i'm with you on this one, i have them in two tiers:
Tier 1
Bill Russel - not only did he just win, but his legacy of combating racism transcends his on the court accomplishments
Ted - gave up 5 seasons in his prime, ended up being one of the greatest fighter pilots of his era (john glenn called him the best), and then just picked up where he left off......greatest hitter of all time
Tier 2
Orr - redefined the position, changed the game......his knees betrayed him, but he ushered in the modern era of hockey
Tom Brady - GOAT QB, just a winner, he is the poster boy for making the most of opportunity and getting it done when it counts
i think the real debate happens with 5, 6,7 & 8