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ESPN CHICAGO: 50 Greatest Cubs

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14. Greg Maddux

Photograph By Jerry Lai/US Presswire

Greg Maddux will forever be viewed by Cubs fans with bittersweet memories because the team let him go via free agency after he won his first of four Cy Young Awards in 1992. He was 133-112 in 10 years with Cubs, including his first seven in the bigs.