Chicago Cubs: Which ‘modern’ teammates will have their number retired?

Chicago Cubs’ Jon Lester

As mentioned above, Lester shares his number with Kerry Wood, and Lester has developed his own legacy. He represents the start of the run the Cubs have been on since 2015. When he agreed to a six-year contract in the 2014 offseason, it meant that the Cubs were ready to compete, and have they competed. The Cubs won 90+ games four seasons in a row, made the playoffs four seasons in a row, made three straight appearances in the NLCS, and capped it off with the championship win in 2016.

The days of Lester in a Cub uniform, as well as this core, are ending in two or three years, and the  Cubs need to find a way to get back to the postseason whenever baseball resumes. Maybe a possible shortened season will help the Cubs in their quest to get back to the playoffs, who knows.

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In his five seasons with the Cubs, Lester has posted a 3.54 ERA in 159 starts, and he also won the MVP of the 2016 NLCS along with Baez. Lester also recorded his first Major League hit, extra-base hit, and a home run with the Cubs. He’s hit a home run in each of the last three years.

His best days are likely behind him, though, and he gave up his highest hit total as a Cub in 2019, but the ball was massively juiced last year, and that may have played a factor. 2020 is the final year of his contract, and there is a vesting option for 2021, which doesn’t look likely. It’s very possible that he has thrown his last pitch as a Cub, and possibly his final pitch in the Major Leagues.

Lester is a borderline Hall of Famer, and he should definitely be honored in the Cubs Walk of Fame and his number flag above the outfield walls. He deserves that much for all he’s done as a Cub. If this is it for him, all we can say is thank you.