The Boston Red Sox were one of the finest and proudest organizations in baseball up until the last five seasons, excluding the magical 2021 season. Even in these past six seasons, there weren't any true head-scratchers when hiring executives to run their baseball operations, including Chaim Bloom and Craig Breslow, where ownership's vision was to compete whilst cutting their payroll in the process.
When they hired Bloom, everyone knew (for the most part) what to expect; he had previously worked with one of baseball's lowest payrolls, the Tampa Bay Rays, yet knew how to scout and bring in players who were DFA'd or released by their respective teams. But he didn't know how to negotiate with ownership, and one source said that, unlike Dave Dombrowski, he wouldn't stand up to Sam Kennedy or John Henry to demand the signing or trading for star players. When he had an idea and they didn't think it was financially viable, Bloom would shut that idea down altogether.
As for Breslow, he's been able to stand up, but in a rather stubborn approach. Having his own circle of trust, regardless of whether they support him fully or not, is Exhibit A on the hard drive. He also focuses aggressively on analytics, which is why many within the organization are out of his circle of trust, and there are only a select few whom he picked to stay in the loop.
Craig Breslow has the eye for pitching talent
Nobody truly knows what Breslow is thinking, but his actions have shown that he knows pitching when he sees it. As a former pitcher himself, who won with the organization back in 2013, he's drafted the likes of Payton Tolle, Kyson Witherspoon, Anthony Eyanson, and Marcus Phillips over his only two drafts with the ballclub. Not only that, but he's wisely brought in key contributors like Aroldis Chapman, Justin Slaten, Tyler Samaniego, Garrett Crochet, Justin Wilson, Lucas Giolito, and Sonny Gray.
The Red Sox's 2026 pitching staff is top 10 in baseball, currently in 9th place with a combined 3.87 ERA.
But, there are many moves that have baffled the fans and people/players within the organization...
But he continues to make head-scratching decisions
The Rafael Devers trade was a disaster
First came the Rafael Devers trade. After poorly communicating, whilst also being aggressive, the signing of star third baseman Alex Bregman, their franchise third baseman, Rafael Devers, took it as a huge surprise. Thinking he was the starting third baseman until the end of his contract extension, which he signed back in 2023 for 11 years, $333 million, turned out to be a ruse. His replacement was brought in without his hearing about it, and he was not a fan of that.
This, along with trying to move him to first base after the Triston Casas season-ending injury in early May, which he refused, built an irreparable relationship between their best hitter and the Red Sox front office. Devers' distrust of the organization to do the right thing caused tension between him and Craig Breslow, and Breslow ended up trading him in a shocking blockbuster on Father's Day, June 15th, 2025.
Devers, the best player the franchise had had since Mookie Betts, was sent off to the San Francisco Giants for four players: LHP Kyle Harrison, RHP Jose Bello, OF James Tibbs III, and RHP Jordan Hicks. Mind you, three out of the four players acquired in this trade (Harrison, Tibbs, and Hicks) were also traded away to other teams by Spring Training this season.
Afterwards, not only has Devers been willing to play first base for the Giants, but Bregman, who signed a three-year deal with one of his two opt-outs after his first season, opted out of his contract. While the Red Sox were favorites to sign him, the Chicago Cubs poached him after they revealed they were willing to add a no-trade clause, which the Red Sox refused to do.
"Forging" the offense
One of Breslow's biggest weaknesses, besides his communication standards, is creating an offensive threat in that Red Sox lineup.
Just this past offseason, Breslow had four great opportunities to acquire a big bat, whether that was in free agency or by trade. When the 2025 Winter Meetings came around, the rumors were swirling heavily about Ketel Marte being traded to the Red Sox. However, the Red Sox, even after offering Franklin Arias and Payton Tolle, among other prospects in negotiations, backed off when the Arizona Diamondbacks GM Mike Hazen wanted top prospect Marcelo Mayer as well. Whether this was because he wasn't seeing Trevor Story as one to repeat his amazing bounce-back season in 2025 or not is a different story, but it would make sense. But regardless, Marte is still miles better than any of their current infielders right now.
