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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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.
Connie Mack managed in 7,755 games from 1894-1950. He also holds the record for most games won and most games lost.
Connie Mack managed the Pittsburgh Pirates between 1894-1896 and the Philadelphia Athletics between 1901-1950. His record was 3731-3948.
The New York Yankes won 26 World Series titles in 39 appearances.
The New York Yankees appeared in six World Series during that period: in 1998, 1999, 2000, 2001, 2003 and 2009.
Through the 2010 season, that is the Houston Astros with 9 playoff appearances without a World Series win.
With 14 World Series appearances, Yankees catcher and outfielder Yogi Berra played the most times in this event. Berra, who played 19 major league seasons for the Yankees, appeared in the Fall Classics of 1947, 1949-1953, 1955-1958 and 1960-1963. The Yankees won 10 world championships during that time.
Joe McCarthy won the most games as Yankees manager with 1,460. Both Joe McCarthy and Casey Stengel have won the most World Series championships with seven.