Leo Durocher is the only manager in history to win 500 games with three different clubs. Though remembered mostly for his aggressive nature and constant spats with umpires, Leo the Lip was one of the most successful skippers in history. His managerial career can be divided into three parts: eight years with the Dodgers, eight with the Giants, and seven with the Cubs.
The former starting shortstop player-managed in Brooklyn, where he won 738 games overall and a pennant in 1941. In the spring of 1947 he temporarily defied his bad-boy reputation by crushing a players revolt against Jackie Robinson, but quickly made up for it by associating with mobsters and getting suspended for the year. Midway through 1948 he was fired by nemesis Branch Rickey, but replaced Mel Ott at the helm of the cross-town rival Giants. He brought two pennants to the Polo Grounds, including the 1951 title that culminated in the “Shot Heard Round the World.” Three years later he won 97 games and his only championship. He retired temporarily in 1955 with a 637-523 record in New York. He had a moderately successful return in 1966 with the Chicago Cubs, notching 535 victories but no playoff appearances.