From June 4, 2020: Trenni Kusnierek and John Tomase debate whether the decision by the Red Sox to move on from Jon Lester in 2014 is team ownership’s biggest regret.
One of the best postseason pitchers in recent major league history is calling it quits.
Former Boston Red Sox and Chicago Cubs left-hander Jon Lester announced his MLB retirement Wednesday morning, telling ESPN's Jesse Rogers his body can longer hold up over a full MLB season.
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SIGN UP HERE "I'd like to think I'm a halfway decent self-evaluator," Lester told Rogers. "I don't want someone else telling me I can't do this anymore. I want to be able to hand my jersey over and say, 'Thank you, it's been fun.' That's probably the biggest deciding factor."
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Lester split the 2021 season between the Washington Nationals and St. Louis Cardinals, posting a 4.71 ERA over 141.1 innings at age 37. But the lefty hurler is best known for helping both the Red Sox and Cubs win World Series titles with a grit and resolve that translated to stellar postseason numbers.
A second-round draft pick of the Red Sox in 2002, Lester overcame a battle with lymphoma as a rookie in 2006 and a year later pitched 5.2 shutout innings in Boston's World Series-clinching win over the Colorado Rockies in 2007. He also threw 7.2 scoreless innings in Game 1 of the 2013 World Series against the St. Louis Cardinals.
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Lester earned three All-Star nods and won two championships over eight-plus seasons with the Red Sox before they controversially traded him and Jonny Gomes to the Oakland Athletics in 2014 for Yoenis Cespedes and a draft pick. The move would come back to haunt Boston, as Lester joined the Cubs in 2015 and thrived in Chicago, collecting two more All-Star appearances and winning three games for the Cubs during their 2016 World Series run.
Lester boasts a 2.51 career postseason ERA and ranks in the top 10 all-time in postseason innings pitched (ninth, 154) and postseason strikeouts (ninth, 133). His regular-season numbers aren't too shabby, either: 200 wins over 16 seasons with a career 3.66 ERA and 2,488 strikeouts.
