Chicago Cubs: Is Jon Lester the best Chicago free agent signing ever?

Chicago is widely recognized as one of the biggest sports town in the world. But did the Chicago Cubs make the biggest move of all in signing Jon Lester?

When the Chicago Cubs inked veteran southpaw Jon Lester back in the winter of 2014, every baseball fan knew the team was getting serious about winning. The deal was for six years, totaling $155 million, with an option for a seventh year.

There is no doubt the impact Lester has had on the Cubs. He has been an ace for all four seasons, despite his age. With two years left on the deal, there is enough of a sample to wonder where he ranks amongst Chicago sports lore.

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Marian Hossa is another name that we can put on this list. Hossa only helped guide the Blackhawks to three Stanley Cups and create a borderline dynasty, no big deal or anything.

You look at the 90s’ Bulls teams, most of those guys were homegrown with the exception of their best free agent signing: 34-year-old Dennis Rodman. Khalil Mack might be the best grab by the Bears ever. Plus, technically he wasn’t a free agent, so for right now we will leave him off.

Since coming to the Cubs, Lester has made 128 starts, with a 3.33 ERA. He’s thrown 770 innings, given up just 690 hits, struck out 733, with a 3.67 FIP, and posted a 12.4 WAR with the Cubs in four seasons. That’s an ace if there ever is one.

The more important numbers are the playoff numbers. In the postseason, Lester has made 12 appearances, including 10 starts. In 70 innings, he has given up just 50 hits, 60 strikeouts and just 17 walks. Not to mention, he ended the longest World Series drought in sports history while winning the co-MVP of the 2016 NLCS along with this season’s breakout star, Javier Baez.

Lester will always have a place in Cubs’ lore and he wouldn’t have to pitch another game. Right now, he is definitely in the top five of all time free agent signings. If this team can win a second World Series ring with Lester anchoring the rotation, then there isn’t a doubt where he ranks at the top of the list.

Hey, who’s to say the Cubs don’t add Bryce Harper and a few more and go get that second ring? Well, a fan can hope the Cubs make a splash this winter, right? Oh well, there’s no use Harping on the topic.