The Craig Breslow era in Boston has felt like a roller coaster ride. Hired at the start of the 2023-24 offseason, the Boston Red Sox have not had a losing season under Breslow, despite wild swings in the team's form over the three years.
With the Red Sox clinching a playoff berth for the second year in a row, team ownership decided that now was the time to exercise two options on their Chief Baseball Officer's contract, guaranteeing his deal for the 2029 and 2030 seasons. On the surface, a head of baseball operations who got his team to the playoffs in years two and three of their time running the club getting years added to their contract, would make sense, but in Breslow's case it isn't as straightforward.
It was only three months ago when most of Red Sox Nation was calling for Breslow's head. The Red Sox were 32-46 on June 24, dead last in the division, and it already seemed like the season was over. It took a miraculous turnaround to get the team to the playoffs. Not to say that Breslow had nothing to do with that; he had added a lot of players to the roster who were key contributors, but that has a lot more to do with the players and coaches than the front office.
Breslow's tenure has also been marred by controversy, specifically the Rafael Devers drama. It was his handling of the situation, along with former manager Alex Cora, that ultimately led to the fracture of the relationship with the team's then-face of the franchise. While the fanbase was split on whose side they took, player or team, his actions after the fact didn't make it any better.
Red Sox's Craig Breslow had the hottest seat of any GM only three months ago
It was the signing of Alex Bregman that caused the Devers drama in the first place. While Breslow was praised for the signing, Bregman opted out at the end of the year and was then not re-signed. The Red Sox went from two elite third basemen to none in the span of a season. It wasn't a good look for the Red Sox CBO.
Now, Breslow's pivot from all of the drama and mess surrounding Devers and Bregman looks incredibly good in hindsight. The additions of Ranger Suarez, Sonny Gray, Willson Contreras, Caleb Durbin, and others have been extremely impactful to the Red Sox's success this season. While some of those moves were celebrated at the time they happened, others like the Durbin-Kyle Harrison swap (that also netted the Red Sox Andruw Monasterio and Anthony Seigler) were heavily scrutinized.
Breslow also made good moves at the trade deadline, adding Erik Miller and Eli White, who have looked good for the Sox. He also made the splash trade for Adley Rutschman, which hasn't worked as well on the field, but certainly instilled confidence in the team, knowing the front office believed in them.
Red Sox could've softened the impact by extending one of Craig Breslow's options at first
All of this is to say that Breslow's time as CBO hasn't been as smooth sailing as the records would suggest. He has had some high highs but also some low lows. Why did ownership feel the need to exercise both options right now? The first option wasn't needed until the 2029 season, two years out. The second was for 2030, three years out.
Doing the first one now would've been fine — picking up the 2029 option gives Breslow another three comfortable seasons on his contract. That would make him more comfortable making moves for the future and give him the job security to know he will likely be in place to see them play out. Selecting the 2030 option on the same day was unnecessary, though.
There have been too many hiccups in the three years under Breslow to say he has warranted another four seasons. The start of 2026 could easily repeat itself in 2027. Should ownership feel the need to relieve him of his duties early, then this makes it that much harder. Breslow hasn't won a World Series in Boston; in fact, he hasn't even made it out of the Wild Card round. Exercising the option for 2030 feels very premature.
Breslow has not done a bad job in Boston. At the end of the day, it's results that matter, and Breslow's teams have made the playoffs two out of three times. He shouldn't be fearing for his job, but his contract also wasn't ending for another two seasons. It feels early to be handing him the keys so far down the road after the drama of his first two years as CBO.
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