Grading the Boston Red Sox's 2025-26 Offseason

The Boston Red Sox offseason has been one of the more contentious among fans in recent memory. Promises of acquiring Pete Alonso and of retaining Alex Bregman went south as soon as the Winter Meetings began. Despite these letdowns, the Red Sox made substantial upgrades to their pitching staff, adding Sonny Gray, Johan Oviedo, and Ranger Suarez while also getting some much needed lineup support in the form of Willson Contreras and Caleb Durbin.

Much of the frustration stems from the gap between expectations and reality. Boston failed to add a legitimate 30-plus home run bat, and for a team that finished 22nd in MLB in strikeouts last season, the offense saw little meaningful improvement. There is an argument to be made that swapping out Bregman for Contreras and Durbin is, at best, a lateral move.

However, despite the narrative of being a "cheap" big-market ballclub, among their 14 transactions (12 trades, 2 MLB signings), the Red Sox spent roughly $161 million dollars thus far in the offseason, with potential moves still in the works. 

So, how did the Red Sox do this offseason? Are they a better team than the one that was eliminated by the Yankees in the Wild Card? The answer is unequivocally yes.

Grading Every Red Sox Offseason Move

Trade: Sonny Gray for Brandon Clarke, Richard Fitts, and PTBNL or cash

The Red Sox's first major move of the offseason was acquiring what appeared to be, at the time, their second option in the rotation in Sonny Gray. A model of consistency despite his age, Gray continues to make batters uncomfortable, striking out at least 24% of opposing hitters since 2018, thanks to his deadly sweeper, which continues to grade out as one of the best in baseball.

Fans might see his 4.26 ERA in 2025 and be frustrated with the return; his FIP and SIERA both indicate a bout of poor luck relative to his other seasons, but the Cardinals ate some money off his contract in this deal. That makes this deal represent minimal risk. He's one of the best third options in baseball and should thrive in his new environment. 

Regarding the return, Fitts was able to show what he had in the major leagues and never really excelled despite being an analytics darling. He returned a 12.3% K-BB% and recorded a 5.00 ERA. The real piece in this deal was trading away Brandon Clarke. Some may remember his hot start to the season, posting a 45% strikeout rate in April. After a blister in his hand, he was never really the same, and most prospect analysts tab him as a high-leverage reliever, which is useful in its own right but not someone worth clutching your pearls on if you're in the position the Red Sox are in. He was buried on the pitcher depth chart and had little chance of breaking into the majors in 2026.

Trade Grade: B+

Trade: Johan Oviedo, Tyler Sameniego, and Adonys Guzman for Jhostynxon Garcia and Jesus Travieso

Johan Oviedo is a classic Red Sox pitching lab play, plain and simple. While his numbers don't jump off the page, he was not acquired for his 2025 ERA, though his 3.57 mark in 40 innings of work is not a reason for discouragement. Oviedo will make his hay due to his unusual release point paired with elite extension. It is a combination that hitters have had a tough time gauging, causing whiffs on his fastball.

Coming off Tommy John surgery, Oviedo lowered his release height, causing a new and more elite fastball shape, which clearly intrigued the Red Sox enough to trade one of their top five prospects in Garcia.

Garcia also got a cup of coffee in the majors, not doing much with it, but the power is evident. In updated top-100 prospect lists, he appeared toward the bottom or not at all. This is largely due to his poor swing decisions, sporting a 26.1% chase rate and striking out 55% of the time while up with the big league club. While the raw power is real, the discourse all offseason has been about the logjam in the outfield for the Red Sox, and that includes Garcia, who was likely the fifth or sixth option behind the established major leaguers. Ultimately, he was expendable, particularly for a pitcher they believe they can optimize.

Regarding the other three prospects, the jury is still out, though none of them cracked either team's top-30 prospect lists. By all accounts, Guzman is a warm body available to catch innings in the low minors.

