1. Red Auerbach
Record and Accolades: 823-426 (.629 winning percentage), 9 NBA Championships (8 won consecutively), 1965 Coach of the Year
Red Auerbach was simply the definition of a winner. His teams didn't just pick up Ws, they dominated. Red led nine of his teams to championships in 20 seasons as coach of the Boston Celtics. The coaching legend also helped break color barriers during a time when the NBA was predominantly white. Auerbach drafted the league's first black player, Chuck Cooper, in 1950 and his 1964 team was made up of the first all-black starting five. On top of that, Red did it all with his own bit of swag, most notably his habit of celebrating with victory cigars. No Lewinsky.