The Red Sox have been focused on the future for a while but that future became the present in 2025. They responded with a very aggressive offseason, making many notable additions to the lineup and pitching staff.
Major League Signings
2026 spending: $17MM
Total spending: $137MM
Trades and Claims
Option Decisions
Notable Minor League Signings
Extensions
Notable Losses
- Alex Bregman, Lucas Giolito (still unsigned), Steven Matz, Justin Wilson (still unsigned), Rob Refsnyder, Dustin May, Liam Hendriks, Nathaniel Lowe (non-tendered), Josh Winckowski (non-tendered), Chris Murphy, Brennan Bernardino, Richard Fitts, Cooper Criswell (waivers), Jhostynxon García, Vaughn Grissom, Hunter Dobbins, Jordan Hicks, David Sandlin, Kyle Harrison, Shane Drohan
The Sox have essentially been rebuilding since the Mookie Betts trade in early 2020. They did quite well in 2021 but were around a .500 team in the three seasons after that. In that time, young players like Jarren Duran, Wilyer Abreu, Ceddanne Rafaela and Brayan Bello established themselves as valuable contributors, but the focus remained on a core of prospects consisting of Roman Anthony, Marcelo Mayer, Kyle Teel and Kristian Campbell.
Teel was flipped to the White Sox as the headliner in the Garrett Crochet trade last offseason. The other three all cracked the majors for the first time in 2025. Campbell and Mayer weren’t overwhelming in their debuts. The long-term outlook on Campbell is now a bit concerning but Mayer’s struggles may have been related to injury, as he battled wrist issues and ultimately required surgery. Anthony’s debut was excellent and he looks like a star in the making.
The Sox went 89-73 last year and earned a Wild Card spot. Though they were knocked out by the Yankees, that performance and the arrival of their prospects indicated they had moved well into win-now territory.
Before the offseason could even begin, the front office took a hit. In September, the Nationals plucked assistant general manager Paul Toboni and made him their new president of baseball operations. It appears that the Sox were planning to promote him to general manager, which would have cemented him as the #2 guy on the front office masthead, under chief baseball officer Craig Breslow. Instead, he became the #1 guy in Washington. Boston’s GM search appears to be on pause.
Once the offseason began, Breslow was clear that adding to both the lineup and rotation would be priorities. Though the Sox had a good season in 2025, there were some clear holes. They were giving starts to Dustin May and Walker Buehler late in the year despite both pitchers having ERAs near 5.00. Prospects Connelly Early and Payton Tolle were pushed to the majors even though they had barely pitched at the Triple-A level. Lucas Giolito became a free agent at season’s end. The struggles of Campbell and the Triston Casas injury left them weak at second and first base. Alex Bregman triggered his opt-out, opening a hole at third. Shortstop would at least have continuity, as Trevor Story decided not to opt out of his deal.
It didn’t take long for the rotation to be addressed. A few weeks into the offseason, the Sox reached a deal with Chaim Bloom, who is now the president of baseball operations of the Cardinals. It’s rebuilding time in St. Louis, which meant established veteran players were available. The Sox acquired Sonny Gray for younger pitchers Brandon Clarke and Richard Fitts.
Gray is still a good pitcher but he wasn’t needed in St. Louis. He’s 36 years old and going into the final guaranteed year of his contract. Some Boston fans were underwhelmed when looking at Gray’s age and his 4.28 ERA last year, but there are reasons to be optimistic. His strikeout, walk and ground ball numbers were all strong. His ERA may have been inflated by poor luck on batted balls, which is why his 3.39 FIP and 3.29 SIERA look much nicer.
Though the results have still been good, the contract was tricky, even beyond his no-trade clause. Gray’s deal was backloaded, paying him $35MM in 2026, followed by a $30MM club option with a $5MM buyout. That means he was guaranteed $40MM. The Cards ate $20MM of that to make the deal work and Gray agreed to a slight bump. His contract was reworked at part of the trade so he now gets $41MM, in the form of a $31MM salary and $10MM buyout on a mutual option.
Swallowing that kind of money was enough for the Cards to not just flip Gray but also get a notable return. Fitts is a useful depth starter with options in the near term. With the Sox planning to make rotation upgrades, he was going to get pushed down the depth chart to a point where he would have limited utility.
