Jon Lester Says He Wans to Be Back with the Chicago Cubs Next Year

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Jon Lester Wants to Be Back with the Chicago Cubs Next Year – But Wants to Win One This Year First

Chicago Cubs

Lost amid everything else in the world, there wasn’t much talk in the run-up to last night’s game about it possibly being Jon Lester’s last start for the Chicago Cubs at Wrigley Field. Maybe we just didn’t want to think about it.

For almost six years now, Jon Lester has been a rock in the Cubs rotation, frequently dominating, always bouncing back from the lows, and steadying those around him. His free agent signing was a clear turning of the page for this organization, and it’ll go down as one of the best free agent deals in club history. That’s pretty rare when you’re signing a post-age-30 starting pitcher to a six-year, $155 million contract.

Lester said he was dealing with a lot last night, knowing that it was possible that was it for him at Wrigley Field.

All that said, I’m not gonna go too far down this path today. For one thing, the Cubs still need some good starts out of Lester this year, even if they aren’t coming at Wrigley Field (then again, if there’s a Game Three in the opening round of the postseason, that very well COULD be at Wrigley Field and COULD feature Jon Lester).

For another thing, it’s not a lock that this is the end of the line for the Cubs and Lester, as he himself just said:

Lester’s contract calls for a $10 million buyout on a 2021 option, at which point he’s going to enter this offseason a free agent for the first time in six years. Free agency figures to be particularly unkind to non-star veterans this year, but you’ve gotta believe there’s still a job out there for Lester if he wants to keep going. No, he’s not a middle-of-the-rotation arm at this point, but as a smart, capable veteran who is great in the clubhouse and can easily be a 4/5 on a playoff contender? There’s a contract out there for him.

Will it come from the Cubs? TBD, obviously. It’s so very hard to make any predictions about this offseason given the financial situation, the post-2021 CBA talks, and what to make of 2020 player performance. I think the Cubs would probably be thrilled to keep Lester around for a number of reasons, but it will almost certainly have to be on a very modest agreement that won’t leave them feeling like – financially – they’ve locked him into the rotation for 2021.

For now, we’ll leave it there, because like I said, there’s more of this season to see unfold first. And I’m with Lester: win the damn thing in 2020, worry about the rest later.

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.