This was a pretty active offseason for Red Sox chief baseball officer Craig Breslow, who swung 13 trades while making a handful of notable free agent signings.
With the season now at its unofficial halfway point, how have those moves worked out for the Red Sox so far? Here’s a breakdown of the most significant moves, plus one notable move that wasn’t made.
Caleb Durbin trade
(Red Sox acquire INFs Caleb Durbin, Andruw Monasterio and Anthony Seigler plus Competitive Balance B draft pick No. 67 overall, OF Owen Hull from Milwaukee Brewers in exchange for LHPs Kyle Harrison and Shane Drohan and INF David Hamilton)
For the first few months this trade was shaping up to be a disaster. Durbin got off to a terrible start, Monasterio was a serviceable bench player but nothing more and Seigler spent most of the first half either injured or in Triple-A. Meanwhile, Harrison broke out as an early National League Cy Young Award contender, and Drohan emerged as a key contributor for Milwaukee’s pitching staff as well.
Now, it’s looking more like a possible win for both sides.
Durbin has caught fire and played a key role in Boston’s recent turnaround, and he now ranks fifth on the team with 2.2 Wins Above Replacement on the season. Seigler has also provided the Red Sox with a spark, and lately he’s settled in as the club’s everyday second baseman and leadoff hitter.
Harrison, meanwhile, has come back down to Earth. After posting a 1.57 ERA in 57 1/3 innings over his first 11 starts, he has since posted a 6.15 ERA over 26 1/3 innings in his last six. Drohan has a 3.09 ERA on the season and has pitched well since moving to Milwaukee’s rotation in early June, and David Hamilton has 18 stolen bases in 74 games but is currently on the injured list.
Sonny Gray trade
(Red Sox acquire RHP Sonny Gray from St. Louis Cardinals in exchange for RHP Richard Fitts, LHP Brandon Clarke and RHP Patrick Galle)
This deal has been a huge win for the Red Sox so far. Gray was arguably MLB’s biggest All-Star snub after going 11-1 with a 2.54 ERA over 95 2/3 innings in 17 first-half starts. He has been an invaluable contributor and helped the Red Sox overcome the extended loss of Garrett Crochet to injury.
The Cardinals won’t get much out of the players they acquired, at least not this year. Fitts underwent lat surgery in mid-April and will miss the entire season, and Clarke, who Baseball America ranks as the Cardinals’ No. 12 prospect, missed the first half after undergoing surgery to address an aneurysm in his left arm. Clarke just recently returned to the mound and made his 2026 debut in a rookie ball game this past Saturday.
Galle, originally a player to be named later, has posted a 7.62 ERA in 22 relief appearances for St. Louis’ High-A affiliate.
Willson Contreras trade
(Red Sox acquire 1B Willson Contreras from St. Louis Cardinals in exchange for RHPs Hunter Dobbins, Yhoiker Fajardo and Blake Aita)
Another home run for the Red Sox. Contreras has been spectacular ever since his arrival and has been by far the club’s most consistent and productive offensive contributor. Contreras earned his fourth All-Star selection after batting .285 with 20 home runs and a .921 OPS, all of which are on pace to be new career highs.
Dobbins bounced back and forth between the majors and minors and currently has a 4.03 ERA in five MLB appearances. Fajardo ranks as St. Louis’ No. 5 prospect and has 86 strikeouts in 63 2/3 innings in High-A, and Aita was recently promoted to Double-A after posting a 3.92 ERA in 14 High-A starts.
Ranger Suarez signing
(Red Sox sign free agent LHP Ranger Suarez on five-year, $130 million deal)
So far Suarez has lived up to his hefty price tag as a front-of-the-rotation difference-maker. The left-hander earned his second career All-Star selection after posting a 3.15 ERA with 97 strikeouts in 91 1/3 innings over his first 17 starts. Suarez is currently on the injured list with a left groin strain but the injury isn’t expected to sideline him for long.
Failure to re-sign Alex Bregman
(Chicago Cubs sign free agent 3B Alex Bregman on five-year, $175 million deal)
The biggest non-move of the offseason was the club’s failure to bring back third baseman Alex Bregman in free agency, with the veteran ultimately opting to take a more lucrative offer from the Cubs.
Losing Bregman’s bat and leadership was felt immediately when the Red Sox struggled out of the gate, but overall the 32-year-old has been a roughly league average performer this season. Entering the All-Star break, Bregman was batting .241 with nine home runs, 41 RBI and a .696 OPS. His 96 OPS+, which equates to 4% worse than league average offensive production, is also the lowest of his career.
His 2.3 WAR still ranks fourth on the Cubs, who are 54-42 and second in the National League Central.
Johan Oviedo trade
(Red Sox acquire RHP Johan Oviedo, LHP Tyler Samaniego and C Adonys Guzman from Pittsburgh Pirates in exchange for OF Jhostynxon Garcia and RHP Jesus Travieso)
Originally expected to be a top contender for the club’s last starting rotation spot, Oviedo only made one appearance for the Red Sox out of the bullpen before going on the injured list with a right elbow flexor strain. He began a throwing program in June but still isn’t considered close to a return.
Samaniego has been a positive contributor to the Red Sox bullpen, posting a 2.66 ERA in 20 outings, including 13 consecutive scoreless appearances to start his MLB career, but has bounced back and forth between Boston and Worcester.
Garcia, who Baseball America ranks as Pittsburgh’s No. 7 prospect, has spent most of the season in Triple-A and batted .200 with only one extra-base hit in 13 MLB games.
Jake Bennett trade
(Red Sox acquire RHP Jake Bennett from Washington Nationals in exchange for RHP Luis Perales)
Time will tell which team ultimately wins this trade, but Bennett has certainly been the bigger contributor of the two pitching prospects so far.
Since making his MLB debut on May 1 the left-hander has made eight big league starts and posted a 2.64 ERA with an impressive 0.944 Walks and Hits Per Innings Pitched (WHIP). He’s seemingly gotten better as the season’s gone along too, posting four consecutive quality starts to finish the first half.
Perales has yet to make his MLB debut but has posted a 3.78 ERA with 59 strikeouts in 69 innings over 17 outings at Triple-A.
