Minstrel

Pippen was in the twilight of his career then. And was still immensely valuable to the Blazers, despite being much diminished from his prime level.

Pippen proved that he was very capable of being the franchise player in the year Jordan went to play baseball. That's the chance to see what Pippen could do in his prime as the main star. He took a team with no prior All-Stars (Armstrong and Grant made the All-Star team for the first time that year) to within a bad referee call of the Eastern Conference Finals.

So, I don't see any reason to believe that Pippen-led teams couldn't have achieved what Drexler-led teams did. Drexler had plenty of talent surrounding him in Portland's successful teams of that era. Pippen surrounded by as much talent would likely also have done extremely well.

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You'll never live like common people
You'll never do what common people do
You'll never fail like common people
You'll never watch your life slide out of view
And dance and drink and screw
Because there's nothing else to do.