Clarke is potentially the long-term prize. He hasn’t yet reached Double-A and walks a ton of guys. He still needs a lot of polish but he has high-90s velocity and gets strikeouts. Given his uncertain future, he’s exactly the kind of prospect who should be going from a win-now club to a rebuilder. The Sox get a reliable near-term upgrade while the Cards get the long-term gamble.
Shortly thereafter, the Sox made another rotation addition, once again from an old friend. They made a five-player trade with the Pirates, who are now run by general manager Ben Cherington. The headliners in the trade were Johan Oviedo going to Boston and Jhostynxon García heading to Pittsburgh. García is an exciting upper minors prospect but has no path to playing time in the crowded Boston outfield, so the Sox cashed him in for another arm.
Oviedo is far less established than Gray but there’s intrigue there. He seemed to break out as a viable mid-rotation or back-end guy in 2023 when he gave the Bucs 177 2/3 innings with a 4.31 ERA. He missed 2024 recovering from Tommy John surgery, came back in 2025 and looked even better, though in a small sample. He only made nine starts last year but had a 3.57 ERA and 24.7% strikeout rate. His walk rate was high but that may have been rust after his long layoff. Due to his missed time, he is only making $1.55MM this year and can be controlled via arbitration for one more season.
Before the holiday break came, the Sox circled back to Bloom. This time, it was for a lineup addition, with the Sox getting Willson Contreras. The former catcher made a pretty smooth transition to first base last year. Defensive Runs Saved put him just a hair below league average. Outs Above Average put him six above par. The defensive switch didn’t impact his offense, as he slashed .257/.344/.447 for a wRC+ of 124.
His contract situation wasn’t as onerous as Gray’s, as he was owed $41.5MM over two years. The trade ended up structured similarly, though the Cards only ate $8MM this time, a reflection of the fact that Contreras’s deal was closer to market value. Like with Gray, it was restructured to pay him an extra $1MM.
Once again, the Sox flipped out a useful depth starter. Like Fitts, Hunter Dobbins was going to end up down the depth chart, so was sent to a club with more room. Prospects Yhoiker Fajardo and Blake Aita were also included and could be the more notable pieces in the long run. But neither has reached Double-A yet and Fajardo hasn’t even turned 20 years old. As with Clarke in the Gray deal, the Sox have exchanged long-term wild cards for a near-term upgrade, landing the right-handed power bat they’d made a priority entering the winter.
As the calendar flipped to 2026, the Bregman question hung in the air as he remained unsigned and the Sox still had infield holes to address. Many felt that a return to Boston was the most likely outcome but it was not to be.
Bregman settled for a short-term, opt-out-laden pact last offseason but was now hoping to cash in. Breslow has shown an aversion to long-term deals. Bregman’s three-year deal was the longest free agent contract on Breslow’s ledger, as of the start of this offseason. The Sox did make Bregman a long-term offer this time but watered it down. Reportedly, the Sox got to $165MM over five years but with deferrals stretching decades into the future. Instead, Bregman went to the Cubs. That five-year deal also has deferrals but seemingly to a less extreme degree, and with a better sticker price of $175MM.
It’s a bit of an odd look for Boston, in the grand scheme of things. They signed Bregman a year ago and pushed Rafael Devers off third base, upsetting the face of their franchise. The relationship was apparently so damaged that Devers later spurned a request to play first base when Casas got injured. The Sox responded by shipping Devers to the Giants. Presumably, the Sox didn’t anticipate the dominoes falling that way when they signed Bregman. Regardless, the end result is that they completely abandoned their future with Devers in order to get one year of Bregman, then let Bregman slip away by losing a bidding war by a marginal amount.
They didn’t have time to ruminate on that big picture stuff and quickly pivoted. When Bregman turned down their offer, they seemingly just gave all that money to Ranger Suárez. A few days after the reports of Bregman joining the Cubs, the Sox and Suárez agreed to a five-year deal. The $130MM sticker price for Suárez was south of the $165MM offer to Bregman, but the former came with no deferrals. The exact net present value of the Bregman offer isn’t publicly known but his Cubs’ deal came with an NPV of around $150MM. Assuming that Boston was offering more extreme deferrals, the NPV would probably have been pushed pretty close to what Suárez accepted. Regardless, it set a new benchmark for Breslow, as he blew past his aforementioned free agency limits.
