#1 Scottie Pippen
Pippen is lauded as an all-time great defender, but often gets overlooked as he was playing next to Michael Jordan. Jordan won DPOY in 1988, but Pippen was never able to win the award.
For those who didn't watch NBA in the 90s, Pippen is comparable to Kawhi Leonard right now, and he showed even more intensity as the hand-check rules allowed him to make some contact without being called for a foul.
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Pippen received DPOY votes in nine seasons, finished in the top three on four occasions, and finished as high as second twice, but ultimately never won the award. 1995 is seen as the year he could have won it as the Bulls found success with him as their best player rather than Jordan.
With an increased offensive load in Jordan's absence, Pippen became one of the league's best offensive players, but he never let his defense tremble as a result. Most elite offensive perimeter players use defense to catch their breath so they can make another play with the ball, but Pippen worked hard on every single possession regardless of his offensive workload. In 1994-95 Pippen averaged 2.9 steals and 1.1 blocks per game, but ultimately fell short to Dikembe Mutombo who averaged 3.9 blocks per game to clinch the award.
He could smother the ball, played elite denial defense and made his man work hard just to get the ball, defended tough in the post, and was a mismatch nightmare due to his combination of strength, length and speed. Pippen was probably the best perimeter defender of the 90's, and for him to have zero DPOY awards seems like an error in the NBA history books.
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