Cubs News: Jon Lester’s most memorable moments

This could be the final season in a Chicago Cubs uniform for starting pitcher Jon Lester.

With the conclusion of this shortened 2020 season rapidly approaching comes the talks of a possible last dance for the core group of the Chicago Cubs. We have heard all season how this could be the final run for the players we saw rise to the big leagues and raise a World Series trophy. However, one key member of this group was already an established name before joining the team and has made his presence known on the mound–Jon Lester.

Lester, 36, will become a free agent if the team declines a $25 million option for next season.

In 2015, Cubs President of Baseball Operations Theo Epstein signed Lester to a six-year/$155 million deal, which signified the end of a rebuild, and the start of what turned out to be five playoff appearances and a World Series title.

Along with other new veterans, Lester’s presence rubbed off on the young up-and-coming players. The first time a lot of them played with a former champ’ and seeing him go about his business each day made them want to reach that same level.

I would argue the signing of Lester is the best free-agent acquisition in the history of this storied franchise. He hasn’t exactly been a Cy Young award winner when looking at his statistics, although he did place second in 2016, whenever the team needs a big start on the mound, he finds a way to come through in the clutch.

Jon Lester career with Cubs: 170 games (77-43) 3.59 ERA 999 IP 937 SO 289 BB (2x All-Star)

His last start in Pittsburgh is a perfect example of this. The Cubs needed to end a two-game losing streak with a lackluster offense, so what does Big Jon do? Throws six innings of shutout baseball en route to a 5-0 win.

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Has he struggled at times this season? Definitely, but he is 36-years old in his 15th major league season, and he isn’t going to be the same ace he once was. Giving the team the type of outings like his last time out is more than you could ask for at this point in his career.

Even with that being said, there are still many pitchers I would take him over in the playoffs, as his track record speaks for itself.

Jon Lester Playoff Statistics: 26 games (9-7) 2.51 ERA 154 IP 133 SO 40 BB (3 WS Titles)

You don’t need to throw 100 mph or have the nastiest stuff to be effective in the postseason; just ask Clayton Kershaw. At the end of the day, you need to outsmart opposing hitters and execute pitches, which Lester can still do when it counts.

It is more than likely the team will decline his option for next season, but maybe they can reach an agreement to bring him back on a friendly deal.

Granted, he will have at least one more regular start and probably another in the postseason, but for now, let’s take a trip down memory lane as we look back at some of his most significant moments as a Cub.