The Suárez signing bolstered what was already a very strong rotation. He is not a dominant pitcher, with his fastballs averaging in the low-90s last year, but he clearly knows what he’s doing. He posted a 3.20 ERA last year with a solid 23.2% strikeout rate, excellent 5.8% walk rate and strong 46.8% ground ball rate. Dating back to 2021, he has a 3.25 ERA.
Boston still had work to do and the specter of the Devers trade would again hover around their next two moves. The first one was effectively a salary dump. They flipped Jordan Hicks to the White Sox, with Chicago taking on $16MM of the $24MM left on that deal. In order to move that money off the books, Boston sent out pitching prospect David Sandlin and two players to be named later. They did get back one prospect and one player to be named later, but this was mostly the Sox selling Sandlin to save money.
The next deal was not about financial concerns. The Sox addressed their infield by acquiring Caleb Durbin from the Brewers. They also added some infield depth by netting Andruw Monasterio and Anthony Seigler in the same deal, in addition to a Competitive Balance Round draft pick (#67 overall). Durbin had a solid rookie season in Milwaukee with a contact approach, rarely walking or striking out. He stole some bases and his defense was good. He doesn’t have a lot of power but his profile could play well at Fenway Park. He’ll take over at third base while the Sox will give Mayer a shot at second. Free agent signee Isiah Kiner-Falefa offers cover at both position in a utility role.
The Sox sent three players to Milwaukee, including starters Kyle Harrison and Shane Drohan. The inclusion of Harrison had some echoes of the Quinn Priester trade. The Sox had acquired Priester from the Pirates, watched him post some mediocre results for a bit, then traded him to Milwaukee. Priester immediately flourished with the Brewers after the deal. In this case, the Sox acquired Harrison as part of last year’s Devers trade. His results last year were so-so. Now he’s been traded to Milwaukee and will open the season in that club’s rotation. Time will tell if he’s as immediately successful as Priester.
Though Devers was sent to San Francisco less than a year ago, the trade tree has already shot up to the canopy. The Sox got Hicks, Harrison, James Tibbs and Jose Bello in that deal. They quickly flipped Tibbs to the Dodgers to get Dustin May last year. May was a rental, so he’s gone. With Hicks and Harrison sent out this winter, Bello is the only player in the deal still in the system. Baseball America doesn’t consider him one of the top 30 prospects in the system. Boston did get Gage Ziehl and a player to be named later in the Hicks deal but had to give up Sandlin and two players to be named later. The Milwaukee deal brought in three players but also sent out three, so the branches of the Devers deal will keep spreading out for years to come.
Another key component of the Boston offseason was something they didn’t do. With Anthony’s graduation to the majors, the outfield felt crowded, with Rafaela, Duran and Abreu all in the mix, in addition to Masataka Yoshida. It felt possible that the Sox would flip someone out of that group, most likely Duran or Abreu, but they never did. It seems they will try to find playing time for the four primary outfielders by using the designated hitter spot. That could leave Yoshida as an overpaid bench bat, at least until an injury opens up some playing time.
There has been a lot of roster turnover when looking at the past year but it all adds up to put the Sox in what seems like a good position. They have a lot of young and controllable pieces in the lineup and rotation. They have enough outfield depth that they would still be in a good spot even if there’s a significant injury. They have one of the best rotations in the league. Injuries will inevitably pop up but Tolle is waiting in Triple-A. Kutter Crawford and Patrick Sandoval could get healthy during the season. Casas could also be in game shape in the coming weeks. Perhaps injuries will open a path for him but he could also end up as a notable deadline trade chip now that Contreras is at first.
The AL East is tough to predict. All five teams feel like contenders but they can’t all make the playoffs. Some team will hit roadblocks and end up having a disappointing year. It happened to the Orioles in 2025 and the Blue Jays in 2024. There are no guarantees for any club but the Sox appear to be in a decent position to stay strong over a long season.
How would you grade the Red Sox’ offseason?
Photo courtesy of Andrew West, Imagn Images
