With Hot Stove season around the corner, it seemed like a good time to take some of your questions surrounding what should be a fascinating offseason for the Red Sox. Some of the questions were edited for brevity and clarity.
What do you think about Alex Bregman’s contract situation in light of the fact that many outlets, including MLB.com, have reported that he will exercise his opt-out clause after the World Series? – @Joee__03
It is a really interesting situation. Bregman got off to such a great start, then he had that right quad injury that he admirably rushed back from to help the team’s postseason push. However, his pre- and post-injury numbers are startlingly different. Given that, what kind of contract can he draw at 31 coming off a significant leg issue and a prolonged late-season slump? On the other side of that coin, how much more enticing will he be for teams on the market this winter compared to last given that he won’t have a qualifying offer attached to him this time?
I think there is mutual interest in a reunion. Bregman emerged into a leader on that team in about two hours and remained one the entire season. From what I saw, he liked the buzz of playing in Boston and the pressure that comes with it, which isn’t true for every player.
However, this is likely to be his last, best chance to get a long-term contract, so he has to weigh all the options. The one thing I’m sure about is that he won’t sign with a non-contender. This is a guy who has winning in his blood. He has never missed the playoffs. The Red Sox have certainly positioned themselves as a contender in the coming years.
Do you have any sense as to whether ownership tells [chief baseball officer Craig] Breslow ahead of the negotiations how much they are willing to spend on a given player (in this case, Alex Bregman), or if they simply wait to hear from Breslow once he has had a chance to negotiate with the agent? – @bellhorn2004
I think it is the opposite. Breslow will play the market and make the best deal he can for Bregman, and when he finds out what the ultimate price will be, that’s the point when he goes to ownership and it either gets approved or doesn’t.
Assuming health, do you think they’d prefer Marcelo Mayer at SS and Trevor Story at 2B, or the reverse? – @NewRoyalRooters
I don’t think it’s time to move Story off shortstop just yet. I know he had some issues late in the season, but he has been a shortstop for all but one season of his career and is coming off a strong bounce-back year offensively. With a full season of health under his belt and, for once, no rust going into a season, there’s a chance Story performs just as well if not better in 2026. Mayer will plug in wherever he fits best. He’s obviously an option at third if Bregman doesn’t return.
Which pitchers do you believe will be traded [by other teams] this offseason? We keep hearing about Joe Ryan, Sandy Alcantara and Hunter Greene as targets, but who do you think is the most realistic No. 2 or 3 the Red Sox will go after? – @jordan376077925
Obviously Ryan is the guy Breslow pursued the most aggressively last season. While he wouldn’t trade Jarren Duran during the season, I don’t think that would be as much of an issue in the winter. If Duran gets dealt, Breslow would have plenty of time to reshape the roster. Also, with the glut in the outfield, Roman Anthony would move seamlessly into Duran’s spot in left. Duran alone wouldn’t be enough to get that deal done. A top prospect or prospects would have to be included for a pitcher of Ryan’s caliber. Given that he would be under club control for two more seasons, it’s fair for the Twins to expect a hefty price. It sure will be interesting to see if Breslow or another team meets it.
Is Connor Wong going to be the backup catcher or will they upgrade at this position? – @the_surfing_guy
Given Wong’s offensive numbers in 2024 versus ‘25, I think it’s pretty obvious health played a big role in his downturn. Wong never made excuses, but he came back quickly from a fractured left pinkie in May and also played through a right hand injury that required surgery after the season. Wong isn’t eligible for free agency until after the ‘29 season. I think he sticks around as the backup. The catching position is one spot the Red Sox can save money at given the duo of Carlos Narváez and Wong.
Will the Red Sox pursue any free agents with qualifying offers attached, or will it depend on whether they receive an extra [Draft] pick as compensation for Lucas Giolito? And will they even offer Giolito the QO to begin with? – @Bergeron_MLB
If you see a pitcher you like -- and there should be a few on the market this winter -- I don’t think you can get too consumed with having to forfeit a Draft pick. The Red Sox are moving into a territory where they want to win now, so that could entail signing someone who received a qualifying offer, just like they did with Bregman last winter. I think the decision on Giolito will depend on if the Sox feel he is healthy. If so, I believe they will extend him a QO and then leave the decision in his hands.