Should Red Sox Take Massive Risk, Acquire Former Cy Young Winner?

What is Boston going to do to shore up its rotation?

Apr 4, 2025; Boston, Massachusetts, USA; A general view of Fenway Park before a game between the St. Louis Cardinals and the Boston Red Sox. Mandatory Credit: Paul Rutherford-Imagn Images | Paul Rutherford-Imagn Images

The Boston Red Sox have grappled with a messy pitching rotation in 2025.

Injuries and underperformance have plagued Boston’s staff since before Opening Day.

As the July 31 Major League Baseball trade deadline looms in the not-so-distant future, Boston’s front office, led by Craig Breslow, will most likely scour the market for an impact arm. 

Should Breslow and Boston take a gamble on Miami Marlins ace Sandy Alcántara?

Alcántara, the 2022 NL Cy Young winner, hasn’t been his dominant self in 2025. His stats paint a rough picture— an 8.10 ERA and 1.64 WHIP over 36.2 innings, numbers that scream struggle. Yet, context matters. He’s still regaining his form after missing all of 2024 due to recovery from Tommy John surgery. 

As Bleacher Report’s Joel Reuter wrote on Thursday, “Despite an 8.10 ERA and 1.64 WHIP in 36.2 innings, Alcántara remains a high-profile potential trade chip who’s still working to shake off the rust of a 2024 season lost to recovery from Tommy John surgery.”

“If he can string together a few quality starts, he could still be one of the prizes of the deadline.”

If Alcántara can rediscover even a fraction of his elite form, he’d be a game-changer for a team like the Red Sox.

For Boston, the risk might be worth it, especially since its postseason aspirations might hinge on adding a proven starter. 

Alcántara, 29, offers ace-level upside and team control through 2027. The worst-case scenario would be that Breslow gives up a haul of prospects for Alcántara, and the ace doesn’t return to form within a reasonable timeframe.

On the other hand, if Sandy did whip into shape during the second half, it would look like a genius move.

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