Why the Red Sox are targeting a Joe Ryan trade (again) to beef up rotation behind Garrett Crochet

Starting pitching stands at the heart of the Red Sox‘s needs this offseason. And, a league source told CBS Sports, Boston plans on re-engaging with the Twins on a possible trade for All-Star Joe Ryan.

With Ryan, the 29-year-old pitcher who the Red Sox tried to acquire at the trade deadline, they would have a certified No. 2 starter. The team relied heavily on Garrett Crochet last year, describing him as the stopper, and while it worked perhaps better than even they could have expected (2.59 ERA in 205 ⅓ innings), it’s hard to rely on that again in 2026.

“Aces stop the losing streaks and they keep the winning streaks going,” said Red Sox manager Alex Cora during the 2025 season. “That’s what he’s doing.”

Put Ryan in the mix and the Sox add another arm who can spark runs and stop skids. A move like that would tell the rest of the league the Red Sox are still serious about winning.

For the first time since 2021, the 2025 roster actually made sense. Young players had real mileage on them and a little scar tissue. The veterans knew how to win. They added Alex Bregman, a guy who had never missed the postseason in his nine-year career. They traded for Crochet, the best lefty in their rotation since Chris Sale and David Price, even if the experience gap was obvious.

And even after moving on from their linchpin in Rafael Devers and losing Roman Anthony’s to a season-ending oblique injury in early September, the group carried them. No, they didn’t win the division, but they did secure a postseason berth as the second wild card. Despite the quick playoff exit, the season was largely viewed as a success.

Good starting pitching separates contenders in October. Great starting pitching wins the World Series. This year’s World Series put the gap on full display, flashing what’s ahead of the Red Sox for years to come. The Blue Jays were the best hitting team in baseball, period. The Dodgers weren’t at their offensive peak, but their stars delivered when it mattered, pushing them to a second straight title and a third in six years.

Inside all of that was the real separator: starting pitching.

“What we’ve seen in the postseason is a disproportionate number of runs come via the home run,” Red Sox chief baseball officer Craig Breslow said at the GM meetings last week. “That’s because pitching is so good that it’s really difficult to stack hit after hit and create a rally to push runs across the board. Additionally, the schedule of the postseason naturally allows a team to leverage its best starters and relievers night after night.”

Last August, the Red Sox front office believed they were close to landing Ryan, a move that the club was confident would change their postseason path. But the rumblings out of Minnesota told a different story. The Twins didn’t think Boston came close to meeting their price. Initially, the Twins asked for Roman Anthony in the Ryan deal, which was a hard no for the Red Sox. Then they pivoted to prospects Franklin Arias and Payton Tolle and the Sox were ready to play ball.

However, when the Twins countered again and asked for Jarren Duran or Wilyer Abreu, the Red Sox halted, not wanting to pull impact players off their big-league roster. In the end, a deal between the two sides fell apart.

Fast forward to now and the Twins are largely viewed as a club with no direction, marred by ownership dysfunction. Even with its August fire sale, Minnesota thought it would contend as early as 2027. Byron Buxton was initially adamant about seeing it through. Now, he’s reportedly willing to waive his no-trade clause if it means he can join a contender.

“I think the Twins themselves do not know [if they will contend],” one source familiar with the inner-workings of the organization told CBS Sports. “I do not think ownership knows what it is doing there in terms of its budget. But they know their attendance and TV numbers were bad last year. I think they are more likely to trade Pablo Lopez because of the money he makes than Ryan. If they were to trade both, then I think Buxton would want out and no one would go to any games.”

Ryan comes with two more years of team control. He only made $3 million last year, a number that fits the Red Sox’ penny-pinching approach over the last five or so seasons, and MLB Trade Rumors estimates his arbitration raise would still only hit $5.8 million for 2026. (López, on the other hand, is due more than $21 million next year.) Ryan’s contract certainly wouldn’t be an obstacle for the Red Sox.

Furthermore, given the dysfunction and the likelihood that the Twins won’t contend before 2027, the return they’re looking for might not hinge on pulling big-league pieces from the Red Sox. The deal will look different.

Lastly, given Ryan’s second-half struggles last season (2.72 ERA in the first half against a 4.67 ERA after the break), a Crochet-Ryan pairing should not be seen as some far-fetched goal.

“As we continue to look for ways to improve the team, someone to pitch alongside Garrett is certainly one way to do that,” Breslow said last week.

The Red Sox desperately need a middle-of-the-order bat, especially if they don’t bring back Bregman. And there’s no indication the club is prepared to stretch above its capabilities to keep him.

Pete Alonso could be an immediate fix at first base with the oft-injured Triston Casas heading into 2026 with even more uncertainty. Maybe there’s a trade to be made. If, somehow, the club is able to re-sign Bregman, then the Red Sox have something brewing.

On the pitching side, Brayan Bello took a step forward, with Breslow saying he looked like a legitimate No. 2 starter. That’s generous; Bello profiles more as a back-end arm at this stage. Tolle and Connelly Early are in the picture now, too, though one of them might have to be part of a deal to land someone like Ryan.

So could the Red Sox contend in 2026? Yes. But Ryan is the first step, not the solution.