Eddie Cicotte was known to be an inconsistent player when he was with the Boston Red Sox, and he would run afoul of Red Sox management who sold him to Chicago during the 1912 Season. 

In terms of iconic figures, would have been wrong if we placed Minnie Minoso at number one?  Clearly, we didn't, but the native of Havana, Cuba, will always be one of the most revered athletes in the history of Chicago.

The offensive leader of the Chicago’s “Go-Go Sox” teams of the 50s, Nellie Fox first arrived in the Windy City when he was traded after the 1949 season straight up for Joe Tipton.  This transaction would turn out to be one of the most lopsided trades in history, as Tipton would only have 113 Hits for the Athletics, and Fox would begin his march to Cooperstown.