Re: Isiah Thomas/Bill Russell or Walt Frazier/Kareem
In a 2v2, I would have to go with Kareem/Frazier. Russell's skills and intangibles lend themselves perfectly to 5 on 5 but not so much for a 1v1 or 2v2. Kareem would probably be too much to handle.
And the exact same can be said for Isiah. He would find it hard being guarded by an all time great defender in Frazier.
In a regular 5 on 5, I'm taking Russell and Isiah. They are both born leaders. They are both insanely competitive. They both make everyone around them better. They are both clutch (yes, Kareem and Frazier are clutch, but i think they are just a notch behind Russell and Isiah).
Their styles would compliment each other nicely. Russell would defend and rebound. Isiah would pass and score. Surround them with the right players and they would be tough to beat.