Don’t know how I missed this topic over the last 3-4 months, but here’s my late take:
A bunch of people have said, “depends who your #1 is”? But that usually seems to go “is your #1 a low post or perimeter player?” So besides that argument, I think you also have to consider who your #1 personality wise.
Wade, I could see playing second fiddle to just about anybody, regardless of position
Pippen, I could only see playing second fiddle only to a select few, dominant personalities like Jordan, Bird.
Pippen teamed with Barkley and Hakeem in Houston, arguably still in his prime (1st team All-Defensive), yet that didn’t work at all, and I remember Pippen openly complaining about the situation and not being happy with his role (although you could argue he had a problem being the 3rd fiddle).
Pippen was on a very stacked Portland team that choked. No clear cut leader on that team.
The infamous “Kukoc play” where he refused to re-enter the game because the play wasn’t called for him.
The migraine game.
Forget the position of my #1, I think Pippen also needs a hard-nosed, no-nonsense #1, that is clearly better than him. A Jordan or Bird type guy. Could Durant or Amare or Duncan or even Shaq get the most out of Pippen? I have some doubts if he would be as good/great. Would Pippen work as well in a Miami or Boston situation where he would be one of 3 “leaders” without a clear cut first and second fiddle situation? I have my doubts. But Wade I could see working in just about any situation, even if the #1 plays the same or similar position.