Greg Maddux is always thought of first as an Atlanta Brave, but it was with the Chicago Cubs where he first rose to prominence.  Maddux started slowly with Chicago, but the talent was there, and in 1988, his third year in the Majors, he was chosen for the All-Star Game with an 18 Win season.  He was solid for the next three seasons, winning 19, 15, and 15 Wins, and in 1992, he would lead the NL with 20 Wins and had an ERA of 2.18.  He would win the National League Cy Young Award that year, would go to his second All-Star Game, and he had won his third straight Gold Glove.  Sadly, for the fans at Wrigley, Maddux was a Free Agent, and talks broke down, and he signed with Atlanta winning the next three Cy Youngs.  Maddux would, however, return later for two more seasons in 2004.

Carlos Zambrano played all of but his final season with the Chicago Cubs, where the Venezuelan was a three-time All-Star who also finished third in Cy Young voting five times.  In the first decade of the 2000s, Zambrano was one of the more dependable hurlers and was the only one in the NL who had at least 13 Wins from 2003 to 2008.  In 2006 he made history as the first Venezuelan to lead the National League in Wins, and he would finish in the top ten in ERA four times.

Hack Wilson was playing for Toledo of the American Association after falling into a slump with the New York Giants.  He was left unprotected (some say an oversight), and the Chicago Cubs swooped in and claimed him late in 1925.  The Giants loss was the Cubs game as Hack Wilson would win the National League Home Run crown in 1926, a feat he would repeat in 1927, 1928, and 1930.  Wilson wasn't just hitting for power as with the exception of 1931, and he never had a season where he batted under .300 or had an OBP under .400.  Wilson would twice lead the NL in Walks, and his Slash Line as a Chicago Cub is an incredible .322/.412/.590.

Playing for the Chicago White Stockings/Colts for seven seasons, Bill Hutchinson was a dominating presence for three of them, so much so that he earned this high ranking.  In each of those years (1890-92), Hutchinson would lead the National League in Wins and Innings Pitched, and he would also win the Strikeout Title in 1892 while finishing second in the other two seasons mentioned above.  After that, Hutchinson was an average Pitcher at best, playing three more seasons without doing anything special, but after it was said and done, his career at Chicago would see him win 180 Games with 1,225 Strikeouts.