Orioles’ big offseason plan could crumble if Red Sox strike first

The Baltimore Orioles must upgrade their pitching staff this offseason. More specifically, the O's need to find a top-of-the-rotation starter to pair alongside Trevor Rogers. There are sure to be a number of free agents who'll pique the Orioles' interest, but Mike Elias may want to inquire with the Minnesota Twins to see if Joe Ryan is available.

Ryan could easily become the prize of the offseason. Last winter, the Chicago Cubs were arguably the biggest winners after trading for All-Star outfielder Kyle Tucker. The Houston Astros were able to recoup a nice package in return, but Chicago secured one of the biggest bats available last winter. If the Twins intend to trade Ryan this winter, he could be this year's version of Tucker.

Ryan put together a phenomenal season for the Twins in 2025, going 13-10 with a 3.42 ERA and 194 punch outs over 171 innings of work. Minnesota is smack-dab in the middle of a full-on rebuild, and an arm like Ryan will be quite attractive to a number of contenders; one of whom resides in the same division as the Orioles.

One of the Orioles’ top trade targets, Joe Ryan, could be on the Red Sox's radar, too

The Boston Red Sox, who pulled off a blockbuster of their own last winter when they traded for Garrett Crochet, are likely to be in the market once again for a starting pitcher this offseason. Boston was linked to Ryan at last year's trade deadline, and it's a good bet that they're still keeping a close watch on the Twins' ace.

That could mean a bidding war is about to ensue this offseason between the Orioles and Red Sox, though more suitors could emerge as well. Unlike Tarik Skubal and Freddy Peralta, both of whom are assumed to be on the trade block this offseason, Ryan has more than one year of team control remaining. Ryan's first trip through the arbitration process was just last year, meaning he won't reach free agency until after the 2027 season.

The Orioles will have to make some decisions in the coming weeks, with the biggest one being how to address their rotation. Are they going to add around the edges and find a suitable backend starter or two to add to their coffers, or will Elias and Co. go all in after one of the best hurlers available this winter? If they really want to make a splash, landing a pitcher like Ryan would certainly do it. But they won't be alone in their efforts.