Four: Bill McKechnie (1925 Pittsburgh Pirates, 1940 Cincinnati Reds); Bucky Harris (1924 Washington Senators, 1947 New York Yankees); Sparky Anderson (1975 and 1976 Cincinnati Reds, 1984 Detroit Tigers); and Tony LaRussa (1989 Oakland A's, 2006 St. Louis Cardinals). Both Anderson and LaRussa won World Series in the National League and the American League.
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The first to accomplish the feat was George "Sparky" Anderson, who won two world championships with the Cincinnati Reds (1975-76) and a third with the Detroit Tigers (1984). The only other person to do it was Tony La Russa, who won the 1989 World Series with the Oakland A's and two world championships with the St. Louis Cardinals (2006, 2011).
1) Sparky Anderson - 1975 and 1976 Cincinnati Reds, 1984 Detroit Tigers
2) Tony LaRussa - 1989 Oakland Athletics, 2006 St. Louis Cardinals