The Red Sox were reportedly close to acquiring Joe Ryan from the Minnesota Twins but ultimately fell short in their pursuit during the MLB trade deadline. Early excitement turned to disappointment after premature reports by MLB Network incorrectly announced the deal, while reliable sources confirmed the negotiations never reached a significant stage.
MassLive’s Chris Cotillo cited insiders from the Twins’ camp who indicated that the Red Sox were far from closing the deal. Meanwhile, veteran baseball analyst Ken Rosenthal criticized Boston’s approach, calling it “feeble at best” and labeling the organization’s deadline efforts as an “epic fail.”
Why Trade Talks with the Twins Unraveled
A detailed investigation by Jen McCaffrey of The Athletic revealed the primary reasons behind the breakdown of talks between the Red Sox and Twins. Multiple sources connected to Minnesota disclosed that discussions fell apart because Boston was unwilling to include any of their major league outfielders or present an attractive enough package of top prospects to Minnesota.
Outfielder Jhostynxon Garcia was considered as part of the potential deal, but the overall offers from Boston failed to meet Minnesota’s expectations. The Red Sox’s proposals lacked the substantial value required to persuade the Twins to part ways with their ace pitcher.
Craig Breslow’s Unsuccessful Efforts to Bolster the Roster
Red Sox executive Craig Breslow acknowledged the challenges following the deadline, expressing mixed feelings about the moves the team was able to make. In a post-deadline video conference, Breslow said,
“We’re happy with the guys we brought in, with Steven [Matz] and Dustin [May], but we also pursued real impact players that we felt like could improve our team in ’25 and beyond.”
He added,
“We were uncomfortably aggressive in trying to pursue them in the players we were trying to put into deals. Ultimately, it wasn’t from a lack of effort. Other teams needed to say, ‘Hey, that’s enough. That crosses the line.’ It wasn’t about an unwillingness to talk about our full system.”
—Craig Breslow, Red Sox Executive
Despite these statements, critics argue Breslow’s pursuit of Ryan lacked the necessary boldness needed to push the Red Sox into contention. For Boston to make a genuine postseason push, the front office must accept some long-term risk in exchange for immediate impact, a balance the team failed to strike during this deadline window.
What Boston’s Deadline Failure Means Moving Forward
The failed attempt to secure Joe Ryan highlights the wider issues facing the Red Sox as they strive to become serious World Series contenders. The city of Boston and its fans expect aggressive moves that send a clear message about the team’s commitment to winning now. Breslow’s conservative approach at the deadline suggests the organization still hesitates to fully commit its assets to a bold path forward.
While the Red Sox did add pitchers like Steven Matz and Dustin May, missing out on a high-impact starter like Joe Ryan could leave the team short in key areas for the upcoming postseason. The expectation now is that Boston will continue evaluating options and prepare for future trade opportunities, with pressure mounting on the front office to be more decisive and daring in the next critical moments.