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Jon Lester retires, ending a 16-year career that included 3 World Series titles with the Chicago Cubs and Boston Red Sox

cigaretteman

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May 29, 2001
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One of the most pivotal free-agent signings by a Chicago franchise is closing the book on his career.

Former Cubs left-hander Jon Lester announced his retirement Wednesday via ESPN after 16 big-league seasons that featured 200 wins and three World Series titles with the Boston Red Sox and Cubs. Lester, 38, spent the 2021 season with the Washington Nationals and St. Louis Cardinals, departing the Cubs following 2020.

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Lester signed a six-year, $155 million contract with the Cubs in December 2014, a big move that subsequently helped the organization appear in four consecutive postseasons (2015-18). He earned MVP honors in the National League Championship Series in 2016 en route to the Cubs winning the World Series in a memorable seven-game series against Cleveland to end a 108-year title drought.

Lester’s career resume should put him in consideration for the Baseball Hall of Fame as one of the best left-handed starters of his era. He posted a 3.66 ERA, 2,740 innings pitched, 117 ERA+, 1.278 WHIP, won three World Series, was a five-time All-Star and had three top-five finishes for the Cy Young Award, including runner-up in 2016.

Lester earned his 200th career victory Sept. 20 before closing out his career with two starts against the Cubs.

 
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Jon Lester has 200 career wins, was 5 Time All-Star
and won 3 World Series Championships. The fact
that he was a crafty lefthander who had a bull-dog
approach to pitching should help him get into the
MLB Hall of Fame. His overall stats do not impress
you, but his big heart and competitive spirit should
make him a consideration for Cooperstown.
 
This will be interesting in five years. He was a damn good pitcher. But was he a HOFer? Is being a great postseason pitcher on three title teams enough to counter decent but not eye-popping career statistics and no major awards?
 
I still can't believe Boston traded him at the end of a contract year and fans really thought he would sign with the Sox as a free agent.
 
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John Lester might be my favorite Red Sox pitcher of all time. The man was a Red Sox warrior! His battle against cancer, as impressive ( and successful as it was) was always a “rear view mirror story” because of his ability to pitch “big games” for Boston. He was one of the first to prove a lefty could be successful in Fenway....the guy was an “ inning eater” and if given better support in the bullpen at Boston and Chicago, would have won another 20 games or so in his career.
Congrats John Lester on a job very well done!
 
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