State of the offseason: Checking in on Red Sox Nation

This story was excerpted from Ian Browne’s Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

One of the best ways to find out what Red Sox fans are wondering about is to do a Reddit AMA. So that’s what I did on Tuesday. Here is a sampling of some of the most interesting questions paired with my answers. Questions and responses have been lightly edited for clarity.

Am I crazy for still feeling optimistic about this situation? I don’t have an issue with anything [chief baseball officer Craig] Breslow has done, including not spending 5/150+ on [Pete] Alonso or [Kyle] Schwarber. Of course, I wish ownership spent money a bit more, but it’s just not reality (and seemingly sometimes the smarter move). I feel like we’re trying to be the Astros, but imagine if we had signed Corbin Burnes last year instead of trade for [Garrett] Crochet.

I agree with you 100 percent. Being the voice of reason can be tough this time of year, but I'm very willing to let the offseason shake out and assess what moves they make in conjunction with the ones they’ve already made, and then judge them by that, rather than what they've done by Dec. 16.

Do you think the Sonny Gray or Johan Oviedo trade was a better move? Also, how exactly are the Red Sox prioritizing their various needs?

Gray was the safer, short-term move. The Oviedo acquisition provides upside for not just 2026, but beyond. Early in his regime, Breslow has established a pitching infrastructure that can get the most out of pitchers in their 20s. Oviedo is another test case. As for prioritizing needs, I think the obvious top need is to improve the offense. But if they are stalled by the market on that front, they will multi-task and make other acquisitions first if need be.

How serious do you think the Sox were about Alonso? He's not perfect, but seemed like a good fit. Despite what this subreddit says, I do genuinely believe they are interested when they say they are (I do think they were actually trying for Juan Soto last year), but it seemed like they weren't really trying for Alonso.

I think they were very interested in Alonso, but not for five years. They looked at a home run hitter who is regarded as a subpar defender and were hopeful they could find common ground for a three-year deal that included an option or, at the very most, they might have gone to four years guaranteed if that could have closed a deal. Keep in mind that the Mets -- the team Alonso had spent his entire career with until this winter -- didn’t make him an offer. If you remember last year, they didn't go to an eighth year on Max Fried. The Yankees did. The Sox got Crochet in a trade the next day.

Jarren Duran may or may not end up being traded away this offseason. If he is traded away, who would you like to see in the return? Whether it be a SP, Ketel Marte, or another infielder to help bolster a lackluster infield.

If you want to trade for a legit starting pitcher, I think Duran is a great way to front your package. He has three years before he is eligible for free agency. He offers power and speed, and at least 10 triples per season. I'm not saying they need to trade Duran. But I just think he's the best piece to get that front-line starting pitcher via trade.

Could you see the Red Sox trading for Willson Contreras? If so, what might the package look like?

Contreras would be a nice right-handed bat to have at a modest cost for a hitter of his caliber ($18 million in 2026, $18.5 million in '27 and a $17.5 million club option in '28). Cardinals president of baseball operations Chaim Bloom knows the inventory of the Red Sox better than most. Would he want a couple of the prospects he drafted? We already saw this in July with Blaze Jordan. Would he want a Major League player who performed well when he was running Boston's front office? (Triston Casas fits that bill). Contreras has made a nice transition from catcher to first base, so he could also help you on defense.

Does it feel like, internally, the Red Sox are viewing this as their “win now” window, or is it still a couple of years away? I've been wondering if this is the kind of thing that contributes to whether or not this offseason is the right one to commit 4-6 years to guys in their 30s.

Really good question. I think they are just entering their "win now" window. Check how the Dodgers have operated under Andrew Friedman. Once that team felt they were ready to be a World Series contender every season, their aggression on free agents really went up. I think this will increase gradually with the Sox in the coming years.