Pippen always had a lot of confidence in his game and welcomed the challenge of playing alongside Jordan, who won his first MVP Award during Pippen’s first season with the Bulls in 1987-88. Chicago, though, struggled to get past the Detroit Pistons in the Eastern Conference playoffs and needed another superstar next to Jordan.
Many pundits thought the Bulls would need to trade for Jordan’s sidekick. However, MJ knew Pippen was destined for superstardom before anyone else.
Michael Jordan knew Scottie Pippen would turn into a superstar in 1989-90
Pippen made his first All-Star team during the 1989-90 season. Before the campaign started, Jordan told a room filled with Bulls fans that Pippen was destined for superstardom after a kid asked him about the talented swingman.
“Scottie is a late bloomer, as we call it in the NBA,” Jordan said. “He doesn’t really start to perform his athletic skills until later in his years. He’s always been kind of overshadowed by not going to a Division I school, but he has a lot of ability, and he’s starting to come into his own right now.”
Pippen averaged 16.5 points, 6.7 rebounds, and 5.4 assists in 1989-90, the first season Phil Jackson coached the Bulls and installed the triangle offense. Jordan finally had a partner in crime, and many NBA analysts believe Chicago could have defeated the Pistons in Game 7 of the 1990 Eastern Conference Finals had Pippen not dealt with a migraine.
Jordan and the Bulls were heartbroken after losing to the Pistons for the third consecutive postseason. Instead of whining, though, they bulked up in the summer of 1990 and were a totally different team in 1990-91.
Michael Jordan and Scottie Pippen swept the Pistons in ’91
Behind Jordan and Pippen, the Bulls won 61 games in 1990-91. MJ averaged 31.5 points and won his second MVP, while Pippen put up 17.8 points, 7.3 rebounds, and 6.2 assists per game.
The Bulls faced the Pistons in the 1991 Eastern Conference Finals and eliminated them in four quick games. They finally got past their biggest rivals and were excited about advancing to their first NBA Finals. Even though the Pistons’ walk-off stole all the headlines, Jordan and Pippen were ecstatic about sweeping Isiah Thomas and Co.
In the four-game sweep, Jordan averaged 29.8 points while shooting 53.5% from the field. Meanwhile, Pippen finished with averages of 22.0 points and 7.8 rebounds. He almost got seriously injured in Game 4 after Dennis Rodman pushed him into the crowd, but he showed his mental and physical toughness by not responding to the foul and getting up.
After getting past the Pistons, the Bulls met the Los Angeles Lakers in the ’91 Finals. What happened over the next eight years is something no one thought was possible.
The Bulls won six rings in eight years
The Bulls won an incredible six championships in an eight-year span during the ’90s. They could have won eight straight titles had Jordan not retired after the 1992-93 season.
Chicago, led by Jordan, Pippen, and Jackson, defeated the Lakers, Portland Trail Blazers, and Phoenix Suns during the first three-peat. After losing in the second round of the ’94 playoffs to the New York Knicks sans Jordan and falling to the Orlando Magic in the ’95 conference semifinals after MJ came back from his baseball stint, the Bulls won three more championships against the Seattle SuperSonics and Utah Jazz (twice).
Jordan and Pippen are the two best players in Bulls franchise history. They both have their numbers hanging in the rafters at the United Center and will be revered in Chicago forever.