The Red Sox were apparently willing to go big at last year’s trade deadline, and the name at the center of it all was Joe Ryan.
Before the 2025 Major League Baseball deadline, Ryan of the Minnesota Twins kept surfacing in Boston rumors. Sandy Alcántara of the Miami Marlins was in the mix too, but Ryan drew the most attention, to the point that FOX Sports MLB mistakenly posted a graphic on social media that made it look like a deal had already been completed.
Boston never landed Ryan or Alcántara, but it wasn’t for lack of trying. Alex Speier of The Boston Globe reported Friday that the Red Sox offered the Twins a package built around Payton Tolle and No. 1 overall prospect Franklin Arias in an attempt to pry Ryan loose.
“The Sox ended up with a deadline fizzle of Dustin May and Steven Matz while whiffing on a much bigger swing,” Speier wrote about the 2025 season. “They made a push to acquire All-Star starter Joe Ryan from the Twins.
According to multiple sources, the team was willing to send Minnesota its top two prospects: High-A shortstop Franklin Arias and Double-A lefthander Payton Tolle. Tolle was aware that his name was floating in the rumor mill.”
Minnesota said no, and Ryan has continued to pitch well this season. Through 21 starts, he owns a 3.38 ERA across 114 1/3 innings.
That makes the Twins’ decision a curious one. Ryan is a two-time All-Star and under team control until after the 2027 season, so there’s obvious value in keeping him.
Still, if Boston really was willing to part with both Tolle and Arias, that was a massive ask to turn away. The Red Sox ended up keeping both prospects, and a year later the picture looks very different: Tolle is part of an elite Boston rotation, and Arias is now one step away from the big leagues.
Ryan remains a strong arm, but the Twins passed on a package that may have been too rich to ignore.
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