Craig Breslow was extremely active on the trade market last offseason. The Boston Red Sox made 13 trades before the 2026 campaign, which involved 36 different players.

Most were not blockbuster trades, and a few didn’t even involve major leaguers, but that is still a rash of trades that, a season later, can be reviewed and regraded with the benefit of a full season under all the players’ belts.

Re-grading all of Craig Breslow’s Red Sox trades from the 2025-26 offseasonRed Sox acquire RHP Sonny Gray from the Cardinals for LHP Brandon Clarke and RHP Richard Fitts

Grade: A+

This was easily Breslow’s best move of the offseason. Gray’s value was down after a rough 2025 campaign and his contract was large. The Red Sox sent an injury-prone but high-potential pitcher, Brandon Clarke, to the Cardinals, plus a depth starter/long relief option in Fitts. He also got the Cardinals to pay down some of his contract.

Gray’s performance in 2026 makes this trade an A+ no matter how good Clarke and Fitts become. Breslow was able to identify a veteran whom he knew his pitching staff could make tweaks to and help return to form. No one expected a career year from Gray, though.

Red Sox acquire 1B Willson Contreras from the Cardinals for RHP Hunter Dobbins, RHP Yhoiker Fajardo and RHP Blake Aita

Grade: A

This was the major offensive splash of the offseason for Boston. Breslow utilized his pitching depth to send a young pitcher, Hunter Dobbins, who looked sharp in his first taste of the big leagues before he got injured for the season. Fajardo ended the 2025 season as Soxprospects’ Red Sox No. 10 prospect. Aita wasn’t in their top 30.

Contreras raked all season. Without him, the Red Sox would not have had any offensive power during the beginning of the season, and he was instrumental during the 32-5 stretch. It was a great piece of business by Breslow, who also got the Cardinals to pay down some of his contract. The only reason it wasn’t an A+ is that Contreras slowed down at the end of the season.

Red Sox acquire 3B Caleb Durbin, INF Andruw Monasterio and INF Anthony Seigler from the Brewers for LHP Kyle Harrison, INF David Hamilton and LHP Shane Drohan

Grade B

This was one of the most controversial moves Breslow made last offseason. He gave up on Harrison very quickly after he was the headline return of the Rafael Devers trade. He used him to acquire the replacement for Alex Bregman after they weren’t able to sign him to a long-term deal. Durbin’s abysmal start to the season and Harrison’s dominance quickly made this trade look like an F.

Durbin turned it around, though, and became a quality everyday player for the Sox. His toughness not only rallied the team, but also the fans, and he played Gold Glove defense at third base. Monasterio and Seigler both had stretches of being the guy during the season. Without them, the Sox may never have been able to make their incredible comeback. The three players they sent helped the Brewers to reach the World Series, but with without the players the acquired, the Red Sox season could’ve looked much different.

Red Sox acquire LHP Jake Bennett from the Nationals for RHP Luis Perales

Grade A+

When the Red Sox made this deal, fans were up in arms. Perales was a top five prospect in the system at the end of last season and he was traded away for a 25-year-old whose stuff wasn’t nearly as exciting. At the end of the season, it looks like a stroke of brilliance from Breslow.

Bennett was incredible as a rookie this season. Through his first nine starts, the lefty had a 2.35 ERA. While he slowed down as the season went on, he still finished with a 3.65 ERA in 113 innings. He had excellent command and was extremely good at limiting hard contact. He saved the Red Sox staff when the injury bug started to bite midseason. He is going to be a member of the Sox rotation for a while.

Red Sox acquire RHP Johan Oviedo, LHP Tyler Samaniego and C Adonys Guzman from the Pirates for OF Jhostnyxon Garcia and RHP Jesus Travieso

Grade D+

This trade has been sort of a lose-lose for both organizations. On the Sox side, Oviedo made one appearance before an injury cost him the season. He was a risk to take on, as he was still not stretched out after recovering from Tommy John surgery. The Red Sox only have one more year of team control on him.

Samaniego was solid in his MLB debut season, though he only made 20 appearances. He had a 2.66 ERA and didn’t allow a run to score in his first 11 appearances, but he just wasn’t in the majors long enough to make a difference. Guzman has slid into the 50s in SoxProspects top 60 for the Sox.

On the other side, the Password struggled through his 20-game stint with the Pirates, striking out 16 times and only walking once. Travieso was a top 30 prospect for the Red Sox at the end of last season; MLB Pipeline doesn’t have him in the Pirates’ top 30 anymore. Over one season, the best player in the deal has been Samaniego.

