14 of Jon Lester’s best Cubs moments during six-season tenure

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Tim Stebbins
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14 of Jon Lester’s best moments with Cubs originally appeared on NBC Sports Chicago

Jon Lester’s incredible Cubs tenure has come to an end.

After six seasons on the North Side, Lester has agreed to a one-year deal with the Nationals, NBC Sports Chicago’s David Kaplan confirmed Monday.

Lester, 37, signed a lucrative six-year deal with the Cubs during the 2014-15 offseason. His addition helped push a team that had finished fifth in the division the previous three seasons to contention status. 

The Cubs made five postseason appearances during Lester’s time with the club, including trips to the NLCS in each of his first three seasons. One of those, Cubs fans will never forget, resulted in a fateful World Series championship. 

From 2015-20, Lester won 77 games and posted a 3.64 ERA. He made 30+ starts in five of his Cubs seasons, a shortened 2020 being the lone exception. He made two All-Star teams (2016, 2018) and was named the 2016 NLCS co-MVP.

Lester played a pivotal role in turning the narrative around on the North Side, and for that, he’s rightfully considered the greatest free agent signing in Cubs history. 

As he heads to the nation’s capital, here’s a look back at some of his best moments in a Cubs uniform.

14 of Jon Lester’s best moments during Cubs tenure

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