Jon Lester announced his retirement on Wednesday, ending a 16-year career that included three World Series championships and five All-Star game appearances. Lester is also a cancer survivor and a legend in the cities of Boston and Chicago.
Lester was drafted by the Red Sox and spent his first nine seasons there. He emerged as one of the best home-grown pitchers the Red Sox ever had, winning 110 games with a 3.64 ERA while in Boston. He was also an integral piece of two World Series winning teams in 2007 and 2013.
Lester was diagnosed with cancer in 2006 and missed significant time at the end of the 2006 season and beginning of the 2007 season. Upon his return in 2007, he allowed four earned runs or more in four of his first six appearances before settling down. He had a 3.34 ERA in September and had three postseason appearances, his one start being the clinching game of the 2007 World Series when he threw 5 2/3 scoreless innings.
Following his first championship, Lester continued to pitch well, throwing a no-hitter in 2008 and making All-Star teams in 2010 and 2011.
In 2013, he helped deliver another championship to Boston. His regular season totals of 15-8 with a 3.75 ERA were good, but his postseason performance was great. Lester had five postseason starts and went 4-1 with a 1.56 ERA. His only loss was 1-0 in Game 1 of the ALCS. In two World Series starts, both wins, Lester gave up one total run. His fantastic pitching was a major reason why the underdog Red Sox were able to defeat the Tigers in the ALCS and Cardinals in the World Series.
After a contract dispute in which the Red Sox initially low-balled Lester, he was traded to Oakland at the trade deadline in 2014. His addition and 2.35 ERA over 11 starts helped the A’s make the playoffs.
Lester signed with the Cubs in 2015 and once again found himself at the center of a contending team. The Cubs won their first world series in 108 years in 2016 due in large part to Lester having the best season of his career and once again being brilliant in the postseason. Lester went 19-5 with 2.44 ERA with 197 strikeouts in the regular season. In the playoffs, he pitched in six games (five starts) and the Cubs won five of them. He went 3-1 with a 2.02 ERA. His two World Series appearances were a Game 5 win when he gave up two runs in six innings and the clinching Game 7 win when he pitched three innings of relief and gave up two runs, one earned.
Lester added one more All-Star appearance with the Cubs in 2018 and finished his career in 2021 with both the Nationals and Cardinals.
Lester is a Hall of Fame pitcher by any measure, but his postseason performances put him among the legends. His 1.71 Division Series ERA and 1.77 World Series ERA showed his performance heightened as the stage got bigger. He was the winning pitcher in two World Series clinching games. Beyond the field, Lester was an inspiration to cancer sufferers everywhere and a universally liked and respected teammate. It should not be long before he has a plaque in Cooperstown.