Jon Lester just gave more of a s–t than you

Three-time champion with Red Sox and Cubs announces his retirement after 16-year career

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Few players willed his teams to victory the way Jon Lester did.
Few players willed his teams to victory the way Jon Lester did.
Illustration: Getty Images

Sadly, the, “You’re not winning this game,” term used to describe a transcendent performance from an athlete that just seems a Herculean or galactic level of defiance and denial has been co-opted by Bill Simmons. Which means it’s become as cartoonish as he has.

It happens.

But still, there are few things more riveting to watch as a fan than one player not only taking over a game, but seemingly dragging teammates as awestruck as we are watching along with him while denying the opponents a whiff. LeBron in the last three games of the 2016 Finals. Jarome Iginla’s “shift.” John Elway’s “The Drive.” Carli Lloyd in the 2015 World Cup Final. 

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These are classics, but every fan has their own catalog of not just historic performances, but ones that come along with such an emphatic door-closing that they become something else entirely. One player standing above the rest, where the outcome of the game is simply decided by them.

Jon Lester, who announced his retirement today after 16 seasons and three rings, has those. He has them both in Boston and Chicago. Lester’s tale is accented by overcoming cancer as a rookie to starting and winning the clinching game of the 2007 World Series. It was only enhanced six years later, when over two World Series starts, Lester threw 15.1 innings and gave up a single run to the Cardinals, striking out 15 against one walk in the process and stripping them of any hope that they might overcome the Red Sox. With the series tied 2-2 it felt poised for anything. By the time Lester was done in Game 5, he himself had opened such a gap between the teams there could only be one winner come Game 6.

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Lester’s stuff wasn’t great. It was hardly bad, but it didn’t pop off the screen the way Justin Verlander’s or Clayton Kershaw’s did. A good fastball that he could locate on either side of the plate. A better-than-you realized change-up without being the Bugs Bunny version that Johan Santana would feature. And a curve that he honestly probably should have used more.

Lester made up for it with expert location and expertise, and quite simply a will that was unmatched. Sometimes it felt like Lester, when he was at his best, would just stare a hitter down until they just wilted. He could put up monster strikeout games, but he didn’t need them. Broken bats, weak grounders, and harmless flies were more than enough. And when he was on, it felt like he just conjured those simply because he wanted to more than the hitter wanted to make solid contact. There was a bloody-mindedness to it. Lester just kept moving forward, no matter what was thrown at him or what he was hit with. He barely reacted.

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Lester’s rep as a stone-cold killer was already in place when his Red Sox career came to an end, but it was elevated to deity-status in Chicago with the Cubs. He’ll go down as probably the best free-agent signing in Chicago sports history, and really only Marian Hossa might have an argument. But when you are maybe the major reason 108 years of sadness, comedy, and pain are ended, it’s pretty much the end of any debate.

And that comes down to simply three games, three starts in the 2016 playoffs. Make no mistake, Lester was brilliant through all of 2016, which is why he finished second in the Cy Young voting, the closest he would ever get to the award. As the reigning Cy Young champion, teammate Jake Arrieta, began to fade, Lester canceled that out (with some help from Kyle Hendricks, I have to point out or my two best friends will knife me). 202.2 innings, a 2.44 ERA, an ERA+ of 59 (100 is average, lower is better), nearly a 4-to-1 strikeout-to-walk ratio.

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But none of that would have mattered without the three starts in October. The first came in Game 1 of the NLDS against the Giants. It was not a vintage Giants team, but they still had all that #EvenYear cache, the last Giants team to win the World Series wasn’t that impressive either, and they had Johnny Cueto on the mound. We’d already seen Cueto with the Reds be a fucking problem for years for the Cubs to have our stomachs marching with urgency toward our throats before a pitch was thrown. And Cueto had been just about as good as Lester that year.

Make no mistake, even with the 103-win juggernaut that the 2016 Cubs were, had Cueto beaten them in Game 1 with Madison Bumgarner waiting in Game 3, this city would have absolutely gone over the deep end. All the gremlins and ghouls would have come out. And it probably would have translated to the team itself. We’d seen it before, too many times to count.

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Lester didn’t care. The Giants got one runner to second on him over eight innings. And even as Cueto was matching zeroes, Lester’s steeled confidence and defiance spread through to the Wrigley crowd, and even the jitteriest fanbase felt assured. Lester wouldn’t let them score, we’ll find a run. Javy Baez did in the eighth. Off on the right foot. Just follow Jon.

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The next came in Game 5 against the Dodgers in the NLCS. Again, not the Dodgers team you know now. But the Cubs’ bats went missing in Games 2 and 3 (including against fucking Rich Hill which I may never get over, no matter how that year turned out). They’d clawed back in Game 4, but the idea of losing Game 5 and having to win both at home, including getting past Kershaw, didn’t hold much appeal. Lester gave up one run over seven, the Cubs clobbered the Dodgers’ fading pen, and Kershaw was meat in front of a salivating city the next game. Follow Jon.

That wasn’t the last time Lester would pull the Cubs’ ass out of a sling. There was Game 5 of the World Series, and the world was ending. The Cubs were facing defeat, having been drawn and quartered not just by Corey Kluber or Cleveland’s doomsday bullpen, but by some hilljack Mike Tomlin to go down 3-1. We didn’t know if we were attending a wake or not before Game 5, because we might actually see the Cubs lose a World Series at home.

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Lester struck out the side in the top of the first, turned Wrigley back into the frenzied zoo it had been, and propelled the Cubs to a win that night (over Trevor Bauer, which will keep me warm on the coldest of nights). You know what happened then, even through his unnecessarily early relief appearance in Game 7 (Hendricks had it, Joe). Just follow Jon.

While Lester would go on to be more than solid for four more seasons, those three games are all he, or we, needed. Staring down opponents, history, fear, and telling all of it, “Get fucked, I’m on this.” He didn’t blow anyone away, he didn’t have to make them look foolish, he just kept moving forward. When it mattered most, no one could slow or stop him. He just gave more of a shit.