The Boston Red Sox are heading into the 2026 offseason with a clear mission: bolster their roster to compete at the highest level. High on their priority list is re-signing star third baseman Alex Bregman and adding a power bat to the lineup. But lurking just below these headline-grabbing goals is a critical need that could define their season—a true No. 2 starting pitcher to complement ace Garrett Crochet in the rotation. While the Red Sox have made strides in building rotation depth, the absence of a reliable second starter is a glaring hole. Enter Joe Ryan, the Minnesota Twins’ All-Star pitcher, who could be the answer—but at a cost that might break the hearts of Red Sox Nation.
Joe Ryan is exactly the kind of pitcher Boston needs. At 29, the right-hander is coming off a stellar 2025 season, earning All-Star honors with a 13-10 record and a 3.65 ERA over 171.0 innings. His 194 strikeouts ranked sixth in the American League, showcasing his ability to dominate hitters. With one more year of team control at a projected $6 million, according to Spotrac, Ryan represents both immediate impact and cost-effective value. Pairing him with Crochet would give the Red Sox a formidable one-two punch at the top of their rotation, elevating their postseason aspirations.
The Red Sox know this, and so do the Twins. Trade talks for Ryan were swirling at the 2025 trade deadline, and speculation is rife that discussions will heat up again this winter. But Minnesota isn’t letting their star pitcher go without a fight, and their demands could force Boston into an agonizing decision.
According to Sean McAdam on The Fenway Rundown podcast, alongside MassLive’s Chris Cotillo, the Twins are playing hardball. To land Ryan, the Red Sox would likely need to part with one of their prized young outfielders—Jarren Duran, Wilyer Abreu, or Ceddanne Rafaela—and one of their promising young pitchers, such as Hunter Dobbins, Connelly Early, or Payton Tolle. This is no small ask.
Duran, Abreu, and Rafaela have become cornerstones of Boston’s outfield, each bringing a unique blend of speed, power, and defensive prowess. Duran’s electrifying energy and breakout 2025 season made him a fan favorite. Abreu’s raw power and Rafaela’s defensive wizardry have cemented their places in the lineup. Meanwhile, the Red Sox’s farm system has produced a wave of exciting pitching prospects, with Dobbins, Early, and Tolle all showing flashes of brilliance in their 2025 debuts. Trading one of these young arms, particularly someone like Early, who could be sold high after a strong showing, would sting.
McAdam noted that top prospects like Roman Anthony, Marcelo Mayer, and Kristian Campbell are likely off the table, but the Twins’ demands still hit Boston where it hurts most: their major-league-ready talent. “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 Dobbins or an Early or a Tolle—I think you probably can get something done,” McAdam said. The question is whether the Red Sox are willing to pay that price.
Boston’s rotation has come a long way, but it’s not yet complete. Brayan Bello had a breakout year in 2025, establishing himself as a solid mid-rotation starter, but he’s not quite a No. 2. Lucas Giolito showed flashes of brilliance but was plagued by injuries late in the season, and his potential free agency adds uncertainty. The Red Sox have depth with veterans like Dobbins, Richard Fitts, and Kyle Harrison, as well as prospects like Tolle and Early, but none project as a clear No. 2 behind Crochet. Without a high-end starter, Boston risks entering 2026 with a rotation that’s good but not great.
Joe Ryan could change that. His proven track record and strikeout ability would give the Red Sox a pitcher capable of eating innings and matching up against the best lineups in the American League. But the cost of acquiring him could spark a backlash.
As Cotillo pointed out on The Fenway Rundown, any blockbuster trade for Ryan is likely to upset Red Sox fans. The players in question—Duran, Abreu, Rafaela, Early, Tolle—are not just prospects; they’re young stars who have already made their mark in Boston. Trading one of them would mean parting with a player who has already captured the imagination of the fanbase. “They’re going to do something that ticks off fans—not in a bad way—but by trading away a player you know,” Cotillo said. “It’s going to be somebody who excited you.”
The Red Sox front office faces a delicate balancing act. Trading away fan favorites for a pitcher like Ryan could be seen as a bold step toward contention, but it risks alienating a fanbase that has grown attached to this young core. With Bregman’s re-signing and the pursuit of a power bat already on the horizon, the stakes are high.
The Red Sox are at a crossroads. Landing Joe Ryan could solidify their rotation and signal their intent to compete in 2026. But the Twins’ steep demands—potentially a star outfielder and a promising young pitcher—could force Boston to sacrifice a piece of their future for immediate success. Will they pull the trigger and risk the wrath of their fans, or will they look elsewhere to fill the No. 2 starter void? One thing is certain: the outcome of this trade saga could make or break Boston’s offseason.