The Boston Red Sox were one of the most active teams in the early portion of the offseason. Trading for Sonny Gray was one of the offseason's opening salvos, while the strange deal that sent Jhostynxon Garcia to Pittsburgh in exchange for Johan Oviedo just days before the Winter Meetings seemed to set the club up for an active time at the annual summit.
Instead, Craig Breslow stayed on the sidelines and was a bystander as the action happened around him. To be fair, the Winter Meetings were a tepid affair overall, but still, it's hard to look at what went down and see some clear blunders from Boston. These 4 stand out the most.
4 mistakes the Red Sox made at the 2025 Winter Meetings
Whiffing on Pete Alonso
For all the talk of adding a big bat this winter, along with the concern over Triston Casas' health and ability to be a productive force at first base, it seemed like Alonso and the Red Sox were a match made in heaven.
The big issue was Alonso's contract demands. The former Mets slugger was rumored to be seeking a seven-year deal that surely would've ended poorly, so when he settled for five years and $155 million, the Red Sox must have been kicking themselves. Making matters worse, he wound up with the division rival Baltimore Orioles, who are looking like one of the league's most improved clubs to date.
The drop off in terms of power bats left on the market is relatively steep, and if Breslow doesn't strike soon, he could be left out in the cold entirely.
Not making any trades to clear the outfield logjam
One of the worst-kept secrets in baseball is that the Red Sox need to trade an outfielder. Jarren Duran, Ceddanne Rafaela, Wilyer Abreu, Roman Anthony, Masataka Yoshida and Kristian Campbell make for too many cooks in the kitchen, even without Garcia banging down the door for playing time.
You can use waiting on free agents like Cody Bellinger and Kyle Tucker to settle as a reason for patience, but at the same time, with small-market clubs like the Kansas City Royals sniffing around, Bellinger and Tucker don't have much bearing on the market for either Duran or Abreu.
There's still time, but if the Red Sox wait too long, they could be left without a dance partner. Plus, the sooner they clear the roster space, the easier it will become to make additional moves.
Letting Steven Matz walk
This might seem like an overreaction, but letting Steven Matz go after acquiring him at the trade deadline smacks of a mistake. Not only was Matz lights out for the Red Sox, posting a 2.08 ERA in 21.2 innings down the stretch, but Boston has very little to replace him with internally.
The lefties currently on the roster that could factor into the bullpen mix are closer Aroldis Chapman and the uninspiring Jovani Morán, who pitched just four big league innings last season.
Having competent lefties to set up for Chapman is important, and Boston could also lose Justin Wilson. There are some remaining options that could be intriguing, but having a guy who proved he could handle Boston in Matz would have been nice. Even nicer would have been not letting him go to the Tampa Bay Rays.
Not making a serious play for a Kyle Schwarber reunion
Kyle Schwarber coming off the board before Pete Alonso makes this somewhat more excusable, but it still isn't great. Unlike Alonso, the fit isn't as clear with Yoshida clogging up the DH spot. On the other hand, is Yoshida really a reason to stop you from adding a 56-homer bat?
There was always the chance that the Red Sox could've tried Schwarber out at first base, as they did during the brief stint he actually did play in Boston. That likely wouldn't have worked out well, but if Breslow truly was looking for a power bat, there was none more powerful on the market.
Boston didn't finish among the finalists for Schwarber, and didn't make him a formal offer despite its rumored interest. Meanwhile, the Orioles did what the Red Sox should have done, pursuing Schwarber and quickly pivoting to Alonso once their advances were rejected.
There are still some thumpers left on the market, but the likes of Eugenio Suárez and the Japanese stars Munetaka Murakami and Kazuma Okamoto all bring with them more question marks than Schwarber or Alonso would have. The other option is pulling off a blockbuster deal for Ketel Marte, which might be what is necessary to make these misses sting less.