Frank Chance was the player/manager of the Cubs that defeated the Tigers in both the 1907 and 1908 World Series ... he also played first base.
Chance was player/manager of the Cubs between 1905-1912 and also led the team to the 1906 and 1912 World Series that they lost (1906 to the White Sox and 1912 to the Red Sox). He was inducted into the Hall of Fame in 1946.
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the last time the Chicago Cubs won the world series was 1908 having the longest losing streak of 96 years
Frank Chance.
Chance was the player/manager of the Cubs for the two World Series they have won (1907 and 1908). He played first base along with managing the team.
That was Don Baylor whose first year managing the Cubs was 2000 and was fired after 83 games of the 2002 season. Baylor's record with the Cubs was 187-220.