Boston
Baseball - David Ortiz - For doing it in October over maybe the greatest overall hitter ever in Ted Williams
Basketball - Bill Russell - Over Larry Bird for being the greatest leader/winner in sports
Hockey - Bobby Orr - Light years ahead of his time in his sport. Light years ahead of his time as anyone in any sport
Football - Tom Brady - Consistent winner, maximized his abilities, never satisfied, the next championship is as important as the last