Power hitters Pete Alonso and Japanese import Kazuma Okamoto were available in free agency, and the Red Sox were in talks with both hitters for contracts. However, the first domino to fall off the hook was Alonso. His wife, Haley, grew up in Quincy, so with her family there, it would've been easier for everyone. But they were sadly outbid by the Baltimore Orioles.
They ended up signing the All-Star slugging first baseman to a five-year, $155 million deal. Essentially making $31 million a season, the Red Sox weren't willing to pay that much for him. They were outbid by a heavy amount, only offering three years, worth $85 million ($28M AAV), and an option for a 4th year, worth $35 million that season. This was a lowball from many perspectives, mainly towards Alonso and his agent, Scott Boras.
Okamoto, along with Alonso, was also interested in signing with the Red Sox. It was either them, the Pittsburgh Pirates, or the Toronto Blue Jays. Negotiations never gained traction, and he ended up signing with the Blue Jays for a mere four-year, $60 million deal, which was more than affordable for them.
Speaking of the Blue Jays, their franchise shortstop, Bo Bichette, was hitting the open market as well. In the Winter Meetings, the Red Sox were very interested in him, including having a Zoom Meeting that Bichette was very impressed by afterwards.
But when negotiations started, things fell apart quickly. Bichette fell into the $300 million range, and Breslow pulled out of talks entirely, officially pivoting to upgrading the pitching staff. He did so by signing Ranger Suarez to a five-year, $130 million deal. Bichette ended up signing with the New York Mets for three years, worth only $126 million.
While Breslow tried to acquire a right-handed bat, he only came back with Caleb Durbin, who had a very rough start with the team through May, batting only .183 on the season. Meanwhile, the players he sent to the Milwaukee Brewers in that trade were the aforementioned Kyle Harrison, David Hamilton, and prospect Shane Drohan, who are all key contributors to that 2026 Brew Crew team. Harrison, in particular, has turned into a bonified one-two punch alongside Jacob Misiorowski, posting a 2.72 ERA with 77 strikeouts in just 59 2/3 innings pitched.
Craig Breslow's time in Boston should be coming to an end
Absolutely nothing is going Breslow's way, even if it did work out last year. The Devers trade has come back to bite him in the worst ways, especially with Tibbs and Harrison performing well on their new teams. Not acquiring a right-handed power bat has cost them dearly, being dead last in the MLB in home runs with only 49 on the season as of June 8th.
He fired Alex Cora in mid-May, the World Series-winning manager for the Red Sox back in 2018, alongside most of the hitting department (hitting coach Peter Fatse, along with three other assistant hitting coaches/coordinators). Many believe it was Breslow trying to pass the blame onto Cora, even though Cora had his own flaws as a manager that cost them games in the past, but it can pass off as a believable rumor.
Many within the organization are furious at the results, with former GM and now part-owner of Fenway Sports Group, Theo Epstein, being disappointed in Breslow's work. John Henry is also reportedly "worried" about this season going down the wrong path.
This has gotten so bad that ownership has decided to step in and get involved in trade talks for said right-handed power bats. They're even willing to take on a bad contract in a desperate time.
”Today I talked to someone with another team that told me that it’s to the degree that the Red Sox ownership has gotten involved. I have not confirmed the name of the owner… but an owner, one of the Red Sox ownership group, is actually calling around and trying to grease the skids to something to add a right-handed bat," Buster Olney said on WEEI's 'Rich and Ken With Ted Johnson.'
As for Breslow himself, his job is surely on the line, even if ownership hasn't considered firing him. But timing is everything. If Breslow and the Red Sox don't get a right-handed bat by August 4th, John Henry will leave no stone left unturned and get the axe immediately. But since Breslow's contract expires after this year, it's hard to believe they'll fire him in the middle of the season and cut their losses, especially with the lockout coming after this season.
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