Who do you guys think in order are the best boston sports legends ever? I'm talking just the players, not owners or coaches. For me it's: 1. edit: Ted Williams 2. Bobby Orr - arguably the greatest NHL player ever. 3. Tom Brady - arguably the greatest QB ever. 4. Larry Bird 5. Bill Russell - 11 NBA titles. The reason I put Orr number 2 is because he's possibly the greatest player of his sport ever. Bird and Russell are not the greatest NBA players and Brady might be one day.