3. Bill Carrigan 1913-1916; '27-29 1,003 games Finished *4th, 2d, 1st, 1st, 8th, 8th, 8th With back-to-back World Series titles (when he nurtured The Babe), Carrigan's ranking might have been higher but for his horrible comeback in the late '20s when he managed some of the worst teams in Sox history.