Red Sox Stay Quiet at Winter Meetings - and It Might Cost Them
The Boston Red Sox came out swinging early this offseason, making noise with the Sonny Gray trade and the curious swap that sent Jhostynxon Garcia to Pittsburgh for Johan Oviedo. Those early moves suggested that Boston, under new chief baseball officer Craig Breslow, was gearing up for a busy Winter Meetings.
But instead of building on that momentum, the Red Sox hit the brakes. While the rest of the league shuffled the deck, Boston mostly stood pat - and in a market where hesitation can cost you, that’s a risky play.
The Winter Meetings weren’t exactly a frenzy across the board, but a few missed opportunities stand out for the Sox. Let’s dig into four key areas where Boston may have misstepped.
1. Missing Out on Pete Alonso
If there was ever a time to make a big swing, this was it. Pete Alonso was sitting there - a power bat who could slot right into the middle of Boston’s lineup and offer some insurance with Triston Casas still a question mark health-wise. The fit made too much sense.
The reported holdup? Contract length.
Alonso was believed to be seeking a seven-year deal, a commitment the Red Sox clearly weren’t comfortable with. But when he signed for five years and $155 million, and with the division rival Orioles no less, that had to sting.
Baltimore is already trending up, and now they’ve added one of the most consistent power hitters in the game.
With Alonso off the board, the options for a true middle-of-the-order slugger are dwindling fast. And if Breslow doesn’t make a move soon, Boston could be left scrambling for Plan C - or worse.
2. Failing to Clear the Outfield Logjam
Boston’s outfield situation is a classic case of too much of a good thing. Jarren Duran, Ceddanne Rafaela, Wilyer Abreu, Roman Anthony, Masataka Yoshida, and Kristian Campbell - that’s a lot of names vying for limited playing time. And that’s not even factoring in Garcia, who was just shipped out but had been in the mix.
The Red Sox have been linked to potential outfield trades for months, and the logic is clear: move one or two of those guys to address needs elsewhere and create roster flexibility. Yet here we are, post-Winter Meetings, and the logjam remains.
Waiting for the free-agent market to settle - particularly with names like Cody Bellinger and Kyle Tucker still out there - might be the rationale. But the trade market for players like Duran or Abreu isn’t tied to those stars. Small-market teams have been sniffing around, and Boston may have missed a chance to strike while interest was high.
The longer the Sox wait, the harder it could be to find the right deal. And with roster space at a premium, that hesitation could hinder other potential moves.
3. Letting Steven Matz Walk
This one flew under the radar, but it could come back to bite Boston. Steven Matz was sharp after arriving at the trade deadline, posting a 2.08 ERA in 21.2 innings. He looked like a guy who could be a key left-handed piece in the bullpen - or even a swingman if needed.
Instead of re-signing him, the Red Sox let him walk, and now he’s with the Tampa Bay Rays. That’s not ideal.
Boston’s left-handed bullpen depth is thin. Aroldis Chapman is the only proven southpaw in the mix, and Jovani Morán - who threw just four big league innings last season - is hardly a sure thing. Justin Wilson might also be on the way out, which makes the Matz decision even tougher to justify.
Left-handed relief help is still available, but Matz had already proven he could handle the Boston spotlight. That familiarity matters, especially in high-leverage spots. Letting him walk - and to a division rival, no less - feels like a missed opportunity.
4. Passing on a Kyle Schwarber Reunion
Kyle Schwarber came off the board before Pete Alonso, so you can understand why the Red Sox might not have been as aggressive here. But still - this was a bat that could’ve made a difference.
Sure, the fit wasn’t perfect. Masataka Yoshida is locked into the DH role, and Schwarber’s glove at first base is, generously, a work in progress. But when you’re staring at a 56-homer bat, sometimes you make the fit work.
Boston didn’t even make a formal offer, despite reported interest. Meanwhile, the Orioles - again - were in the mix and pivoted quickly to Alonso when Schwarber didn’t bite. That kind of decisiveness is what Boston lacked at the Meetings.
There are still power options out there - Eugenio Suárez, and the Japanese stars Munetaka Murakami and Kazuma Okamoto come to mind - but each comes with more question marks than Schwarber or Alonso. The other route?
Swinging big on a trade for someone like Ketel Marte. That might be what it takes now to recover from these early offseason whiffs.
Final Thoughts
The Red Sox didn’t need to win the Winter Meetings, but they couldn’t afford to sleep through them either. With glaring needs at first base, in the bullpen, and on the power front, Boston had chances to make meaningful improvements. Instead, they left Nashville largely unchanged - while rivals like Baltimore got better.
There’s still time. The offseason is far from over.
But the margin for error is shrinking, and the market isn’t going to wait forever. If the Red Sox want to contend in 2026, the next few weeks need to be about action - not just evaluation.