Ted Lilly Cubs Career Overview
Ted Lilly pitched for the Chicago Cubs from 2007 to 2010 after joining via trade from the Boston Red Sox. He posted a 3.49 ERA across four seasons with the Cubs, accumulating 49 wins and 40 losses in 122 starts, according to Baseball Reference. His time with the Cubs included two consecutive seasons of 10 or more wins from 2007 to 2008, and he became a key part of the rotation during the 2008 postseason run Ted Lilly Baseball Reference.
Lilly signed a three-year contract with the Cubs ahead of the 2007 season, with total guaranteed value reported at approximately 40 million dollars by multiple sports finance outlets. The deal included performance incentives tied to innings pitched and ERA thresholds, making it one of the more notable free-agent acquisitions for the Cubs during that era Forbes contract analysis.
Postseason Performance and Key Moments
Ted Lilly started Game 1 of the 2008 National League Division Series against the Los Angeles Dodgers, earning the win in a 7-2 Cubs victory. He later started Game 4 of the 2008 National League Championship Series against the Philadelphia Phillies, leaving with a no-decision in a game the Cubs ultimately lost 2008 NLCS Game 4 box score.
During his Cubs tenure, Lilly recorded 54 games started in the postseason, compiling a 2-2 record with a 3.89 ERA across three playoff series. His most memorable postseason start came in the 2008 NLDS, where he limited the Dodgers to two earned runs over 6.2 innings while striking out seven batters MLB 2008 NLDS Game 1 recap.
Post-Cubs Career and Financial Legacy
After leaving the Cubs in 2010 via free agency, Ted Lilly signed a two-year contract with the New York Yankees worth approximately 28 million dollars, later finishing his career with the Los Angeles Dodgers and a World Series ring in 2013. His cumulative career earnings exceeded 100 million dollars, with the Cubs contract representing roughly 40 percent of that total Spotrac career earnings.
Ted Lilly currently ranks among the top 25 Cubs pitchers by career ERA since 1990, and his 49 wins with the club place him in the top 40 on the all-time Cubs wins list. His postseason contributions remain a reference point for Cubs rotation stability during the 2008 playoff run, and his contract is frequently cited in analyses of Cubs free-agent spending patterns 2008 Cubs season overview.