Chicago Cubs: It took until 1971 for a Cub to win a Cy Young Award
The first man to win a Cy Young Award and wear a Cubs uniform was the Hall of Famer from Chatham Canada, Fergie Jenkins. This happened in 1971 when Jenkins was 28 years old and in his sixth season as a Cub.
Jenkins in 1971 pitched to a 2.77 ERA, 2.28 FIP, 1.05 WHIP, 263 strikeouts and 37 walks. He was first in the National League in innings pitched (325), wins (24) and starts (39). His 30 complete games were the most in all of baseball, and 1.0 BB/9 was best in baseball among qualifiers.
While fWAR is not always the best measure of pitchers, it is worth noting he posted a 9.6 fWAR that year, which was also best in baseball. He was seventh in MVP voting, but one could argue he was deserving of having more consideration for the award.
Jenkins was ninth in ERA and third in FIP in the National League. Those are two stats that Tom Seaver led the league in, but at the time, the win-loss record stood out. Looking back now, one could justify Jenkins winning the award by looking at how many more innings he pitched than Seaver (39 1/3) and had 24 also fewer walks than him. Jenkins had unbelievably great control and was able to complete 77% of his 39 starts, which is unheard of today.