Boston Red Sox

BOSTON, MA - OCTOBER 23: Jon Lester #31 of the Boston Red Sox tips his cap as he leaves the game in the eighth inning against the St. Louis Cardinals during Game One of the 2013 World Series at Fenway Park on October 23, 2013 in Boston, Massachusetts. (Photo by Jared Wickerham/Getty Images)

It’s been almost eight years since the Red Sox traded Jon Lester away, but the lefty’s achievements in Boston left a permanent mark on the city.

Lester is retiring after 16 seasons in the major leagues, as first reported by ESPN’s Jesse Rogers and confirmed by WBZ-TV’s Dan Roche. The first half of his career was spent entirely with the Red Sox. Lester went 100-56 with a 3.76 ERA in 221 regular season appearances in Boston. But his biggest moments came in October.

Starting with two of his three career World Series titles in Boston, Lester was one of the best big-game pitchers of his time. Over six career appearances in the World Series, he went 4-1 with a 1.77 ERA and 34 strikeouts in 35 2/3 innings. Overall, he was 9-7 with a 2.51 ERA in the postseason.

After Lester had two shaky regular seasons to start his career, his first major accomplishment came in the 2007 World Series, when he hurled 5 2/3 shutout innings against the Colorado Rockies in the series-clinching Game 4. He emerged as a top-of-the-rotation force in 2008, when he went 16-6 with a 3.21 ERA. A no-hitter against the Kansas City Royals that season signaled his arrival.

Lester won at least 15 games in five of six seasons from 2008-13, and was a major piece of the Red Sox’ run to a World Series championship in 2013. If not for David Ortiz batting .688 with two homers and six RBIs, Lester would have won series MVP: 2-0, 0.59 ERA against the St. Louis Cardinals.

The Red Sox ultimately traded Lester to the Oakland A’s as part of a deal that brought Yoenis Cespedes to Boston in 2014. Lester’s lone postseason start with the A’s was a disaster, but he re-established himself after joining the Chicago Cubs in 2015. He made three appearances in the team’s ghostbusting 2016 World Series win, two starts and one out of the bullpen. After losing Game 1, he won a must-have Game 5 when the Cubs were down 3-1 in the series, then allowed one run in three innings during the decisive Game 7. Lester was also the 2016 NLCS MVP, when he posted a 1.88 ERA over two starts.

Is Lester a Hall of Famer? He’s most certainly done enough to earn a spot on the ballot in five years. He finishes his career with exactly 200 wins and a 3.66 career ERA to go with three world championships and an LCS MVP award to his credit. The one knock on him is that he never won a Cy Young award. He came in second place in Cy Young voting in 2016 (19-5, 2.44 ERA) as the tough-luck loser to Hall of Fame lock Max Scherzer.

I like to keep it simple: if Mike Mussina and Bert Blyleven are Hall of Famers, Jon Lester is. But we’ll see if the actual voters agree down the road. Whatever happens, nothing can take away from Lester’s postseason accomplishments in both Boston and Chicago.

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Matt Dolloff is a writer and podcaster for Any opinions expressed do not necessarily reflect those of 98.5 The Sports Hub, Beasley Media Group, or any subsidiaries. Have a news tip, question, or comment for Matt? Yell at him on Twitter @mattdolloff and follow him on Instagram @mattydsays. You can also email him at