Craig Breslow was hired as the Boston Red Sox Chief Baseball Officer Oct. 25, 2023. Throughout Breslow’s tenure, the Red Sox have posted a 170-154 regular season record as well as a 1-2 record in the postseason. Boston finished third in the American League East in each of the baseball boss’s first two seasons, failing to make the playoffs in his first.
Breslow does not control his budget, his ownership’s drive to win, and nor should he be judged based on those factors. Red Sox fans are — justifiably — frustrated by the team’s lack of an appetite to spend or commit long term money to proven talent.
Boston entered 2026 outside of the MLB’s top ten list of cash spending, while the last time they won the World Series in 2018, they ranked first. Before that, in 2013, they were third. So say you believe when the organization tells you that they’re championship driven; say you believe when Tom Werner said they’d go “full throttle” in the 2023-24 offseason. If the Red Sox and Fenway Sports Group’s main objective is to win championships, one thing for sure is they’re following a different model than the one that delivered four World Series titles to the franchise.
“They have gone from the top of baseball to the middle, mostly by eliminating what we like to call the megadeal — the long-term, $200+ million contracts awarded to star players,” said Tony Massarotti of 98.5 The Sports Hub.
The Red Sox are no longer managing themselves as a baseball giant, despite the market they are in, and the resources they have. Instead, their approach has been more like a mid-market franchise trying to build a team in the aggregate, rather than with a big check.
So, if that’s the model, we can’t blame Craig Breslow for not being in on Juan Soto — at least seriously interested — on any contract of his sorts. Breslow isn’t here to do that, he’s here because of his eye for talent. He, with his Ivy League background, is here to modernize the Red Sox through analytics and reshape the franchise into a sustainable contender.
If you disagree with that approach — too bad. You’re welcome to chant “sell the team” from your pricey Fenway Park seat, which is ranked the second highest average price in the MLB, but that’s not going to change anything. Just ask John Henry’s sly smirk and scoff after hearing said chants.
The direction, philosophy and financials are one that appear to be succinct with Craig Breslow’s thinking. But it isn’t his fault that Fenway Sports Group is employing them. Breslow can be judged through the moves he’s made and how good a job he has done working within his constraints. His trades and free agency acquisitions.
Breslow’s first notable deal came in 2023 when he dealt former CY Young winner and World Series Champion Chris Sale to the Atlanta Braves for infielder Vaughn Grissom. Grissom never caught on in Boston, playing in just 31 games with the big league club while spending most of his time in Worcester before being traded to the Los Angeles Angels for a minor league player. Meanwhile, Chris Sale shoved in his first two years with the Braves, posting a sub three ERA in each and eventually is being re-signed.
Arguably his biggest win for the Red Sox was trading for pitcher Garrett Crochet from the Chicago White Sox. Boston sent four prospects — including touted names like Kyle Teel and Braden Montgomery — and found themselves with a bonafide ace who was extended months after the deal.
Breslow’s biggest splash was the Rafael Devers deal. This one is often blamed on ownership, and it’s credible. The Red Sox gave Devers a contract they never wanted to pay and subsequently bailed out of it. San Francisco took on the whole contract, and in exchange got a discount on what they had to send back to Boston. The Red Sox received Jordan Hicks, Kyle Harrison, Jose Bello, and James Tibbs III —who had been San Francisco’s most recent first round pick. Hicks was one of the worst relievers in the league during his time in Boston, and is no longer with the team. Jose Bello is still pitching in the Red Sox minor leagues. Kyle Harrison, I’ll get to later, and James Tibbs III is thriving in the Los Angeles Dodgers minor league affiliates and looks like a top prospect after being dealt at last year’s deadline for Dustin May.
Dustin May had a 5.40 ERA for Boston and did not appear on the postseason roster that year. He was let go following the end of the season.
Kyle Harrison, who seemed like the last piece of the return from the Giants that received Boston’s former franchise player, was dealt this offseason to the Milwaukee Brewers in a package deal. The Brewers got Harrison, another pitching prospect in Shane Drohan, utility player David Hamilton, while Boston received Caleb Durbin, Andruw Monasterio and Anthony Siegler. This deal was essentially made for Caleb Durbin to be Boston’s new third basemen after moving off both Rafael Devers — former All-Star, World Series Champion, and a 313.5 million dollar contract — and Alex Bregman, also a former All-Star, World Series Champion, with a hefty number to his name. Caleb Durbin is being paid under one million dollars to play for the Red Sox this season on a rookie deal — a budget friendly contract. The main exchange here was Harrison for Durbin. Harrison has a solid 3.07 ERA in three starts for the Brewers showing good stuff. Durbin is hitting a putrid .106 so far for Boston with double the amount of strikeouts to walks. Not a great start for Breslow’s new corner infielder.
Breslow doesn’t seem to be capable of building in the aggregate for the Red Sox, his prospects for a majority have failed, and the ones he’s let go have succeeded. What’s interesting is that his two best moves have been far more aggressive and financially demanding than the rest. His Crochet deal has paid off with dividends, and taking on Willson Contreras’ 87.5 million dollar contract in a trade with St. Louis looks great early on in 2026.
Where the Red Sox have succeeded themselves is in situations where they actually extend themselves to make a deal work, rather than giving up on some value in return for financial sustainability.
It’s abundantly clear what works and what doesn’t for the Red Sox. Craig Breslow is not capable of building a real contending team through the aggregate. He doesn’t have the eye for talent, and he doesn’t have the backbone to stand up to ownership. Until the Red Sox realize their business model is exactly that and not a drive to win, they will continue to middle the league just as the other middle-market teams do.
