Key Points
Bullet point summary by AI
- A key decision-maker faces mounting pressure as the trade deadline approaches for one struggling MLB franchise.
- His past deadline moves have drawn widespread criticism and created skepticism about his current strategy.
- The next few weeks will test whether this leader can adapt or risk further consequences for the team's future.
After Jared Carrabis of the Section 10 Podcast alluded to the notion that the Boston Red Sox could fire Chief Baseball Officer Craig Breslow before the Aug. 3 MLB trade deadline, there was a fervor in the fan base about what could transpire. However, at least someone appears to be giving Breslow a vote of confidence in response. That comes after Tim Healy of the Boston Globe reported that the Red Sox have no plans of firing Breslow, nor has it even been discussed at this point.
With a loss in Tampa on Monday night, the Red Sox fell to 27-37 on the season, 10 games below .500. They have woefully underperformed, especially with two of their biggest stars, Garrett Crochet and Roman Anthony, sidelined for the past month-plus and for longer to come. Boston checks boxes across the board as a seller, but it also appears that Breslow is intent on making this roster work, which could mean doubling down on the investment at the trade deadline.
The Red Sox giving the trade deadline keys to Craig Breslow is dangerous
A reasonable, rational man would look at the trade deadline and see what the best course of action for the Red Sox is. Trade Aroldis Chapman as one of the most valuable relievers on the market. Trade Willson Contreras as an impact bat. Consider moving Sonny Gray, Jarren Duran and Connor Wong depending on the league-wide interest. And in turn, Boston can stockpile pieces to build around a young core that's still enticing for the future with Anthony, Crochet, Payton Tolle, Ranger Suarez, Connelly Early, Ceddanne Rafaela and Wilyer Abreu.
But there's a real chance that Craig Breslow will not be operating like a reasonable, rational man given the position that he's currently in.
Whether Red Sox ownership has discussed firing Breslow explicitly is, frankly, irrelevant — and, it should be noted, can only be trusted but so much given the timing of the reporting and the subsequent subtext. With how poorly so many of Breslow's biggest moves and moments have aged since he was hired to be at the head of Boston's front office, his seat is hot and the pressure is turned up.
Doing my best Sean Bean impression, one does not simply trade Rafael Devers and fire Alex Cora without repurcussions. Those two landmark decisions for this organization put the red dot squarely on Breslow in terms of who to blame if things don't improve and if the roster he built isn't a winner. And again, this is a team currently 10 games under .500 — they certainly don't look the part of a winner at this juncture.
If Breslow is determined to prove that it is, though, that changes the math for the Red Sox at the trade deadline because of who's making the calls. They're going to buy, and that will cost assets to do so, while also likely mortgaging some other potential assets by not trading away the aforementioned veterans. It's difficult to call it going all-in, but it's something akin to that in a way.
And what makes that even riskier and more harrowing is Breslow's history at the deadline in Boston.
Craig Breslow has been a trade deadline dunce in Boston
Calling Breslow an abject failure in his two trade deadline performances to this point wouldn't be remotely hyperbolic. You can start with the Devers trade, made about this time last season, and how disastrous that was. The return netted the Red Sox Kyle Harrison, Jordan Hicks, James Tibbs III and Jose Bello. Harrison was traded in another lost deal to Milwaukee, Hicks was DFA'd, and Tibbs was traded for two months of terrible pitching from Dustin May.
But it goes deeper than that. At the 2024 trade deadline, the Red Sox needed bullpen help and desperately needed an impact right-handed bat. Breslow added Lucas Sims and Luis Garcia, both of whom were duds once they arrived in Boston, while adding only Danny Jansen offensively. He also, for some reason, also traded for James Paxton and Quinn Priester, the latter of whom was sent to Milwaukee as well.
It didn't get better at the 2025 deadline, either. The starting pitching upgrade that they needed ended up being May, who was nothing short of a disaster. Meanwhile, the other notable move was adding Steven Matz, who was fine, but also not a needle-mover in any sense of the word. More notable was Breslow reportedly not being able to get a Joe Ryan trade across the finish line, which has been a theme for his tenure in a number of rumored trade negotiations.
This is the guy that's now likely going to be working against the grain of what the Red Sox should do at the trade deadline, buying to try and take advantage of a weak American League despite an inherently flawed roster. When you consider that through the lens of Breslow not getting deals across the finish line, it sets Boston up for a situation where a desperate decision-maker could overpay to get guys that fit his model. It also means the possibility of risking future success in the hope of more immediate returns.
The one silver lining with Craig Breslow running the Red Sox trade deadline
As an optimist by nature, I'm going to find something positive that we could hopefully see as a result of this. The simple truth is that the Red Sox are essentially putting Craig Breslow's long-term fate with the organization in his own hands. It's going to be a situation where he'll benefit from his successes and pay for his failures.
Even if you're ardently against Breslow running Boston's operations, if this is the wake-up call that he needs for the Red Sox to operate like the Red Sox and make moves that will help this team compete, then that achieves the goal of what fans should inherently want. The team will be better and hopefully for the long haul.
However, if it's the other side of the coin and, bluntly, Breslow continues to be a dud when it comes to the trade deadline, then the Red Sox are going to bottom out. And while it will be frustrating that they didn't sell when they should've and have such a great opportunity to do so wisely, a failure at the trade deadline that results in Boston continuing to be a below-.500 club is going to result in front office changes being made.
At least we've got that going for us. But Red Sox fans should buckle in. There's nothing about Breslow's tenure to this point that suggests this is going to be a comfy ride up to and through the trade deadline if he's going to remain in power with the front office.
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