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Charlie Grimm, who managed the Cubs between 1932-1938, 1944-1949, and 1960, is the all time winningest manager in Cubs history. His all time record with the Cubs was 946-782 and he led the team to the World Series in 1932, 1935, 1938, and 1945.

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17y ago

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That is Casey Stengel of the New York Yankees who managed the team to 10 World Series: 1949, 1950, 1951, 1952, 1953, 1955, 1956, 1957, 1958, 1960 The Yankees won seven World Series and lost three under Stengel.

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16y ago
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  1. Sparky Anderson 1970-78 with the Reds, 1979-95 with the Tigers...
  2. Manny Mota has been listed as a coach for the Dodgers since 1980, making the 2010 season the 31st consecutive year in which Mota has coached for the team...
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14y ago
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Connie Mack managed in 7,755 games from 1894-1950. He also holds the record for most games won and most games lost.

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21y ago
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Connie Mack managed the Pittsburgh Pirates between 1894-1896 and the Philadelphia Athletics between 1901-1950. His record was 3731-3948.

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17y ago
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Connie Mack is first with 3,731 games won and John McGraw is second with 2,763.

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15y ago
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Q: What manager has the most World Series appearances?
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