Craig Breslow, the current Chief Baseball Officer of the Boston Red Sox, and his predecessor, Chaim Bloom, have repeatedly come under fire for decisions they have made while at the helm of the club. And, to be sure, many of those decisions deserve scrutiny.
However, there are a handful of moves (or non-moves) that have proven to be quite fruitful. Unfortunately for the two leaders, those get forgotten or overlooked.
Xander Bogaerts
When Bloom was at the helm, in 2022, he offered franchise stalwart Xander Bogaerts a six-year contract worth $162 million. That would have taken the shortstop through his age-35 season. The San Diego Padres swooped in and offered the pride of Aruba an 11-year deal worth $280 million. There was simply no reason to try to match that; and Bogaerts would have been a fool not to accept it. Red Sox fans were sad to lose the four-time All-Star and two-time world champion, but it was smart business. And it should be noted that Bogaerts has not had an OPS above .800 since joining the Padres, and this year has a 77 OPS+ (meaning he is 23% below average).
Rafael Devers
After losing Mookie Betts to the Dodgers and not signing Bogaerts, Bloom needed to make a splash – for the team and for the fanbase. So he signed third baseman Rafael Devers to an 11-year, $313.5 million contract in 2023. Devers performed at a level befitting a nearly $30-million player, posting an OPS+ of 126 in 2023 and 142 in 2024. In the first half of 2025, he was hitting just fine (.905 OPS, 152 OPS+). But his attitude didn’t match his bat. He refused to move to first base when the team signed Alex Bregman, and then just barely agreed to become the everyday designated hitter. In June of last year, Breslow thought he could improve the team – especially the clubhouse – if he sent Devers away. So off to San Francisco he went.
In return for Devers, the Red Sox received pitchers Kyle Harrison and Jordan Hicks and outfield prospect James Tibbs III. Regardless of what they got back, Boston relieved itself of approximately $250 million in obligations owed to a disgruntled player through 2033.
Devers slashed .236/.347/.460 in 90 games with the Giants last season. This year – on the basis of a hot month – he is now slashing .247/.319/.475 with 22 homers.
New Infielders
Boston traded Harrison (along with infielder David Hamilton and pitcher Shane Drohan) to Milwaukee in return for infielders Caleb Durbin, Andruw Monasterio, and Anthony Seigler, plus a draft pick. As of this writing, Durbin is slashing .246/.313/.399 with 10 home runs. That is not exactly the same as Devers, but if you squint, it looks pretty close for $28 million less. Monasterio has filled in nicely for the BoSox – he hit the game-winning home run in Sacramento earlier this week – and currently has a 119 OPS+. Seigler didn’t expect to get much playing time with Trevor Story and Marcelo Mayer on the roster, but both have been out most of the season with injuries, so Seigler has gotten 113 at bats and put up a 105 OPS+. These stats don’t jump off the page and these names don’t put butts in the seats, but they do help win games, which is ultimately what this is all about.
Breslow did appear to have some egg on his face at the beginning of the season, as Harrison thrust himself into the Cy Young conversation with an 8-2 record and a 3.01 ERA for Milwaukee. However, the pitcher has been out since early July with forearm and elbow tightness. Without any setbacks, he could be back in the Brewers rotation sometime in August. But, as the recent trade of Connelly Early to the Nationals shows, the Red Sox don’t lack for pitching depth. What they needed was players to fill holes on the infield, and Durbin, Monasterio, and Seigler have done just that.
Sonny Gray
Prior to the Thanksgiving break, Breslow sent three pitching prospects to St. Louis in return for veteran righty Sonny Gray. The Cardinals also threw in $20 million, meaning the Red Sox are only paying the pitcher $15 million for a league-leading 13 wins, a 2.94 ERA, and a 138 ERA+.
Jake Bennett
In a little-noticed move two weeks before Christmas, Breslow swapped right-handed pitching prospect Luis Perales to Washington for left-hander Jake Bennett. Bennett has provided some of the aforementioned pitching depth. In 11 starts this year, he has a 2.74 ERA, a WHIP below one, a 4-to-1 K/BB ratio, and a 148 ERA+.
Willson Contreras
‘Twas the days before Christmas, and Breslow sent MLB pitcher Hunter Dobbins and two minor league pitching prospects to the Cardinals in return for first baseman Willson Contreras. Contreras has become the heart and soul of the 2026 squad, both on and off the field. And it doesn’t hurt that he also leads the teams in home runs (23), RBI (67), and OPS+ (166).
Craig Breslow
After sending Early to Washington in return for slugging infielder Curtis Mead*, Breslow told the collected press: “I’ve tried to shift to our goal not to win the trade. Our goal is to make our major league team better. Sometimes, the most straightforward way to do that is a need-for-need-type trade.”
*Mead struck out in his first at bat for the Red Sox, then got hit on the wrist in his second. He is now on the IL with a fracture that will keep him out of the lineup for at least six weeks.
With the trade deadline just two days away, it will be interesting to see how many moves Breslow is able to make to further improve the team, even if he “loses” the trade. There is no doubt that Red Sox Nation will be watching closely.
