Charlie Root: 201 wins
The Chicago Cubs’ all-time wins leader is righty Charlie Root. Pitching for the Cubs from 1926 to 1941, Root became the club’s all-time leader in both wins and saves, though he has since been overtaken in the second category. In just his second season as a full-time starter, Root led the NL with 26 wins with 309 innings in 1927. He had an outstanding first-half of his Chicago career, winning 15-plus games in each of his first eight years, later combining for 61 wins in his last eight years. Charlie Root is the only pitcher to win more than 200 games in a Cubs’ uniform.
Mordecai Brown: 188 wins
A three-game winner in two World Series Championships, Mordecai Brown ranks second on the Chicago Cubs’ all-time wins list. Brown won the decisive game of the 1907 World Series for the Cubs and earned two more wins during their last World Series Championship in 1908. Nicknamed “Three-Fingers” for appropriate reasons, Brown put together one of the most dominant stretches of baseball ever pitched. From 1906 to 1910, he totaled a 127-44 record with a 1.42 ERA in 1,460.2 innings. In ten seasons with the Cubs, the Hall of Famer had a 1.80 ERA and his career 2.06 ERA is good for sixth in Major League history.
Bill Hutchinson: 180 wins
A workhorse even by the standards of his era, Bill Hutchinson sits third among the Chicago Cubs’ all-time wins leaders. Hutchinson pitched in Chicago from 1889 to 1895 with his best seasons standing out from 1890 to 1892. In each of those three years, he led the National League in starts, innings pitched, complete games, and wins; his cumulative numbers from that stretch included 1,786 innings, 121 wins, and a 2.76 ERA.
Larry Corcoran: 175 wins
A great right-handed pitcher from more than a century ago, Larry Corcoran ranks fourth among the Chicago Cubs’ all-time wins leaders. Corcoran pitched for the Cubs from 1880 to 1885 and ranked among the NL’s top five in wins in each of his five full seasons. In an era when starting pitchers carried far greater workloads, Corcoran started 60 games out of 84 played in his rookie season, winning 43 of them. He led the league in strikeouts in 1980 with 268, in wins in 1981 with 31, and in ERA in 1982 with a 1.95 mark.
Fergie Jenkins: 167 wins
Control artist Fergie Jenkins spent the prime of his Hall of Fame career in Chicago and ranks fifth on the list of Cubs’ all-time wins leaders. The Cubs acquired Jenkins in mid-1966 and in his first full season with the club in 1967, he won 20 games. He went on to win at least 20 in each of his first six seasons in Chicago, topping out at 24 in 1971 when he posted a 2.77 ERA in 325 innings to win the National League Cy Young Award. The three-time All-Star won a total of 284 games in his career and is a member of the 3,000 strikeout club.