Red Sox acquire RHP Gage Ziehl from the Chicago White Sox for RHP Jordan Hicks and RHP David Sandlin

Grade C-

A year later, this trade really made no difference to the Red Sox season. Hicks had a fine season with the White Sox, posting a 3.94 ERA in 48 innings. It just wasn’t working with him and the Red Sox in 2025 and they needed to move him. Sandlin made his MLB debut for Chicago and had a 5.58 ERA in 40 innings. Sandlin may have factored into the Sox 2026 plans, but either as a back-end starter or reliever. Boston did have to send $8 million to Chicago to cover part of Hicks salary

Ziehl is a high-20s prospect for Boston. He is a starting pitcher who will likely factor in as a depth arm in 2027 after finishing the season in Triple-A. His potential sits as a back-end starter. It’s good they got value for Hicks, but Ziehl is nothing exceptional.

Red Sox acquire RHP Ryan Watson from the Athletics for INF Justin Reimer

Grade: C

Watson was a Rule 5 Draft choice by the Athletics that the Sox wanted. They sent Reimer, an infield prospect outside the top 30, to the A’s to acquire him. Watson was mostly the mop-up man in the pen for the Sox until they DFA’d him in August. He had stretches of being solid, but wasn’t ever trusted in any high-leverage spots.

Red Sox acquire OF Braiden Ward from Colorado for LHP Brennan Bernardino

Grade C+

While clearing out the 40-man roster at the Rule 5 deadline last winter, the Sox sent Bernardino to the Rockies. The lefty had been a workhorse in the ‘pen in his three seasons in Boston, and actually had a breakthrough year for the Rockies. In 74 appearances, the 34-year-old had a career-low 2.81 ERA. The Red Sox still had an elite bullpen without him, though.

Ward is an outfielder with incredible speed and base-stealing ability. He stole 61 bases in Triple-A this season, and there was a chance he could’ve broken into the playoff roster just because of his speed, without ever having played an MLB game. He is Rule 5 Draft eligible this offseason, so the Sox will need to add him to the 40-man roster this winter or risk losing him. Turning a veteran reliever into a potentially valuable piece is solid business on Breslow’s part.

Red Sox acquire C Ronny Hernandez from White Sox for LHP Chris Murphy

Grade C

Another trade Breslow made to clear the 40-man roster: Murphy had a solid 2025 season with the Red Sox, but was not a high-leverage arm. He struggled in Chicago this season with an ERA near five. Ronny Hernandez is a depth catcher. Last offseason, Breslow acquired multiple catchers to build depth in the organization, and Hernandez was one. He spent the entire 2026 season in High-A, where he did have a .955 OPS in 67 games.

Red Sox acquire C Luke Heyman from the Mariners for RHP Alex Hoppe

Grade: B-

Instead of protecting Hoppe from the Rule 5 Draft, the Sox dealt him to Seattle. The Red Sox got Heyman in return, who has climbed up the Red Sox prospect rankings into the top 30. Instead of potentially losing a player for nothing, they turned him into something valuable: a solid trade.

Red Sox acquire OF Isaiah Jackson from the Angels for INF Vaughn Grissom

Grade: B-

The Red Sox finally gave up on the player they acquired for Chris Sale. He was out of minor league options heading into the season, so the options were to keep him in the majors, DFA him or trade him. They sent him to L.A. and got back a prospect who has also climbed into the Sox top 30 in Jackson. Grissom was fine for the Angels, an OPS under .700, but did have 13 home runs and 72 RBIs. He wasn’t going to play in Boston, and this grade is purely based on what happened since the trade, so it’s not too bad.

Red Sox acquire Tristan Gray from the Rays for Luis Guerrero

Grade: N/A

Another instance of clearing the 40-man roster, the Sox dealt Guerrero to the Rays. Guerrero never got a real shot with the Red Sox, making 22 appearances over two seasons. He spent the season in the minors for Tampa. Boston traded Gray away two months later.

Red Sox acquire C Nate Baez from the Twins for INF Tristan Gray

Grade: C+

Another instance of the Red Sox needing a depth catcher. Baez spent most of the season in Portland and got 15 games in Worcester. Across the two levels, he hit .223 with an OPS in the 600s. Gray played 66 games for the Twins and had a -0.7 bWAR. The reason this is a C+ is that they acquired Gray earlier in the winter, realized they couldn’t use him because he was out of minor league options, and were still able to trade him for something.

Overall Grade: B+

For trade deals alone, Breslow did an excellent job. Only one trade was truly a negative, and even then it provided some value. Breslow was able to make multiple key additions to the roster via trades while utilizing the Red Sox organizational depth. The Red Sox are going to need Breslow to do this again this winter, as they have no real space for free agents headed into the offseason.

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