Black Friday (and beyond) Shopping List, 2025 Red Sox Edition

Whether or not you’re personally observing a Black Friday boycott this year, Craig Breslow has some shopping to do. We’ve already seen him wheeling and dealing, trying to make the moves we need to get past the first round of the 2026 postseason. Thanksgiving was late this year, so that means the holiday shopping season is short. Better get going, Craig Breslow. [Consults list.]

Do what it takes to re-sign Alex Bregman. Probably five years, $160M.

The price was right on Sonny Gray but I wouldn’t classify him as a Number Two Starter. Craig Breslow might, but if he does that means I’ve bought into his off-season schtick again.

How about Framber Valdez near the top of our rotation for a contract in the neighborhood of six years and $168M? With the groundballs he generates, it’s a good thing we already have Bregman in our shopping cart—and that the Sox as an organization will lean more into defense moving forward.

Can we still hold out hope for Joe Ryan via the trade route? Yes, because with a Triston, a Tristan, and two Grays on the roster—not to mention a surplus of outfielders—the Sox have some duplicate items and I predict they’ll be making some returns.

But let’s continue shopping.

I have mixed feelings about our first-base situation due to my love for Triston Casas. I want to see him get a chance in 2026, but let’s at least window shop Pete Alonso. Looks like as much as five years at $125M, but can maybe get done for less?

I’m considering Bo Bichette, but until we actually get past the checkout with Bregman (“Only 1 available, and it’s in 4 other carts”), I’m not sure. If Bregman doesn’t return, let’s get Bichette at third base. There’s room for him at second (maybe?) if we clear room in the outfield and commit to keeping Ceddanne Rafaela in centerfield, where he belongs.

Please and thank you, Craig Breslow.