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In appreciation of Jon Lester

The lefthander represents an era in Cubs history never before seen.

Getty Images

It’s instructive to remember that Jon Lester signed with the Cubs even though the Giants not only offered him more money, but literally sent Buster Posey to Lester’s Atlanta-area house to say, “I want to be your catcher for the next six years.”

Why, then, did Jon sign with the Cubs? In part, it was his long relationship with Theo Epstein and the Cubs front office people transplanted from Boston. Epstein wasn’t Boston’s GM when Lester was drafted in the second round in 2002, but after he took that position later that year, Theo helped shepherd a young Lester through a bout with non-Hodgkins lymphoma and steer his career toward the success he had with the Red Sox.

Theo convinced Lester to sign with the Cubs by saying, essentially, that the Cubs were serious about winning “right now” — in 2015 — not years down the road. A video was produced showing Lester pitching in Game 7 of the World Series for the Cubs — well, what do you know, that actually happened.

It should also be remembered that when Lester came to the Cubs, he was good, really, at only one thing: Pitching baseballs. He had a reputation as a poor fielder, as a pitcher who couldn’t hold runners, and, even though batting didn’t happen that often for him as an American League pitcher, as a guy who couldn’t hit. At all. In his time in the AL, he was 0-for-34 with 22 strikeouts. Yikes.

Through hard work he managed to improve his abilities in all three of those areas, for which he should be given a lot of credit.

Even so, when he first put on a Cubs uniform, the results weren’t great. In April 2015 he made four starts and posted a 6.23 ERA and 1.569 WHIP and some Cubs fans were asking, “Is this the great pitcher Theo supposedly paid for?”

But for the rest of the 2015 season, Jon was outstanding — 28 starts, 2.99 ERA, 1.069 WHIP — and a complete-game win against a tough Pirates team September 15 in Pittsburgh when the team really needed it.

He was even better in 2016, posting a 5.6 bWAR season with 19 wins, a 2.44 ERA and 1.016 WHIP, and a second-place finish in Cy Young Award voting. Then he outdueled Johnny Cueto in Game 1 of the Division Series against the Giants with eight shutout innings, and gave the Dodgers just two runs in 13 innings in the NLCS. His outstanding pitching in Game 5 and Game 7 of the World Series is one of the unsung reasons the Cubs won. (The photo at the top of this post is from Game 7.)

Jon wasn’t quite as good in 2017, but put together another fine season in 2018 (3.32 ERA, 1.310 WHIP, 3.0 bWAR, ninth place in Cy Young voting). Injuries ruined his 2019 season and while his overall numbers in 2020 don’t look great, there was a reason for that, as I wrote in this article saying the Cubs should re-sign him:

Lester vs. White Sox: two starts, 7⅓ innings, 18.41 ERA, 2.455 WHIP, five home runs
Lester vs. all other teams: 10 starts, 53⅔ innings, 3.35 ERA, 1.174 WHIP, six home runs

Just keep him away from the Sox, or any team with righthanded power, and he can still be an effective MLB starter. That means re-signing him is likely as a fourth or fifth starter, with money commensurate, and perhaps skipping starts against teams like that. But given Jon’s experience and leadership qualities, I think it’d be worthwhile keeping him around for another year, maybe two.

I mentioned the things Jon didn’t do well before he came to the Cubs. He was a lousy fielder, but learned how to field his position well, even if he had occasionally throw his glove (with ball inside) at Anthony Rizzo:

Holding runners on? Teams learned that you couldn’t do that:

Bunting? How about this famous walkoff bunt against the Mariners in 2016?

And if the universal DH continues going forward, this home run by Lester last year [VIDEO] will be the last-ever homer by a Cubs pitcher.

For his part, Lester wants to return:

And management clearly would like to have him back:

I hope the Cubs and Lester, who was paid a $10 million buyout Friday that won’t count against the 2021 luxury tax, can come to an agreement for him to return in 2021, maybe even 2022. I believe that he has something left in the tank, and on a personal level I don’t want Jon’s last start in Wrigley Field to be in an empty ballpark. His six years with the club mean so much to the franchise, and to us as fans.

Beyond that, look at what he did for Cubs fans Friday:

Look what a bar that wasn’t even part of this did:

And here’s what Jon’s charitable efforts over the last six years accomplished:

The signing of Jon Lester brought someone to the Cubs we’d never quite seen before — a player steeped in victory (two World Series titles, a no-hitter) and someone dedicated to charitable work in the community. His signing, along with other savvy moves by Theo & Co., brought us the World Series championship all of us had dreamed of, forever.

Hope you’re back, Jon. If not... thanks, most sincerely, for the memories.