There’s a fine line between strategic patience and sitting on your hands, and the Boston Red Sox seem determined to test those limits. Craig Breslow, ever the optimist in a storm, insists his “uncomfortably aggressive” moves were enough. Yet the standings, and perhaps common sense, might argue otherwise. In a league where hesitation is punished, Boston’s deadline gamble could prove painfully expensive.

The Boston Red Sox are winning now, but is it already too late for them to get to the postseason? And if yes, Craig Breslow might be the first person in line to get blamed, and rightfully so. This season started as a mess and is still a mess for the Red Sox, but a little cleaner. And after the Rafael Devers trade, Craig Breslow was already the villain, and the Red Sox not making the playoffs would make that case stronger.

As things stand, the Red Sox have a 74.3 percent chance of making the postseason, and that is a big problem. In the recent article on The Athletic, they talked about the rest of the schedule for August and why this will be a very important month. They wrote, “Let’s not overthink this. These next three games against the Astros are important… the Red Sox are about to go into Yankee Stadium for four games against the Yankees… That would be a huge series even without all the rivalry drama.”

Let us tell this as it is: one slipup and the Red Sox are surely out of the postseason race. When looking at the end of the season, there are 2 glaring mistakes: the Rafael Devers trade and the trade deadline. Rafael Devers and the Red Sox suffered from persistent miscommunication, ultimately triggering a shocking trade. The front office believed he wouldn’t adjust positions, fracturing trust and damaging clubhouse cohesion. That disconnect led to his June departure to the Giants amid fan outrage and mounting frustration. Devers was traded in exchange for two pitchers and two prospects, while San Francisco assumed his full contract.

Craig Breslow’s inaction at the trade deadline compounded Boston’s woes, leaving glaring needs unaddressed. He claimed they were “uncomfortably aggressive,” yet only acquired Steven Matz and Dustin May to shore up pitching. Meanwhile, rival teams loaded up, exposing the Red Sox’s stagnant roster and timidity in high-stakes moments. Growing criticism noted how their deadlock-prone approach may invite other teams to consistently outpace Boston.

Meanwhile, Devers has flourished with the Giants, injecting life into their postseason chase in real time. He’s delivered power and average, sporting around .256 with 22 homers and 80 RBIs in 2025. His clutch homers and leadership have become catalysts boosting San Francisco’s chase for playoff relevance. Devers’s strong output highlights what the Red Sox lost through miscommunication and missed opportunity.

In the end, the Boston Red Sox didn’t just lose Rafael Devers — they lost the plot. Craig Breslow’s brand of “uncomfortably aggressive” feels more like “politely passive” when measured against the AL’s arms race. And while Devers is busy launching the Giants toward October, Boston is busy calculating playoff odds like a desperate gambler. If this season collapses, the ledger will read simple: Devers thrived, Breslow blinked, and the Red Sox paid the price.

3 moves could make the Red Sox fans forgive Craig Breslow, even without the postseason

Red Sox fans have long memories, but they also have a weakness for redemption arcs. Craig Breslow, the man currently wearing Boston’s collective frustration like a name tag, still has a chance to rewrite his chapter. The Rafael Devers debacle won’t vanish overnight, yet decisive, gutsy moves could shift the mood. In Boston, winning isn’t everything—it’s the only thing, especially when the trust deficit is this steep.

Craig Breslow’s tenure as Boston’s chief baseball officer has been a rollercoaster of trust. Every few months, he seems to either win back Red Sox Nation or send them into revolt. The latest heat on him stems from missed trade deadline promises and controversial roster decisions. With the team hot right now, Breslow has a narrow window to solidify long-term support.

One move that could quickly cool criticism is securing Alex Bregman beyond his current deal. Bregman has been Boston’s most consistent bat, a defensive anchor, and a mentor for younger players. Locking him up long-term would signal stability and commitment to building around proven leaders. Such a move could ease the pressure and give Breslow breathing room heading into next season.

Still, words must turn into decisive action, especially after the failed “all-in” trade deadline push. Investing the $27 million saved from the Rafael Devers trade is critical to restoring credibility. Fans won’t forgive careless spending or half-measures disguised as progress in this pivotal offseason. Making targeted, high-impact acquisitions could transform Breslow from a divisive figure into Boston’s long-term architect.

If Craig Breslow wants to finally silence the skeptics, it’s time to stop playing musical chairs with trust. Boston fans aren’t known for second chances — they want results, and they want them now. Extending Bregman, spending Devers’ salary wisely, and fixing past deadline flops won’t just buy goodwill; they’ll prove Breslow belongs in Fenway’s future. Otherwise, he might find himself starring in yet another Red Sox redemption saga — this time, without an encore.