Trade Grade: B+

Trade: Willson Contreras for Hunter Dobbins, Blake Aita, and Yhoiker Fajardo

Contreras filled a clear need at first base with Triston Casas' health an enigma, and the Red Sox did not want to force Nick Sogard and Romy Gonzalez to platoon at the position. Their infield defense was also bottom of the league last season. Contreras and his six Outs Above Average will provide a huge help on that front.

Contreras, like his Cardinals teammate Sonny Gray, is remarkably consistent. Since 2021, he has hit 20 or more home runs in all but one season and has recorded 2.0 fWAR or more in every season since then. His move to first base last year will help keep him on the field, as he reached 135 games played, his most since 2018. 

Dobbins is a pitcher who had promise and a potential spot on the roster come Opening Day. He put together 61 solid innings of work in his rookie campaign with a 4.13 ERA and a 6.6% walk rate. The problem lay in his strikeout rate, which came in at a measly 17.6%, which works if you're able to keep the ball on the ground at an elite level. While 48.4% ground ball rate is not bad by any means, it's not enough to warrant full trust in the arm moving forward. I would have liked to see what his season would have looked like had he not torn his ACL in a freak accident while covering first, but that is the world we live in, and it's likely part of the reason the Red Sox felt okay with parting with him. 

Aita is not much of a loss, but Fajardo is a high-potential arm who profiles as a flamethrower at only 19. 

Trade Grade: B-

Free Agent Signing: Ranger Suarez for 5 Years, $130M

After reeling from the loss of Alex Bregman to the Cubs, the Red Sox responded with their first signing of the offseason, bringing in Ranger Suarez. He was not the typical arm the Red Sox targeted this offseason, as he offers minimal height, extension, and velocity. He instead found success forcing soft contact and controlling the strike zone. Suarez returned a 4.0 fWAR last year, a career-high, and a 3.20 ERA, his lowest since 2021. 

One note of concern is that his fastball velocity has been trending the wrong way over the last three years, starting at 93.4 mph, 92 mph, and then 91.2 mph. Based on results from the Red Sox aforementioned pitching lab, though, I believe that the Red Sox can reverse that trend and get it back up to around 93 mph or so. 

Nonetheless, the signing officially made the Red Sox one of the scariest rotations in baseball and moved them above everyone in the division except for the Blue Jays. Because of that, I consider this signing a huge success, though the lineup still leaves a lot to be desired. 

Signing Grade: A-

Trade: Caleb Durbin, Andruw Monasterio, Anthony Seigler, and Comp Round B pick for Kyle Harrison, David Hamilton, and Shane Drohan

In a wild six-player trade a day before pitchers and catchers reported to camp, the Red Sox got their middle infielder in Caleb Durbin, who can play both third and second base. Durbin does not provide crazy power, something the Red Sox still need. But he is a fantastic contributor in four of the other five tools necessary to be a successful position player. He rarely strikes out (9.9% K%), swiped 18 bags thanks to his 70th-percentile sprint speed, and is an above-average fielder at third (5 DRS, 2 OAA). 

Monasterio provides similar utility ability to Isiah Kiner-Falefa, playing 10-plus games at 2B, 1B, and SS, while also getting eight games at 3B in 68 games in the majors. He profiles as a platoon hitter against lefties, hitting southpaws to the tune of a 136 wRC+ with a .837 OPS, whereas against righties it was a 96 wRC+ and a .709 OPS. Monasterio's place on the team come Opening Day will be determined by his performance in the spring, but expect him to start in AAA and be one of the first options up.

Seigler crushed Triple-A pitching last season, slashing .285/.414/.478 walking 16.9% of the time and stealing 23 bags. He didn't play catcher except for one game in MLB, being stuck behind William Contreras, but he is a potential option to catch this season. 

The biggest piece that the Red Sox gave up in this deal was Kyle Harrison, as another Devers trade piece was shipped off. Much like the rest of the high-profile pitchers that have been dealt, there was little room for Harrison in the Red Sox's future plans. The emergence of both Payton Tolle and Connelly Early held him back, as Harrison threw only 12 innings for Boston last season. The ceiling is there for Harrison, a former top-25 prospect, though it became clear as the 2025 season wore on that the Red Sox were no longer interested in finding that ceiling.

