I can admit it. I ain’t got no qualms.
When it comes to impending Cubs free agents, I haven’t given Jon Lester’s situation a ton of thought yet. Obviously, that’s not because of his importance to this team – on the field or off. But when guys like Kris Bryant, Javy Baez, Anthony Rizzo, and Kyle Schwarber each have fewer than two years of team control remaining but many more years of high quality baseball production ahead of them, your priorities shift.
Nothing will take away from the fact that Jon Lester was the best free agent signing the Chicago Cubs have ever made – he led them to the World Series and nearly won the 2016 NL Cy Young award. But, there’s context: he’s already 36 years old and already under control for 2021 (his age 37 season) if the Cubs wanted him back.
Of course, given that his option for that season is a relatively significant $15M decision ($25M salary, but with a $10M buyout) and given that there have obviously been signs of decline, an extension just wasn’t on my radar. To be completely frank, I kind of wondered if Lester would just play this season out, collect his $10M buyout at the end of the year, and eventually put a stamp on a 15-year, 3x World Series champion career. And I had made peace with that.
But all that changed when I heard him talk about his ex:
“For me, I don’t know what is going to happen next year,” Lester said to WEEI’s Rob Bradford. “I know I have the team option, the [vesting] option, that sort of thing. We’ll figure that out one way or the other. I will either be here or be a free agent.” Lester continued, when asked about Boston: “Obviously everything is open. I’m open-minded to anything. Absolutely it would be cool to go back and finish my career where it all started. But, I’ve got a little time before I really have to sit down and weigh that decision, even if it’s something where they want me back. Hopefully, I’m still a good enough caliber pitcher that the want of my services will still be out there for people. We’ll see.”
Okay, now I’m jealous.
When I thought Lester was going to retire as a Cubs and set off into the sunset, I cared not. He made his money, he’s earned his rings, etc. Go enjoy it all. You’ve earned it. But even as only his adopted team, I don’t think I want to see him in another uniform ever again.
Altogether, Lester has spent six full seasons (and three partial seasons) with the Red Sox and five full seasons (plus whatever 2020 is going to be) with the Cubs. There was also a half-season with the A’s, but whatever. The Red Sox also drafted him and he won two World Series while he was there. So I get it. The Cubs are not really his team. Not the way Boston will forever be. But I guess I’d just prefer it if he stuck around until the end.
Which brings me back to his contract.
Is Lester going to be worth $25M in 2021? Almost certainly not. But again, it’s really a $15M decision for the Cubs. Unfortunately, in this case, I’m not sure that any of that will actually factor in. As an extremely well-respected veteran who doesn’t need the money and has an excellent relationship with this front office – the one that originally drafted him in Boston, no less – Lester will probably have an unusually big sway over his future. And by that I mean, I think the Cubs front office would be more flexible with him than they would with nearly any other player (in terms of letting him go, picking the option up, staying on a little longer, etc). It’s not going to be carte blanche, obviously, but he’ll have his say. That much I believe.
Now we just have to wait and hope he rather finish things out in Chicago than return to Boston where it all started.
Not that he’s necessarily going to retire any time soon: