Qualifiers: players will be classified under one position even if they played at more than one. They must also have at least two seasons as the team's primary starter at the position. Ernie Banks spent significant time at multiple positions and will appear at shortstop where he played his best years.
Cap Anson:
One of Major League Baseball's early greats, Hall of Famer Cap Anson played more than two decades with the Chicago Cubs dating back to their inaugural National League season as the Chicago White Stockings. Anson ranked among the top ten batting leaders 16 times in 22 seasons including two batting title wins. His lifetime .334 average carried him to 3,435 hits, the sixth most in baseball history. He was the first professional ball player to reach the 3,000 hit milestone and he reached base more than 4,400 times in his career. His 89.1 WAR (wins above replacement) is the highest by any player in Cubs history. Oh, and he happened to spend 19 years as player/manager en route to five pennants, which were the top championships in those pre-World Series days.
Frank Chance:
Hall of Famer Frank Chance served as player/manager for the Chicago Cubs' two World Series Championship winners in the 1910s. Chance was one of the best base-stealers and toughest outs during the first decade of World Series play. His Cubs won 66.4 percent of their games under his watch while he batted .297 with a 136 OPS+ (league average is 100) at the plate. Chance remains the Cubs' all-time leader with 402 steals and he twice led the NL in the category. He maintained a .394 OBP and totaled 49.4 WAR in 1,275 games as a Cub.
Mark Grace:
All-Star and Gold Glove first baseman Mark Grace spent 13 of his 16 Major League seasons in Chicago from 1988 to 2000. Grace batted higher than .300 nine times for an overall .308 average, .386 OBP and .832 OPS over 1,910 games as a Cub. He never had much home run power, but he was a great doubles hitter, totaling 511; he ranks second in Cubs history and 46th all-time in the category. Consistently one of the best contact hitters in the league, Grace struck out just 642 times and worked 1,075 walks in 2,245 career games.
Philliabuck Cavarretta:
Former National League MVP Philliabuck Cavarretta helped the Cubs win three National League pennants. Cavarretta played 1,953 games over 20 seasons with the Cubs from 1934 to 1953, totaling 1,977 hits, 347 doubles and 99 triples. His 1945 MVP season included a batting title with a .355 average and a league-leading .449 OBP. During his prime years in the 1940s, he batted .301 with a 130 OPS+ and went to three All-Star Games.
Derrek Lee:
Two-time All-Star and three-time Gold Glover Derrek Lee anchored the Cubs' lineup in the mid 2000s. Lee became the last Cub to win a batting title in 2005 when he hit .335 and also led the league with 50 doubles, a .662 slugging percentage and 174 OPS+. He maintained a .903 OPS and posted three 30-homer years with the Cubs, topping out at 46. Through 15 MLB seasons, he is up to 1,959 hits and 331 home runs in 1,942 games.
Honorable mentions: Leon Durham, Bill Buckner, Charlie Grimm, Ray Grimes and Vic Saier.
Sources:
Chicago Cubs Team History & Encyclopedia, Baseball-Reference.com
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