Since the middle of the 2025 season, the Boston Red Sox trading for Minnesota Twins All-Star pitcher Joe Ryan has been at the forefront of fans' minds.
The Sox couldn't swing a deal to bring him in for their postseason run, so they turned to Dustin May instead. Still, Boston fans hope it can make something happen to net a clear No. 2 starter to bolster its rotation behind Garrett Crochet.
Ryan has two years of team control remaining on his deal with the Twins, and it will take quite a trade package to entice them into an exchange. Luckily, the Red Sox have more than enough big league players and top prospects they can afford to move for such an arm. Red Sox insider Chris Cotillo's proposed trade package
“If you start a Joe Ryan package with one of your major-league outfielders and one of the pitchers that broke through — whether that be a [Hunter] Dobbins or [a Connelly] Early or a [Payton] Tolle, I know those are varying degrees of value — I think you probably can get something done for anybody, especially if you include [Jarren] Duran or [Wilyer] Abreu or [Ceddanne] Rafaela," Cotillo said on the October 6 episode of the "Fenway Rundown" podcast.
Red Sox insider Chris Cotillo's proposed trade package for Joe Ryan is absolutely feasible for Boston
Cotillo said a major league outfielder and one of the top prospect pitchers would start a potential trade package for Ryan, but given the scale of Boston's resources, that's a great start. Even if Minnesota asked for another top prospect, that'd be a very reasonable package for an arm such as Ryan's.
The Red Sox have a well-established logjam in their outfield with Duran, Rafaela, Abreu, Roman Anthony, Masataka Yoshida, Jhostynxon Garcia and even Kristian Campbell vying for starting roles in 2026. The same goes for their rotation — with Crochet at the helm and (hopefully) a free agent or trade acquisition in the No. 2 slot, Boston still needs to find spots for Dobbins, Early, Tolle, Brayan Bello, Kutter Crawford, Patrick Sandoval, Richard Fitts and Kyle Harrison, with a new crop of top pitching prospects in the farm system after Craig Breslow's 2025 draft.
Boston has plenty of resources to swing a deal for Ryan without exhausting too much of its depth, especially since the trade deadline has come and gone. Not only have the stakes lowered since the postseason has passed, but Ryan's second half performance didn't live up to his showing from the first half of the season. Ryan clocked a 2.72 ERA and a 0.91 WHIP over 109.1 innings before the All-Star break and a 4.67 ERA with a 1.25 WHIP in 61.2 innings after, which could lower the Twins' asking price, although only slightly.
Another top-tier starting pitching acquisition should be among Boston's top priorities this offseason so it can remain competitive in the AL East alongside the Blue Jays and Yankees, who each made deeper playoff runs than the Red Sox. Trading for Ryan could be one of the best ways to do that, and the Sox's farm system is deep enough that the prospect losses would be worth it.