With MLB’s annual winter meetings getting underway in Orlando, FL starting Monday, it’s about to be a busy three days of news for all 30 teams across the majors.
One team that hasn’t stopped making noise all offseason is the Boston Red Sox, who are seemingly attached to any and all free agents, and are in the discussion for just about every prominent player being dangled on the trade market.
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Even with MassLive’s Sean McAdam reporting in late November that Red Sox ownership is concerned about exceeding the $244 million Competitive Balance Tax threshold in 2026, their prominence on the hot stove rumor mill has been unmatched.
With that said, a report came down on Monday that has the Red Sox moving away from one of the offseason’s hottest names on the trade market, confirming some tea-leaf reading that was being done by yours truly over the weekend.
According to my friend and colleague Rob Bradford of WEEI, the Red Sox have drawn back on their pursuit of the Twins ace Joe Ryan after making him a primary target in late July earlier this year.
This reporting is the finale of a group of reports/moves that make this outcome an obvious one for Boston. And while we all know to never say never when it comes to free agency in any sport, it appears – for the moment – this dream for Red Sox fans might be dead.
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Here’s how everything connects:
– On Thursday, Pirates righty Johan Oviedo was traded to Boston for a minor league package highlighted by outfielder Jhostynxon Garica. This move came just nine days after trading significant minor league compensation for Cardinals righty Sonny Gray
– One day later, Ken Rosenthal reported that the Twins “aren’t anticipating a trade of Joe Ryan,” which was noteworthy for Boston fans given how publicly the flirtation was back at the trade deadline (we all remember the Instagram posts)
– When you consider the aforementioned McAdam report, along with multiple media reports saying Boston was shifting its focus towards pursuing help on offense rather than pitching shortly after the Gray deal went down, it’s as if the combined reports were saying the quiet thing outloud
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– Boston, given their self-inflicted financial constraints, must have told Minnesota they no longer wanted to pursue a deal for Ryan because they were saving their money to sign a bat (or two) like Kyle Schwarber or Pete Alonso.
– Fast forward to Monday, and Bradford’s report along with multiple media reports saying Alonso is driving from his home in Tampa to meet with Boston in-person on Tuesday paints an extremely clear picture of what type of offseason the Red Sox are planning on having.
Sep 20, 2025; Minneapolis, Minnesota, USA; Minnesota Twins starting pitcher Joe Ryan (41) reacts to Cleveland Guardians catcher Bo Naylor’s (23) solo home run during the second inning of game one of a double header at Target Field. (Matt Krohn/Imagn Images)
Boston reportedly taking themselves out of the Ryan is not surprising given the context, yet is still frustrating for Red Sox fans.
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So, heading into the offseason, Ryan remain atop most fans’ wish lists, especially with trade market prices typically lower in the offseason. With that logic in play, Boston should have been more willing to deal with the Minnesota for the All-Star at a fairer price than what was reportedly discussed at the deadline.
The caveat with Ryan is this:
He’s almost certainly going to want an extension anywhere he’s traded, as he faces two arbitration years in 2026 and 2027. Securing his contract now would give him long-term financial security and lock in his salary before arbitration, directly increasing the acquiring team’s future payroll obligations.
At his age and after the season he had for a struggling Twins team – 3.42 ERA with a 13-10 record across 171.0 innings pitched – Ryan is deserving of some financial security. Securing a long-term contract now could protect him financially from instability if a salary cap is introduced after next season, which players across baseball are anticipating and preparing for by seeking deals early.
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But as we’ve laid out, that’s no-go for Boston given their additions of Oviedo and Gray. They’ve made it abundantly clear that a more affordable route with starting pitching will allow them to avoid as many CBT penalties as possible as the team remains in pursuit of improving their offense.
So if Monday’s reports are true, a clear No. 2 starter behind Cy Young runner-up Garrett Crochet will have to start thinking about pitching somewhere outside of Boston for 2026.
Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He’s a senior digital content producer for WEEI.com, and a native of Lincoln, RI.