two-point performance in a loss to the Sacramento Kings on January 20, the injury became too painful for him again. He had the elbow examined by several doctors before going into surgery. After undergoing the 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. Pippen finished the season with averages of 11.3 points per game, 4.6 assists and 5.2 rebounds per game. The Trail Blazers finished the season with a 50–32 record, fourth in the Pacific Division and seventh in the Western Conference. They were swept in the first round of the playoffs, by the returning and eventual repeat champions, the Los Angeles Lakers.

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 under 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 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 Rocket's early elimination from the playoffs, Pippen expressed that he wanted 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 because 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.

Pippen claimed the starting small forward position with the Portland Trail Blazers in the 1999–2000 NBA season. Playing alongside new stars such as Rasheed Wallace and Steve Smith, Pippen continued to demonstrate his defensive capabilities, even past his prime. On January 3, when the Trail Blazers faced the Bulls, Pippen was honored with a video tribute highlighting his best moments in his 11-year career with the Bulls. Pippen later commented on the tribute by saying: "It was very emotional for me, but I tried to handle it as well as possible realizing I had a game to play. It was something that brought back a lot of memories for me, a lot of things I miss about this city, playing in this arena." Under Head coach Mike Dunleavy, the Trail Blazers posted a 59–23 record and clinched the second spot in the Pacific Division and the third spot in the Western Conference. Pippen played and started in all 82 games that season, averaging 12.5 points per game, 5 assists and 6.3 rebounds per game. In the first round of the 2000 NBA Playoffs, Portland defeated the Minnesota Timberwolves 3 games to 1. Their opponents in the second round were the Utah Jazz. In Game 5, while leading the series 3–1 and Portland trailing by 2, Pippen hit a three pointer with 7.3 seconds remaining. The Jazz fouled Pippen on the next play, and he made one of two free throws to give the Blazers an 81–79 lead. The Trail Blazers won the series 4–1 and advanced to the Western Conference Finals. There, they faced the Los Angeles Lakers, coached under Phil Jackson, Pippen's former coach in Chicago. The series was stretched to a deciding Game 7, in which the Trail Blazers held a 15-point lead in the 4th quarter. 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. The Lakers proceeded to the 2000 NBA Finals where they faced the Indiana Pacers and were eventually crowned the NBA Champions.

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.

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

The 1997–98 season began amid speculation that it would be the last in Chicago for Pippen, Jordan, and Jackson. Pippen had purposefully delayed off-season surgery so that his summer off-season would not be complicated by rehab, pushing his unavailability well into the regular season. In addition to this increasing the load on Jordan to drive the team towards a potential final championship together, it stirred an active effort by Bulls general manager Jerry Krause to trade Pippen, who responded in turn with his own trade demand and rancorous sit-out that extended well beyond his return to playing condition. In spite of this Pippen ultimately rejoined the team, without any much-deserved contract renegotiation to pay him what he was worth relative to the then league pay scale, and joined Jordan in another Bulls run to the 1998 NBA Finals, where they again bested the Jazz to win their second three-peat.

Considered one of the greatest small forwards of all time, Pippen was named to the NBA All-Defensive First Team eight consecutive times and the All-NBA First Team three times. He was a seven-time NBA All-Star and was the NBA All-Star Game MVP in 1994. He was named one of the 50 Greatest Players in NBA History during the 1996–97 season, and is one of four players to have his jersey retired by the Chicago Bulls (the others being Jerry Sloan, Bob Love, and Michael Jordan). He played a main role on both the 1992 Chicago Bulls Championship team and the 1996 Chicago Bulls Championship team which were selected as two of the Top 10 Teams in NBA History. His biography on the Naismith Basketball Hall of Fame's website states, "The multidimensional Pippen ran the court like a point guard, attacked the boards like a power forward, and swished the nets like a shooting guard." During his 17-year career, he played 12 seasons with the Bulls, one with the Houston Rockets and four with the Portland Trail Blazers, making the postseason sixteen straight times.

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.

Trade rumors involving Pippen escalated during the 1994 off-season. Jerry Krause, the Bulls' general manager, was reportedly looking to ship Pippen off to the Seattle SuperSonics in exchange for all-star forward Shawn Kemp, moving Toni Kukoč into Pippen's position as starting small forward with Kemp filling in the vacant starting power forward position in place of Horace Grant, a free agent who left the Bulls for the up-and-coming Orlando Magic during the off-season. In January, when asked by the late Craig Sager as to whether he thought that he would be traded, Pippen replied, "I hope I am". However, Pippen would remain a Bull and those rumors were put to rest once it was announced that Michael Jordan would be returning to the Bulls, late in the 1994–95 season. Badly lacking interior defense and rebounding due to Grant's departure, the Pippen-led Bulls did not play as well in the 1994–95 season as they had in the season before. In fact, for the first time in years, they were in danger of missing the playoffs. The Bulls were just 34–31, prior to Jordan's return for the final 17 games, and Jordan led them to a 13–4 record to close the regular season. Still, Pippen finished the 1994–95 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), and Giannis Antetokounmpo (2016–17) have since matched it.

