The Chicago Cubs are in a similar spot to the Red Sox. Coming off a recent championship that needs an infusion of fresh young talent. The only difference is, Boston is in a much better spot for a quick turn around. Jon Lester is now that cagy veteran that has been part of the Red Sox and Cubs championship team. When given the choice in the offseason, Lester needs to come back home and finish his career with the Red Sox.
Lester, 36, is under contract with Chicago for the 2020 season for $20 million. For the 2021 season, the Cubs and Lester have a mutual option worth $25 million. Lester needs to pitch 200 innings this year for that option to trigger. All incentives would be prorated if a season takes place.
Regardless, it probably doesn’t matter because the Cubs would probably prefer Lester to take the $10 million buyout. Chicago has Kris Bryant, Anthony Rizzo, and Javier Baez to take care of. They already have bad contracts with Jason Heyward and Yu Darvish on the books. They’re going to need that extra cash.
Given that, it’s going to be messy to work out a deal. Chicago will have to pay him the $10 million buyout already. How do you make a new contract work for an aging player that probably isn’t worth $10 million at this stage of his career.
Boston becomes the obvious choice with a clear spot for him in the rotation. David Price was shipped out in the Mookie Betts trade. They need to fill that hole. What better way than to do so with Jon Lester. The Red Sox actually have a path to return to a championship contender quickly. They got young assets in the Betts deal and will reset the tax in a big way.
It’s time for Lester to come home. To be part of one more Red Sox championship team. A team that he grew up with and the one he can finish his career with. What’s a better way for a swan song career than sweet Caroline.