Chicago Cubs: No. 2: Jon Lester
I understand that one could make the case that either Jake Arrieta or Kyle Hendricks was the best Chicago Cubs pitcher of the decade. Yet I have Jon Lester ranked as the highest pitcher – and no. 2 overall – because of what his arrival meant for this franchise along with what he has accomplished in a Cubs uniform.
The Cubs battled a few different teams to obtain Lester’s services prior to the 2015 season, and when the left-hander chose the Cubs, it was perhaps the club’s biggest step forward (except for bringing in Joe Maddon to manage) in becoming a contender. In his five years with the team, Lester has made 32 starts every year (except for 2019, when he made 31) and has been, for the most part, the anchor that the rotation needed.
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Lester was solid in his first year with the Cubs in 2015, posting a 3.34 ERA. However, just like many of the Cubs’ players, 2016 was when he really shined. His 2.44 ERA helped him to place second in NL Cy Young award voting, while he posted a 2.02 ERA in six postseason appearances. Lester wasn’t quite as good in 2017 or 2018, though he still was a reliable starter who also pitched well in the postseason.
Lester showed signs of age in 2019 and wasn’t as effective as he’s been in the past. However, I think just about any Cubs fan will tell you that his contract was worth it and that he’s perhaps the best free agent signing in Cubs history.
Lester has one year left on his contract with the Cubs (although there is a team option for 2021). It’s looking like his best days are behind him, though thanks to what he helped to accomplish with the Cubs, he will always be a legend on the north side of Chicago.