Drohan projects as fringe rotation option/middle relief arm ranking around 15th on most lists on the Red Sox farm system. He sits mid-90s with his fastball and has multiple above-average offerings. His primary issue is the inability to stay healthy which saw his prospect stock drop over the years.

Fans are plenty familiar with David Hamilton, a solid glove with plus speed. Beyond that, he mostly just caused headaches for Sox fans when he stepped into the box, hitting .198 in 2025 with a .590 OPS. 

Trade Grade: A

The rest of these moves are not as significant, so I won't cover them as in-depth as the rest, though they still added to (or subtracted from) the future outlook of the 2026 team.

Trade: Isaiah Jackson for Vaughn Grissom

This was a necessary move as both parties were ready to move on from each other. With the plethora of injuries that decimated the infield over the past few years, one would have assumed that Grissom's time would come at some point, but it just never arrived. They clearly preferred other options over him, and the Kristian Campbell puzzle still needed solving. Lost in the Betts and Devers shuffle, Grissom was acquired for Chris Sale, who would go on to win a Cy Young the season immediately after. A disastrous move all around. 

Trade: Ryan Watson for Justin Reimer

A Rule 5 trade that was largely ignored, Watson provides solid upside for a Triple-A arm, sporting a 28.1% strikeout rate and a 7.1% walk rate last season, which gave him a 21% K-BB% (99th percentile in Triple-A). Watson, standing at 6'5, provides seven feet of extension, making him an obvious fit for the pitching lab. Watson is a name to keep an eye out for if the Sox need some mid-season bullpen help. 

Trade: Jake Bennett for Luis Perales

This was a rare prospect-for-prospect deal. Bennett, similar to Watson, stands at 6'6 with elite velocity and extension. Because he is in Double-A, we have little in the way of advanced metrics, but he fits the mold that the Red Sox sought out this offseason. He is a top-10 prospect in the Red Sox's farm system and cruised last year with a 2.27 ERA and 1.08 WHIP. 

Perales will be sorely missed, looking like he has the potential to be one of the league's top closers, sitting 97-98 mph and touching 100. 

Trade: Gage Ziehl and PTBNL for Jordan Hicks, David Sandlin, 2 PTBNL, cash

This trade struck a chord with me. For one, the Wicked Witch is gone, as Hicks simply did not mesh with the Red Sox once he was acquired. On the other hand, we salary dumped our salary dump. It all comes back to Rafael Devers, who remains sorely missed on this Red Sox team. The trade is greater than Hicks, who I'm glad is gone, but never should have been on the team in the first place.

David Sandlin has been an intriguing prospect for a while now, but he did not seem to cut it as a starter and did not take to his new role in the bullpen. A brutal 6.7% K-BB% won't fly at any level you're at, but sitting close to 97 mph certainly will. I'll be curious to see what the White Sox do with him as his career unfolds. 

Ziehl, a fourth-round draft pick in 2024, provides some upside, controlling the zone well with average stuff on all of his offerings. The real win here for the Red Sox was getting off the Hicks contract, not the prospect they got in the deal.

Free Agent Signing: Isiah Kiner-Falefa for 1 Year, $6 million

Not the middle infield signing fans wanted, but Kiner-Falefa fills a hole and opens up things in the lineup for the Red Sox. He is a clear glove-first signing, providing little in the way of power, but has above-average Defensive Runs Saved numbers at 2B, 3B, and SS. His versatility will allow Alex Cora to play more matchups or give guys some needed rest as the season moves forward. As I said in the linked article, regular playing time for Kiner-Falefa means something has gone terribly wrong in 2026.

In an eventful offseason full of various moves, it's clear the Red Sox got better. The question is, how much? That will largely be determined as the season unfolds. If I had to give it an overall grade...

Final Grade: A-