Overall Thoughts
As disappointing as losing to the Yankees in the playoffs was, when you step back and look at the 2025 season, you remember how much fun it was. As a result of that, the expectations for the 2026 season are high. This offseason, in my opinion, is the most important in almost a decade. Due to contacts expiring, opt-outs, and the Devers trade that has never been replaced, the Front Office has its work cut out for it.
What I Would Love
Signing Devin Williams
In my FA predictions, I had Williams going to the Red Sox. Not only have I heard that through the grapevine, but I think it just makes a lot of sense. Williams entered his 30s and “fell off a cliff” (I put that in quotations because if you look at his Chase %, Whiff %, and K%, they are still elite). But it felt like every big moment that he faced, he stumbled. At 31, no team is going to commit to a long-term deal. For me, I love the idea of pairing Williams with Chapman. It is what some fans thought Hendriks/Chapman would become.
Acquiring a Bonafide #2 Starter
We cannot go into 2026 hoping the young guys figure it out behind Garrett Crochet. Whether it is revisiting the trade talks for Joe Ryan (who has the control the Sox need) or paying up for a free agent, this rotation needs a horse. If they are trading, the rumor I love most is Hunter Greene from the Reds. The chatter is a package centered around Wilyer Abreu and prospects (like Franklin Arias). Greene is young, electric, and under team control through 2028. He is precisely the kind of “power arm” Breslow drools over.
What I Would Be ‘Mid’ About
Trading Jarren Duran
I don’t really see the point of trading Duran. The rumors linking him to the Cincinnati Reds or Kansas City Royals make baseball sense for them, but not for us. Why create a hole at leadoff just to fill a hole elsewhere? He is a spark plug that does not cost the team a lot of money. If the team saved so much money on Rafael Devers, I don’t see the need for them to trade an asset like Duran. I am significantly more okay with the team trading Wilyer Abreu. While his defense is great, he does not provide the chaos on offense that Duran is capable of.
Signing Pete Alonso
With Josh Naylor’s deal this week, I imagine Alonso would get around $120-$140 million across 5 years. While I would not be doing back flips in excitement, it has been a LONG time since the Red Sox had a solid option at first base (sorry, Triston Casas STANS.) Whether you like it or not, Alonso consistently plays over 150 games and hits bombs every year.
What I Wouldn’t Love
Trading Marcelo Mayer or Kristian Campbell
I have seen a lot of ridiculous trade proposals that have Mayer and Campbell being shipped off to other teams for some pitching help. I would be heartbroken if that were the case. There is no pitcher, outside, I suppose, Paul Skenes, that I would package these two for. The team would also be selling at a significant low point, being that both Campbell and Mayer underperformed/were injured last year.
Signing Alex Bregman To A Long-Term Deal
The type of contract he is seeking (5-7 year range) just does not make sense for this team. Bregman will be 32 years old when the 2026 season kicks off. He is already weak when it comes to Exit Velo, Barrel%, Hard Hit%, and Bat Speed, and all of these will continue to regress with age. On the defensive side, he’s still excellent, but for how much longer?
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