Aug 31, 2025; Minneapolis, Minnesota, USA; Minnesota Twins starting pitcher Joe Ryan (41) throws to the San Diego Padres in the first inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images Bruce Kluckhohn-Imagn Images

Red Sox May Pursue Twins' Joe Ryan After Trade Deadline Whiff: Insider

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Oct 7, 2025 7:35 AM ET

The Boston Red Sox's offseason needs look a lot like their needs from the trade deadline in July.

Boston is blessed to have a true ace these days in lefty Garrett Crochet. He carried them to their lone playoff win this season, but with myriad injuries throughout the season, the rest of the rotation was reduced to Brayan Bello and a gaggle of young lefties by the end of the campaign.

Back in July, the Red Sox tried to reinforce the rotation by acquiring Minnesota Twins All-Star starter Joe Ryan -- and their failure proved costly as they barely accomplished anything else. Could they try to right their wrongs during the winter?

Red Sox could redouble efforts to acquire Joe Ryan

On Monday, Chris Cotillo of MassLive wrote that another pursuit of Ryan seemed likely, which would make sense not only given Boston's interest in July, but the total teardown the Twins seem to be undertaking.

"It wouldn’t be surprising if the Red Sox made another run at Minnesota’s Joe Ryan," Cotillo wrote. "The Red Sox engaged with the Twins at the trade deadline last July, but couldn’t reach a last-minute agreement."

Chief baseball officer Craig Breslow's sentiments during the season-ending press conference on Monday also at least signaled that a Ryan trade was within the scope of what the front office will be trying to accomplish.

"We need to figure out ways to improve the team and that could take a number of shapes," Breslow said, via NESN. "Every team gets better if you can bring in a starter or develop a starting pitcher that could pitch at Garrett Crochet’s level, right?

“There’s no running from that and we’ll be as aggressive as we can in chasing that down while also ensuring that we’re doing everything we can to develop our players internally.”

Ryan, 29, stumbled a bit down the stretch, but he still finished the season with a 3.42 ERA, 194 strikeouts in 171 innings, and 4.5 bWAR. He has two years left under contract, and although he's a bit older than Crochet was last winter, he'd be an ideal extension candidate to lock up for the rest of his prime.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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