Pippen was famed for his defensive abilities, having made the NBA All Defensive Team ten consecutive years during his career and leading the league in steals in 1994–95. Jackson once described him as a "one-man wrecking crew", capable of guarding anyone from the point guard to the center position. Pippen is one of three players in NBA history (along with Jordan and Olajuwon) to record 200 steals and 100 blocks in a season, and he has the record for second most career steals in the playoffs (395) behind James. He was skilled at staying in front of his man on defense, and particularly effective as a help defender, with his long arms in traps. He was also capable of chasing down an opposing player in transition to block shots from behind.

Michael Jordan retired before the 1993–94 season and in his absence Pippen emerged from Jordan's shadow. That year, he earned All-Star Game MVP honors and led the Bulls in scoring, assists, and blocks, and was second in the NBA in steals per game, averaging 22.0 points, 8.7 rebounds, 5.6 assists, 2.9 steals, and 0.8 blocks per game, while shooting 49.1% from the field and a career-best 32% from the 3-point line. For his efforts, he earned the first of three straight All-NBA First Team selections, and he finished third in MVP voting. 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 is the only NBA player to have won an NBA title and Olympic gold medal in the same year twice (1992, 1996). He was a part of the 1992 U.S. Olympic "Dream Team" which beat its opponents by an average of 44 points. Pippen was also a key figure in the 1996 Olympic team, alongside former Dream Team members Karl Malone, John Stockton, Charles Barkley and David Robinson as well as newer faces such as Anfernee "Penny" Hardaway and Grant Hill. He wore number 8 during both years.

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.

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 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.

His intense work ethic and athletic physique gave him the ability to consistently make highlight-reel plays, such as applying defensive intensity, forcing a turnover, stealing the ball and starting a one-man fast break that he would finish with a thunderous slam dunk. As Pippen himself has attested, he and Jordan would compete to see who could force more turnovers and produce more offense from defense in each game (fast break points). During the 1990 Slam Dunk Contest, Pippen exhibited his leaping ability with a dunk from the free throw line. He was an athletic finisher at the rim, both with dunks and a skillful finger roll that he added to his skill set over time. He was also a prolific perimeter shooter for the time, taking about 3,000 and making almost 1,000 three-pointers in his career.

His unusually long arms (2.2 m (88 in) wingspan) and jumping agility helped him to clog the passing lanes on defense, to block shots from behind on players that had managed to pass him by, to grab seemingly out-of-reach rebounds, to make unusual plays in mid-air, and to make passes around defenders that most players are physically unable to make. He often led the Bulls in assists and blocks as a result. Pippen was also a selfless player. His team-focused approach to the game was a key component in the Bulls' championships. Pippen's career assists total of 6,135 (5.2 per game) is a testament to that approach. It was 23rd all-time among all players when he retired.

Pippen has been married twice: to Karen McCollum (married 1988; divorced 1990) with whom he has a son, Antron Pippen (born 1987), and to Larsa Younan (married 1997; divorced 2018), with whom he has four children: Scotty Jr. (born 2000), Preston (born 2002), Justin (born 2005), and Sophia Pippen (born 2008). Larsa starred in the TV show The Real Housewives of Miami, and is of Assyrian heritage. Scotty Jr. is a freshman on the basketball team at Southeastern Conference (SEC) Vanderbilt University. Sophia appeared on the first season of Dancing with the Stars: Juniors. Pippen also has a daughter, Sierra Pippen (born 1995), with his former fiancée Yvette De Leon and a daughter, Taylor Pippen (born 1994), with former girlfriend and model Sonya Roby. Taylor's twin sister Tyler died nine days after birth. Taylor played volleyball at Southern Illinois University. Taylor is an accountant in Chicago.

Pippen attended Hamburg High School. Playing point guard, he led his team to the state playoffs and earned all-conference honors as a senior. He was not offered any college scholarships. Pippen began his college playing career at the University of Central Arkansas in Conway after being discovered by the school's head basketball coach, Don Dyer, as a walk-on. He did not receive much media coverage as a college basketball player because Central Arkansas played in the NAIA, not the more prestigious NCAA. Pippen stood only 6 ft 1 in (1.85 m) tall when he graduated from high school, but while at Central Arkansas experienced a growth spurt 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 but selected too low, 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.

Scotty Maurice Pippen (born September 25, 1965), commonly spelled Scottie Pippen, is an American former professional basketball player. He played 17 seasons in the National Basketball Association (NBA), winning six NBA championships with the Chicago Bulls. Pippen, along with Michael Jordan, played an important role in transforming the Bulls into a championship team and in popularizing the NBA around the world during the 1990s.

Pippen was born on September 25, 1965, in Hamburg, Arkansas, the youngest of 12 children, born to Ethel and Preston Pippen (June 9, 1920 – May 10, 1990). Pippen's 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 Scottie being the tallest. His parents could not afford to send their other children to college. His father worked in a paper mill until a stroke, that paralyzed his right side, prevented him from walking and affected his speech.