Jon Lester, 36, is probably in the final year of a free agent contract that has aged as well as he has. When you sign a guy like Lester to a six-year deal, you hope to get the best years up front and maybe win a championship (check, check), and then you hope he can age gracefully and still provide you with value in the middle or back of the rotation for the remaining years (check so far).
I say it’s probably the final year of Lester’s deal because there’s a team option for 2021 that would amount to a $15 million decision for the Cubs ($25 million deal, $10 million buyout), but when you consider the AAV implications, it seems unlikely that the Cubs will pick that up barring a monstrous season – the kind of season that might trigger the option automatically anyway (200+ innings and it kicks in (Lester hasn’t hit that level since 2016)).
That is to say, unless Lester absolutely explodes this year at age 36, he’s probably hitting free agency for the second time in his career.
But hey, he sure does look physically really good in camp, doesn’t he? And would you completely rule out a guy like Lester – with his skill and craft and knowledge and competitiveness – putting together a season that justifies giving him 200 innings?
Lester did put together another really solid season in 2019, with peripherals that strongly suggested he was the victim of at least a little bad luck. His expected wOBA was a touch better than what he actually gave up, and his LOB% and BABIP were also a touch higher than would’ve been justified by the quality of contact:
Despite that, he still gave the Cubs 171.2 innings of nearly 3-WAR baseball with a near league-average ERA.
This is a great read from Steve Greenberg at the Sun-Times on Lester, his life, his career, his teammates, and his manager. You should very much check it out today.
Lester talks about his sporting life, and how he was perceived as a future solid number three starter or so, and how that motivated him to compete. The motivation is still strong, and he wants to get to 30 starts again this year, for the 13th season in a row.
“I like my teammates to know that, every five days, I’m going to be there for them,” he told Greenberg. “That’s something I pride myself on, something I work toward. I want everyone in the Cubs organization, and especially everyone on that field, to know that, when my turn comes, I’m going to be running out there and giving it everything I have.”
I doubt anyone has ever thought anything else. And in a sport where so much of the ultimate success is found at the slimmest of margins, it’s never going to hurt a guy like Lester to be extra competitive, to take every possible (legal!) advantage, to prepare and work like no one else. Whatever happens this year, we’ll always look back on Lester thinking these things. It’ll make for some very fond memories.
But it’s not over yet. Lester is here for at least one more year, and when he can make Kris Bryant drop a swear (even if he’s only quoting someone), then clearly, he’s still doing something right.
“When I first got here, I was like, ‘This guy’s so mean,’” Bryant said of Lester, per the Sun-Times. “He just mean-mugs you all the time. But as I got to know him, I realized how unbelievable the guy is in everything that he does. He’s provided so much for this organization and team, and people want to say he’s on the downturn? I see this guy every day. Just because it could be his last year, he’s not like, ‘I’m good.’ He’s like, ‘No, I’m going to make this the best damn year I’ve had here.’ I would never bet against Jon Lester.”