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Winning their first championship in what was the beginning of a dynasty. Scottie Pippen would be an all-star the next six straight years. He went on to make a total of 10 all defense team selections. Lead the leaves in steals for a season and won his famous 6 championship rings. During his time as a Chicago Bull, Scottie was always a supporter to Michael Jordan's Batman, except for one small sample size of a season and a half, this sample should weigh heavily on how we define Scottie Pippen's legacy.

At the end of the Bulls first three-peat in the 1993 season. Jordan announced his retirement from basketball in order to pursue his love for baseball. In Jordan's absence Pippen emerge from a 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 points, 8.7 rebounds, 5.6 assists, 2.9 steals and 0.8 blocks per game, while shooting 49.1% from the field. For his efforts he earned the first of three straight All-NBA first team selections and he finished third in the MVP voting.

The Bulls had made key additions that seasons of Toni Kukoc, Steve Kerr and Luc Longley and had finished the Jordan leaves season with 55 wins, good enough for the third best record in the Eastern Conference. Pippen had taken the reigns as leader of the defending championship Chicago Bulls, and he wasn't just doing a good job but an excellent one.

The Bulls comfortably swept the Cavaliers in the first round of the playoffs and that set them up with a matchup with their physical rivals the New York Knicks. Pippen continued to lead the Bulls through the series and although Pippen produced quality averages of 22 points, 8 rebounds and 5 assists. The Knicks physical defense was clearly affecting his efficiency as he shot only 40% from the field that series.

The two teams battled hard deep into the series and in the sixth game. Pippen made the most iconic moment of his career. Midway through the third quarter, Pippen was on a fast-break charging towards the basket as Center Patrick Ewing jumped up to defend him. Pippen utterly posterized Ewing, absorbing contact and a foul and slam the ball through the hoop. Pippen proceeded to walk over the destroyed Ewing. He then taunted both Ewing and iconic Knicks fans Spike Lee who was standing courtside. Pippen received a technical foul for the taunting, but it was worth the moment. That has since been immortalized in the great moments of playoff history. The Bulls handily won the game pushing the series to seventh game. In the seventh game, Pippen scored 20 points and added a monstrous 16 rebounds, but ultimately didn't receive enough help and the Bulls were eliminated 87 to 77.