The Boston Red Sox have been careful, rational, and frugal so far this offseason, which are often beneficial virtues in the game of life. The problem for Boston's chief baseball officer Craig Breslow is that none of those three qualities are beneficial when it comes to building a big-market team in the game of baseball.
While the Toronto Blue Jays and Baltimore Orioles have been appropriately loose with their wallets this transaction cycle, the Red Sox have been hiding in the corner of the party. Unless Breslow's about to announce himself at said party by jumping on top of the counter, smashing some bottles, and signing Bo Bichette and Framber Valdez in one fell swoop, this has been a very confusing six weeks.
The Red Sox are a gigantic market mega-power that's traditionally high-rolled with the game's richest clubs in free agency. Why is Breslow acting like he's the GM of the Colorado Rockies? It should be said that Boston and Colorado are the only MLB teams that have not signed a free agent this offseason.
Fans, pundits, and the rest of the world have no idea why the Red Sox are being so cautious
It's not just Red Sox fans that are shaking or scratching their heads at Boston's thriftiness these days. ESPN's top MLB insider Jeff Passan dug into the Sox during a recent episode of Buster Olney's Baseball Tonight pod. Responding to reports that the Red Sox weren't willing to compete financially for Pete Alonso and Kyle Schwarber, Passan criticized Breslow and Co. for being too rational.
“We’ve seen the Red Sox in recent years, they try to operate rationally," Passan said. "Operating rationally, generally speaking, will not get you free agents. It is an irrational market, and sometimes you got to get a little irrational.”
Craig Breslow when it’s time to sign free agents https://t.co/S1F9lJWRbd pic.twitter.com/BSXNPJDKwu
— Liam Fennessy (@LiamFennessy_) December 18, 2025
Boston's tight-fisted offseason has been contextualized by some troubling reports. MassLive's Sean McAdam cited an anonymous MLB agent who said that the Red Sox are essentially no longer interested in long-term contracts for players over the age of 30. But that's when many players' first contracts expire.
To take the stance that you're not interested in long-term deals — especially if you're a big-market club — is not only unfair to fans but flat out pretentious. It gives off the vibe that you think you're above the rules of the game. Long-term contracts are simply an unavoidable aspect of building a championship club. Face the music on that one, or become the White Sox and Pirates of the world. Even Pittsburgh made a ceremonial offer to Schwarber earlier this month.
Then again, this is how the Red Sox have been operating so far this offseason — as a small market franchise. The Sonny Gray trade would have been lauded as a really strong move for, say, the Washington Nationals, but Boston fans reacted to the trade by asking, "Is that it?" And with good reason. The Red Sox are on the verge of real contention. Marginal moves aren't going to get you to that next level.
Report: Red Sox in late round talks to acquire heavily discounted, used pitching machine on eBay pic.twitter.com/tgTqKx5ve2
— Boston Globe Pitchbot (@BostonSatire) December 16, 2025
Speaking of marginal moves, the only news Red Sox fans have to digest recently is Breslow trading a wildly talented, young pitcher (Luis Perales) for a less-heralded, though intriguing arm with upside (Jake Bennett). Hearing The Boston Globe's Alex Speier described the trade, though, it certainly comes with a lot of "ifs."
"Based on his size, the Sox believe Bennett can add power to his arsenal once on a structured velocity program like the one that yielded sizable gains with Payton Tolle and Connelly Early," Speier wrote. "If Bennett can add power, and if he can refine the shapes of his evolving secondary pitches, Bennett could emerge as a No. 4 or even No. 3 starter — not quite the ceiling of Perales, but close enough that the Sox were drawn to his more solid floor."
It's mid-December, and Red Sox Nation is debating the ceiling and floor of two guys who haven't impacted MLB. Meanwhile, Alex Bregman remains unsigned, and Boston's roster looks markedly worse than last year's at the moment. Breslow has either overcomplicated this entire offseason into oblivion, or the best is yet to come.
