Chicago Bulls (1987–1998)
Having eyed Pippen before the 1987 NBA draft, the Chicago Bulls manufactured a trade with the Seattle SuperSonics that sent Pippen, selected fifth overall, to the Bulls in exchange for the eighth pick, 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 during their rookie seasons. Pippen made his NBA debut on November 7, 1987, when the Chicago Bulls opened against the Philadelphia 76ers. He finished with 10 points, two steals, four assists, and one 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 finishing third in the league in steals with 211 during the 1989–1990 season. 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. In each season, the Bulls were eliminated by the Detroit Pistons. 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.
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 Jordan, Pippen continued to improve his game, especially in shooting from the field. 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 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 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 steals and steals per game. For his efforts in the 1990–91 NBA season Pippen was awarded NBA All-Defensive Second Team honors. The Bulls went on sweep the two-time defending champions Detroit Pistons in the Eastern Conference Finals, then defeated the Los Angeles Lakers in the 1991 NBA Finals with Pippen defending effectively against Lakers superstar Magic Johnson.
Pippen helped lead the Bulls to their first three-peat, as they won the following two years in 1992 and 1993.
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.
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.
A key play occurred in 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 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 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.
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 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 season as they had in the season before. 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 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.
With the return of Michael Jordan and the addition of multiple-time NBA rebound leader Dennis Rodman, the Bulls posted the best regular-season record in NBA history at the time (72–10) in 1995–96 (later surpassed in 2015–16 by the Golden State Warriors) 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.
The Bulls opened the 1996–97 NBA season with a 17–1 record and had a league-best record of 42–6 when entering the All-Star break. In November 1996, Pippen set the NBA single-month plus-minus record of 272. Both Pippen and Jordan were selected among the 50 Greatest Players in NBA History 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.
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 fifth 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 seventh 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, which was decided by Jordan's game-winning buzzer beating jumper. 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.
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 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.
