Jon Lester doesn’t have an official nickname, at least not one that I could find. Throughout his career, he’s been called many things, though nothing has managed to stick. The one that has most exemplified his career is Big Game Jon. That same nickname also spells out nicely the quagmire in which Lester finds himself: deciding when to depart amidst a shift in skill where one can no longer live up to their on-the-field persona.
Before becoming a member of the Chicago Cubs, Lester was a top of the rotation starter. He performed well in big games and had been an integral member of many different playoff teams in Boston. When the Cubs signed Lester he moved from being an integral part of a rotation to the anchor of a staff. Whenever things got bad it was Lester who was expected to bring the team back on track. It was Lester who was designated as both Chicago’s skid stopper and streak starter. Most importantly, Lester was installed as a leader on a young team full of promise.
Lester proceeded to live up to every expectation the Cubs had for him throughout his six-year tenure in Chicago, a match that worked splendidly. He immediately helped turn the Cubs into a playoff team and perennial contender. Big Game John brought a World Series trophy to the North Side of Chicago for the first time in 108 years. After that, he remained a steady hand, helping lead the team to the playoffs in three of the next four years.
Lester’s final line in Chicago, at least through 2020, includes a 3.64 ERA in 1002 2/3 innings pitched, a 115 ERA+, and 13.2 rWAR in the regular season. In the postseason Lester put up a 2.51 ERA in 68.1 innings. His cWPA in 2016 was 4.8 percent in the National League Division Series, 11.1 percent in the NL Championship Series (where he was named co-Most Valuable Player), and 3.5 percent in the World Series.
If Lester were still the 2015-2016 version of himself there would be no question about teams wanting to add him to their rotation this offseason. However, Lester has shown clear signs of decline in the past few seasons.
He has always been a pitcher known for the occasional awful game, but those awful games have increased in each of the past three seasons. Meanwhile, his cumulative metrics also show a pitcher who is not what he once was. In 2017 his ERA ballooned to 4.33, and while he was able to get it back to under 3.50 in 2018, he followed that with consecutive seasons of 4.46 and 5.16. In 2019 he led all of Major League Baseball with 205 hits surrendered and his ERA+ dropped below 100 for the first time since 2012.
2020 represented a transition year for Lester. He fully lost his Big Game moniker as the Cubs moved Lester down in the rotation and rode the arms of Kyle Hendricks and Yu Darvish into the playoffs. During those playoffs, Lester didn’t see the field in either game the Cubs lost and it’s questionable that he would have seen the field if they had forced a third game. The reality that started to form a few years ago and finally set in fully last season is that father time has caught up to the former Cubs ace. It’s hard to fool opposing hitters when your fourseam fastball has lost so much velocity that you now rank in the bottom 6th percentile of all MLB pitchers.
The easy course of action would be to say that the sun has set on Lester’s career. That is the case if he still thinks he is a top of the rotation arm. However, if Lester is willing to buy into being a fifth starter and a fifth starter only then he would be a great addition to some playoff contender. It’s likely that his time with the Cubs is done no matter what, but dropping an innings eater (170+ in 12 of his 15 MLB seasons) at the back of a rotation would help any team that is playoffs bound. I’m not sure if Lester would accept such a role, but the reality is that if Lester still wants to pitch for an MLB team that is the role he will have to accept moving forward.