1. Kobe Bryant, Shooting Guard
The final name on this list did all of his damage against Pippen after his initial run with the Bulls was over. The second run with the Bulls didn’t get Pippen far enough in the playoffs either to even have a shot at facing the former Lakers superstar shooting guard Kobe Bryant in the NBA Finals.
Kobe and Shaq together gave Pippen a lot of fits in the playoffs when they played together in LA. Pippen was never able to get that far in the playoffs out West when his former head coach Phil Jackson was running things with the Lakers. The Lakers and the San Antonio Spurs were the new emerging powers in the NBA at the time.
And a big reason for the Lakers rise to power in the West was Kobe. He was an 18-time NBA All-Star selection, five-time NBA Champion, two-time scoring champ, and 12-time All-Defensive Team selection. Kobe got to face Pippen 21 times in the regular season and 17 times in the playoffs. Both of which Kobe actually held the series edge against Pippen.
Kobe held a dominant record of 13-4 in the playoffs against Pippen, and 13-8 in the regular season. He averaged 21.7 points per game, 5.5 rebounds, 6.0 assists, 1.9 steals, and 1.6 blocks. Kobe shot 42.0 percent from the field, 43.6 percent from beyond the arc, and 78.6 percent from the free-throw line in those 17 playoff games against Pippen.
Meanwhile, Pippen averaged 15.8 points per game, 9.1 rebounds, 4.2 assists, 2.2 steals, and 0.8 blocks. Considering Pippen mostly faced Kobe in the playoffs when he was playing out West, that was a pretty solid stat line for him.