MLB Rumors: Red Sox Linked To Cy Young Winner In Latest Trade Talks Update

So you’re saying there’s a chance? For the second straight offseason, Boston Red Sox chief baseball officer Craig Breslow could trade for one of the game’s top pitchers.

Last year, Breslow shipped prospects to the Chicago White Sox for left-hander Garrett Crochet, who finished second this year in voting for the American League Cy Young Award.

Aces Wild?

This year, Breslow could build a package for the person who’s won the AL Cy Young Award in each of the last two years: Detroit Tigers left-hander Tarik Skubal.

The Tigers have to decide if they want to move Skubal, who’s eligible for free agency after next season and has not shown any desire to preemptively sign a long-term extension.

If Detroit faces losing Skubal to free agency, it may trade the southpaw to ensure that the club receives something in return.

Potential Trade Partners

“Only a handful of teams have the prospect depth and urgency to pull off such a deal,” ESPN’s Jeff Passan reports.

“The Dodgers clearly fall into that category, though their rotation is so good already that they’re focusing their energy on outfielders and relievers. The Mets would be perfect, particularly seeing as owner Steve Cohen wouldn’t blink at giving out the largest contract ever to a pitcher,” Passan adds.

And that’s where things get interesting.

“The Red Sox pairing Skubal with Garrett Crochet at the top of their rotation would give them two of the three best pitchers in baseball,” Passan continues. “The Orioles fit the bill, though with young big leaguers rather than prospects. The Cubs could scrape together enough, but it would gut their system. The Yankees have the upper-level pitching depth Detroit lacks.

“The Mariners have the players but not the desire, even if Skubal did go to the University of Seattle. And while the Brewers could easily put together perhaps the most suitable package, they’re typically the ones who trade impending free agents, not acquire them at a 150% premium,” Passan concludes.

The 28-year-old Skubal led he league with a 2.21 ERA in 2025. His 7.6 WAR and 0.89 WHIP also topped the AL. Skubal finished to Crochet in strikeouts, recording a career-best 241 whiffs.

He’s the first American League pitcher to repeat as Cy Young winner since former Red Sox ace and Hall of Famer Pedro Martinez went back-to-back in 1999 and 2000.

Not only would trading for Skubal give the Red Sox the best 1-2 pitching combo, it would also allow Breslow to clear logjams at a couple of positions, including the outfield and middle infield.