While Kiki Cuyler’s best years in baseball were as a Pittsburgh Pirate, he actually spent more time with the Chicago Cubs.  Playing 949 Games for Cubs, Cuyler would have five seasons where he batted over .300, two of which would see him exceed .350.  Cuyler's first three years in Chicago (1928-30) would see him lead the National League in Stolen Bases, and he would also finish first in Doubles in 1934.  Overall, he batted .325 with 1,199 Hits for the Cubs, and he would be chosen for the Baseball Hall of Fame in 1968 when he was voted in by the Veteran's Committee.  The Cubs would also place Cuyler into their Hall of Fame in 2021, the first year of their exstence.

Heinie Zimmerman was a member of the Chicago Cubs World Series Champions in 1907 and 1908, but this was early in his career, and he didn't play much for the Cubs at the time. Instead, he would come into his own in the early 1910s, and in 1912 specifically, he would win the Triple Crown with a stellar .372 Batting Average.  Zimmerman would also lead the National League in Hits (207), Doubles (41), and Slugging Percentage (.571) but amazingly only finished sixth in MVP voting.  Zimmerman would have two other .300 seasons, and overall as a Cub, he would bat .304 with 1,112 Hits.  Had he a better On Base Percentage (.343), he would probably be a few spots higher on this list.

Zimmerman entered the Cubs Hall of Fame as part of the first class in 2021.

The story of Andre Dawson has long been told when it comes in relation to the Chicago Cubs.  It was the year of "Collusion," and Dawson and his agent agreed to a blank amount in front of the Cubs management.  The Cubs would sign him for a half a million dollars, a bargain in every stretch of the word.  "The Hawk" would then proceed to have the best season of his career where he blasted a league-leading 49 Home Runs, and 137 Runs Batted In and would win the National League MVP Award.  Dawson never had a year like that again, but he was still a good power hitter who would have 20 or more taters in the next five seasons.

While we stated that Anthony Rizzo was the heart of the Cubs' 2016 World Series Championship, Kris Bryant was the star.