Back in April, few expected the Red Sox to still be standing in the playoff picture come late July. But here they are within striking distance, with momentum building, and a young core finally showing signs of something real. Fenway’s getting louder, the clubhouse feels energized, and yet, the front office remains quiet. Too quiet.
That’s exactly what ESPN’s Buster Olney is concerned about. On NESN’s 310 To Left podcast, the veteran insider didn’t tiptoe around his take; he warned that Boston, under Chief Baseball Officer Craig Breslow, is at serious risk of letting a winnable American League slip right through its fingers. While the rest of the AL stumbles or stalls, Olney sees a clear opening. But he’s not sure the Red Sox will have the guts to take it.
“If you make the right moves, you could be the 2023 Texas Rangers,” Olney said. “There are no great teams in the American League right now… This could be your shot.”
It’s not just speculation. Olney pointed to recent history, Theo Epstein’s gutsy 2004 trade of Nomar Garciaparra and his aggressive 2016 deadline deal for Aroldis Chapman in Chicago. Both were shocking moves at the time. Both led to World Series banners. That’s the playbook Olney believes Boston needs to follow now: lean into risk, trust the vision, and stop managing from fear.
But that’s where it gets complicated. Trading someone like Jarren Duran, the emotional heartbeat of the current roster, could rattle the fanbase and fracture clubhouse chemistry. NESN’s Alex Speier acknowledged the dilemma, calling Duran a role model for younger players and a symbol of the team’s gritty identity.
Still, Olney’s point is hard to argue. The AL isn’t going to stay this open forever. The Yankees might get healthy, the Astros might reload, and Baltimore’s youth movement isn’t slowing down. This is the soft spot in the schedule, and Boston has to swing now, not in theory, but with action.
The question hovering over Breslow’s office is simple: Is he willing to be bold when it matters most? Because if not, this 2025 team could go down as the one that almost was in a year where almost just might’ve been enough.
Breslow’s silence could be costly for the Red Sox.
At a time when the American League is wide open and the Red Sox are flirting with contention, Craig Breslow’s quiet approach feels more unsettling than strategic. The deadline is approaching, the window is cracked open, and yet Boston’s front office seems more content watching than acting. It’s a dangerous game, especially when your competition is circling upgrades like sharks smelling blood. The fear isn’t just missing out on the playoffs. It’s wasting a ready roster, or at least, could be with the right support.
And here’s the real concern: we’ve already seen what happens when Breslow misreads urgency. Take the Rafael Devers situation. A communication breakdown over Alex Bregman reportedly pushed Devers into a corner, ultimately leading to his stunning trade to the Giants. Boston’s return? Promising, but nowhere near what you’d expect for a homegrown franchise slugger under contract for nearly a decade. Or look at the Walker Buehler signing, a $21 million flyer on a broken ace who’s pitched to a 5.72 ERA in 2025. These aren’t just hindsight misses; they’re examples of decisions that lacked foresight and feel.
Breslow’s resume also includes trading away Chris Sale, who went on to win the NL Cy Young for Vaughn Grissom, a player still stuck in Triple-A a year and a half later. And don’t forget Luis Garcia, the reliever acquired at the 2024 deadline who posted an 8.22 ERA in 15 appearances, single-handedly sinking multiple games. These weren’t minor missteps. They were loud, public failures, and they happened because Breslow either acted too late or not decisively enough.
With the 2025 Red Sox showing legitimate life, his silence now could echo even louder by season’s end.
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