Building the best Chicago Cubs starting rotation by WAR

Houston Astros v Chicago Cubs
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4. Greg Maddux 33.7 WAR with the Cubs

Although his wins above replacement with the Cubs seems low compared to his whopping career WAR of 106.6, Greg Maddux's first string of seasons with the Cubs from 1988-1992 were still some of the most impressive ever seen on the North Side. Most notable was the 1992 Cy Young winning year, where Maddux hurled a league-leading 268 innings with a 2.18 ERA. This would be the first of four consecutive Cy Young awards for Maddux (tied for an all-time record), although the other three were when he pitched for the Atlanta Braves.

Still, Maddux's contributions to the Cubs are remembered enough to have his uniform number 31 retired by Chicago as well as Atlanta. After his historic tear for the Braves, Maddux returned to the Cubs on a three-year deal and his second stint lasted from 2004-2006. Should Maddux have pitched the entirety of his career in Chicago, he would easily be the best pitcher in team history. However, the next guy on this list takes that honor.