Amid the flaming trainwreck that is the 2026 Red Sox season, there’s this very odd side note to consider. Specially, the Red Sox actually had a pretty solid offseason.
Now, “pretty solid offseason” is intentionally vague and highly subjective, but work with me here. As we approach the season’s halfway point, it’s worth exploring the moves the club did make last winter, and how much more maddening they makes everything that’s manifesting now.
Below is a list of the eight transactions I deem to be the most significant of the past offseason. For this exercise, I’m not interested in things like the Vaughn Grissom trade or signing Danny Coulombe and Tommy Kahnle for peanuts in the bullpen. I’m trying to stick to the headliners that have moderate to major impacts on the big picture. If you disagree with the list, feel free to let me know in the comments and we can hash it out there.
So without further ado, here we go in chronological order:
1)November 25, 2025: Traded Brandon Clarke and Richard Fitts to the St. Louis Cardinals for Sonny Gray and cash.
Right out of the gate, this one looks like a win. Going into the winter, one of the biggest items on the Red Sox shopping list was a No. 2 starter after they had to go with Brayan Bello in Game 2 of the Wild Card series last year against the Yankees. Amazingly, it looks like they got one before Thanksgiving.
Gray is sitting at 9-1 and nearly a third of all Red Sox victories this year have come in his starts. The money gets complicated, and will continue to get more complicated if he is moved in the next six weeks, but I don’t think there are any Sox fans who would take back this trade.
2) December 4, 2025: Traded Jesus Travieso and Jhostynxon Garcia to the Pittsburgh Pirates for Adonys Guzman, Johan Oviedo and Tyler Samaniego.
This looks like a mostly nothing deal right now and you could even argue it doesn’t belong on the list. Jhostynxon Garcia hasn’t found success in Pittsburgh and Johan Oviedo has spent almost the entire year on the IL. For now it’s a neutral, nothing deal, but I’d have to imagine we’re going to see a decent amount of Oviedo in the second half, so I thought it deserves mention as a deal that could become relevant in the coming months.
3) December 15, 2025: Traded Luis Perales to the Washington Nationals for Jake Bennett.
Another deal for the nerds but, so far, this one is going quite well for Breslow and the Red Sox. Jake Bennett fits the big lefty, long extension mold they covet, and he’s starting to settle into the back of the rotation after also posting a 1.60 ERA in nine starts with Worcester.
Perales still has a high ceiling, but has shown no signs of getting closer to reaching it yet in 2026. Long way to go here, but so far this is looking like another positive move.
4) December 22, 2025: Traded Blake Aita, Yhoiker Fajardo and Hunter Dobbins to the St. Louis Cardinals for Willson Contreras.
The craziest thing about the Willson Contreras acquisition is how much he’s exactly what the Red Sox needed on paper, and yet it hasn’t made a lick of difference in their record. He’s right handed, he mashes, he’s having the best season of his career slugging wise, he’s filled the hole at first base, he plays above average defense, he brings a veteran presence in the clubhouse, and he takes a good at bat in high leverage spots. How has this not mattered more?
In any case, the Red Sox desperately needed a big right handed bat, and Craig Breslow managed to get one at an extremely affordable price. Contreras has an .896 OPS, which is just 30 points off the highest OPS of any right handed bat in baseball thanks to the top seven guys all being left handed and some pretty interesting evidence starting to pile up that ABS is helping the lefties (each of the top seven OPS figures in the sport right now bat left handed).
Bottom line: This was a fantastic trade!
5) January 9, 2026: Signed Tyron Guerrero as a free agent.
A total reclamation project that’s blossoming before our eyes. The goods news is he’s throwing triple digit gas for the strikes. The bad news is he’s 35 and the prudent thing to do is likely move him for future value before the deadline. Still, this looks like another win for Breslow.
6) Mid January, 2026: Lost out on the bidding war for Alex Bregman to the Cubs and immediately pivoted to sign Ranger Suarez to a five-year, $130 million deal.
Here’s the key moment of the entire offseason. Through some combination of misreading the market, not locking Alex Bregman up earlier, and just genuinely poor communication skills, the Red Sox didn’t land their man. This led to a pivot to spend the money that was going to go to Bregman on Ranger Suarez because at that point in the offseason, there wasn’t much else left on the shelves.
On one hand, Suarez has been another excellent addition, and there’s a good chance we’re going to look back on this move extremely favorably by the time his five year contract is over. However, this also left the Red Sox with a surplus of starting pitchers and a gigantic hole at third base, which leads us to this:
7) February 9, 2026: Traded Shane Drohan, David Hamilton and Kyle Harrison to the Milwaukee Brewers for Caleb Durbin, Andruw Monasterio, and Anthony Seigler.
Undoubtedly, this is the most bitter transaction of the winter. Craig Breslow moved on from a young, cost controlled left handed starter who has been outstanding for the Brewers for a third baseman who just started hitting this month. Losing Harrison hasn’t hurt the 2026 Red Sox all that much as their issue isn’t in the starting rotation, and you can kind of see how Durbin was supposed to fit into the puzzle with his defense, but there’s no way to classify this other than a huge loss at this stage.
They better hope Durbin keeps hitting!
8) February 10, 2026: Signed Isiah Kiner-Falefa as a free agent to a one year, $6 million deal.
It’s certainly not a move I would have made (they needed to shoot higher), but at that price and with this team’s holes, he’s been fine as a utility man. If he comes off the IL quickly, the front office will probably be able to get a lottery ticket return for him at the deadline.
Adding all that up, again I say, “pretty solid offseason.” The biggest issues here are the moves he didn’t make. Breslow didn’t move Jarren Duran for 80 cents on the dollar to clear the outfield logjam. He didn’t move on from Brayan Bello when the had the surplus of pitching following the Ranger Suarez signing, and he didn’t go aggressively enough after another right handed bat. (Although to be fair, the right handed bats available have proved incredibly underwhelming. Even if you wanted Pete Alonso at first base, that means no Willson Contreras.)
Still, despite those warts, it’s feels borderline impossible the Red Sox are having the season they’re having in 2026 with that offseason coming off 89 wins in 2025. Then again, if you watch them play every night, you know the real issue here is they just don’t know how to play baseball as a collective unit. They don’t come back in games, they don’t pick each other up, they don’t take good situational at bats, they’re downright dreadful in clutch situations, and despite being well above average overall defensively, they manage to make their errors at the most inopportune times and almost never make a highlight reel play to save a game.
Long-term, this characteristic is a complete disaster and enormous changes are needed throughout the organization since being able to play baseball as a cohesive unit is kind of the whole point of the sport. However, when it comes to just the 2026 trade deadline, that doesn’t really matter. Unlike in the offseason where piling up value on a roster where the pieces don’t fit will absolutely come back to bite you in the caboose, it’s pretty much the name of the game if you’re a seller at the trade deadline.
You can be picky, you can drive the price up, and you can wait out for offers that will make your counterpart squirm because you have all the leverage. This is exactly the type of negotiation Craig Breslow is made for. So instead of swapping everything else out in the next few weeks and letting somebody new handle this on the fly, isn’t it better to let Breslow have the deadline and then radically alter the organizational philosophy after August 3rd?
Again, take a look at the offseason he had. Breslow is good at collecting value. Despite the unmitigated disaster this club has been on the field in 2026, he’s probably still the best man for this job for at least six more weeks.
Beyond that though, it’s going to take a much bigger reclamation project to fix the issues that permeate deep inside the organization. While sellers at the deadline play a game on paper, the rest of the league, as this front office has learned the hard way, does not.
