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.

After struggling at the plate, Lester managed to become an effective hitter for the Cubs.

What a wild game this was. Down 6-0, the Cubs fought back on Sunday night baseball in a matchup that featured former Cub pitcher Travis Wood making a catch running back into the ivy in left field. They tied the game in the bottom of the ninth and eventually played into the 12th inning, setting the stage for pinch-hitter Jon Lester.

Talk about clutch. Down to his final strike and the game on the line, Lester comes through with the squeeze play for the win.

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Most Cubs fans will remember Lester’s first season with the team, where he looked miserable at the plate. Spending most of his career in the American League will do this, considering he never had to worry about batting with the designated hitter. A big kudos to Lester for putting time in the batting cages because his improvements were shown in the past few seasons.

In his first year with the Cubs, Lester managed just four hits in 62 at-bats–yikes. Lester transformed himself into a solid hitting pitcher, cranking three home runs over his last three seasons.

He even held a batting average of .188 and an OPS of .556 last season. Now that I think about it, those statistics are pretty similar to some Cubs position players we see this season, which is kind of alarming.

Not the most conventional way to get outs, but Lester found a way to get the job done.

Much like his hitting, Lester’s fielding from the mound took some criticism his first few seasons on the North Side.

For some strange reasons, Lester struggled when it came to throwing to bases on plays from the mound and even pick-off attempts. To make things even weirder, there were times when he would have to throw not just the ball, but his glove as well.

All jokes aside, a pitcher needs to be able to field to help his team win games. I remember going to a Sunday night game in 2015 against the Reds, where Billy Hamilton stole five bases during a Lester start.

As soon as teams got a runner-on against Lester, they planned on stealing a base, knowing he wouldn’t attempt a pick-off, and if he did, who knows where the ball would end up. Some would even bunt back to the mound to test him.

To his credit, Lester made the necessary improvements with the Cubs, and now you don’t see these kinds of things anymore.

In his first season with the team, Big Jon committed three errors. Since then, Lester has committed just two errors in the past five seasons combined.

It would be easy for a multi-million dollar athlete not to care as much, we see it a lot around all sports, but someone like Lester is built differently. The lefty has a competitive attitude about him that he brings to the ballpark every day, and that is why we have seen the improvements in hitting and fielding.

I think that is what I will miss the most about Lester because it is not something that can be taught, and it isn’t something every player has.

He will still have a start or two in a Cubs uniform, and knowing the competitor he is; I guarantee he will leave it all on the field.