Short Answer: White Sox
The Chicago White Sox won three World Series ... 1906, 1917, and 2005, while the Chicago Cubs have only won two ... 1907 and 1908.
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The Chicago White Sox have won three World Series -- in 1906, 1917, and 2005. The Chicago Cubs won in 1907 and 1908.
Yankees
Yankees 26
Yankees 26! Go yanks all the way :)
Chicago cubs. Have not won since 1908
Yogi Berra appeared in 14 World Series as a player for the Yankees and won 10 championships. Yogi also won 2 World Series championships as a Yankees coach in 1977 and 1978.