Scottie Pippen
(Kalb: #29, Simmons: #24, BBR: #22)
Scottie Pippen is one of the more interesting cases on this list. He spent most of his career as the second-best player on his team, but he won a lot of championships and was actually a much better player than most people realize.
When I profiled David Robinson a few spots ago, I mentioned that he was the committee's #4 choice to be on the Dream Team in 1992, behind only Magic, Michael, and Bird. Do you happen to know who their #5 choice was? Scottie Pippen. After picking the best four guys who were franchise players and well-respected superstars, they picked Scottie Pippen, who wasn't even the best player on his own team. That's because they saw that the Bulls were more than just Michael Jordan.
In 1992, just before that team was selected, Pippen put together a season that very few have ever come close to. His averages for that year were 21 points, 7.7 rebounds, 7.0 assists, 1.9 steals, and 51% shooting from the field. For reference, only 8 other players have ever averaged a 21-7-7, and only 5 others have done it while shooting over 50%. Those five? Bird, Wilt, Magic, Michael, and Oscar. Not bad company, especially considering each of those players has yet to make an appearance in these rankings.
Jordan and Pippen played together for 10 season, and in each of those ten seasons they made the playoffs and advanced beyond the first round together. Jordan played 5 seasons without Pippen, three before he arrived and two after they separated in 1998. In those 5 seasons his teams made 3 playoff appearances and never advanced past the first round. Pippen, meanwhile, played 7 seasons without Jordan, making the playoffs 6 times and advancing past the first round twice. I'm not suggesting that Pippen was better than Jordan, but it's significant that Jordan needed Pippen in order to be successful.
Scottie Pippen was also recognized as being one of the best defensive small forwards of all time, as evidenced by the 8 straight seasons during the 1990's that he was named to the All-Defensive First Team. He led the league in steals in 1995, and finished in the top 5 three other times. Pippen was the player that the Bulls used to guard the other team's best player at four positions, and it was a tipped pass and steal by Pippen that sealed the 1997 Finals victory over Utah after Steve Kerr hit his famous series-winning shot.
Another thing Pippen has going for him is that he is one of a select group of players who has too many championship rings to fit on one hand. He was the second-best player on 6 championship games in 8 seasons, and was also the second-best player on a Portland team in 2000 that came within one game of the NBA Finals.
Pippen never quite reached the career heights that Garnett did, but that is because Pippen recognized that he had an important role to play to help his team win championships, and that didn't always involve him being the man. Pippen only missed the playoffs once in his career, in his final season when he was riding the bench in Chicago as a 38-year-old. Both Pippen and Garnett were great all-around players, filling up every part of the stat sheet, but Pippen gains the edge over Garnett because of the 12 season in which he advanced past the first round of the playoffs, with 6 championships as the result, while Garnett has only passed the first round 3 times with one title.