The Boston Red Sox didn’t just whiff at the deadline—they swung, hesitated, and stared at strike three. Craig Breslow promised action, preached urgency, and then offered caution wrapped in confusion. Now, one $3 million pitcher is at the center of the storm that won’t calm. When your boldest move becomes explaining the one you didn’t make, fans tend to grab the pitchforks.
It’s been 3 days since the trade deadline passed, and the Boston Red Sox are not having it easy from anyone. From the analysts to the fans, everybody has criticized the Red Sox and rightly so, but is it all their mistake, or was there something more to the missed opportunities, like the one with Joe Ryan?
In a recent post, Tyler Milliken, a co-host of the Section10 Podcast, talked about the Joe Ryan deal that didn’t happen. He said, “The Red Sox were ‘close’ to landing Joe Ryan, per @JeffPassan. ‘Boston came close. The Red Sox were willing to part with a number of high-end prospects to land right-hander Joe Ryan from the Minnesota Twins. But that wasn’t expressed until the deadline was nearing, and the Twins were so deep in other talks to disassemble their roster, the prospect of moving Ryan had lost appeal.’“
The Boston Red Sox approached the trade deadline with noise, need, and a roster on the brink. Yet, instead of fireworks, they walked away with flickers—acquiring Dustin May and Steven Matz. Both are arms with question marks: one returning from injury, the other adapting to bullpen life. For a playoff-hunting team, the moves felt more like patchwork than purpose.
The Red Sox were “close” to landing Joe Ryan, per @JeffPassan.
“Boston came close. The Red Sox were willing to part with a number of high-end prospects to land right-hander Joe Ryan from the Minnesota Twins. But that wasn’t expressed until the deadline was nearing, and the… pic.twitter.com/a73tqJdFpQ
— Tyler Milliken (@tylermilliken_) August 4, 2025
Their headline pursuit was Minnesota’s Joe Ryan, the Twins’ ace with a 2.82 ERA and poise. Boston reportedly offered top-100 prospects—Franklin Arias, Payton Tolle, and Jhostynxon Garcia—in various combinations. But the deal collapsed when Breslow refused to part with major leaguers like Jarren Duran or Wilyer Abreu. Despite offering elite talent, the refusal to sacrifice now ultimately doomed the negotiations.
Joe Ryan wouldn’t have been just a deadline splash—he would’ve reshaped Boston’s postseason potential. Pairing him with Garrett Crochet could’ve formed a fearsome duo atop the Red Sox rotation. Instead, they gambled on the present while clinging too tightly to the future. A rotation anchor slipped through, and so might October.
So, was this a front office failure or just a case of deadline déjà vu in Boston? The answer—like the offers—might be a little of both. For all their planning, the Red Sox managed to outmaneuver only themselves. You can’t win the arms race if your best ammo stays locked in the safe. And in the end, Craig Breslow talked about urgency—then traded like he had all the time in the world.
Red Sox fans are still not happy with the deadline strategy used
When the smoke cleared and the phones stopped ringing, the Boston Red Sox had managed to confuse everyone—especially themselves. Craig Breslow spoke like a man ready to make bold moves, then balked when it mattered most. The Joe Ryan saga? Close, but no clarity. Three days later, fans aren’t mourning missed trades—they’re questioning whether the Red Sox ever intended to win the deadline at all.
bresLow is a joke
— Jalen Hurts is the handsomest QB in the league (@handsomehurts01) August 4, 2025
“Breslow is a joke” wasn’t just a comment—it was the mood in Red Sox Nation. Missing Joe Ryan while settling for Dustin May and Steven Matz felt like a comedy of caution. When your blockbuster pitch turns into bullpen patchwork, frustration writes itself in all caps. Boston had the prospects, the urgency, the need—but left the real upgrade in Minnesota
“They’ll land him in the winter, I’m 99% sure of it,” reads like hopeful prophecy. Some fans still believe Craig Breslow is playing chess while everyone screams checkers. If Joe Ryan truly becomes available post-2025, Boston has the assets to make noise. The deadline may have fizzled, but winter gives front offices a second shot at redemption.
“Deep in talks to disassemble their roster, so decided to hold onto the 1 guy who would’ve given them the most return…interesting move lol” sums up the confusion perfectly. The Twins gutted nearly everything, yet held onto their most valuable trade chip. Joe Ryan could’ve brought back a haul bigger than the rest combined. Instead, they trimmed the edges and protected the centerpiece, like flipping the house but keeping the roof. In a sell-off that screamed reset, keeping Ryan whispered mixed signals.
“So they blew it!” isn’t analysis—it’s the gut punch fans felt watching the deadline unfold. The Red Sox circled Joe Ryan for weeks, then ran out of time and nerve. Prospects were dangled, offers were floated, but Boston blinked when it counted most. Instead of a rotation upgrade, they grabbed injured depth and called it strategy. For a team chasing October, it felt like folding with a winning hand.
“No backup plan, and had to panic and offer last minute. lol what a joke” stings hard. The Red Sox reportedly intensified talks for Joe Ryan just before the deadline buzzer sounded. Minnesota, already deep in deals, didn’t have time—or interest—in eleventh-hour drama. With no Plan B, Boston settled for Dustin May and Steven Matz, a far cry from an ace. The chaos wasn’t just missing Ryan—it was never planning for life without him.
Breslow talked like a contender, traded like a placeholder, and left fans clinging to hypotheticals. The Red Sox didn’t just miss on Joe Ryan—they missed the entire point of the deadline. You don’t chase October by asking for a discount five minutes before closing. For a front office that preaches process, this one felt more like improv with no punchline. And now, Boston’s big move might just be explaining why they didn’t make one.
The post Red Sox Fans Turn On Craig Breslow Over Costly Deadline Misstep As Latest Claim on $3M Twins Star Sparks Uproar appeared first on EssentiallySports.