Orioles Face New Roadblock in Pursuit of Twins Star Joe Ryan

A surprising front office shift in Minnesota has thrown a new wrinkle into the Orioles pursuit of ace Joe Ryan, potentially reshaping the trade landscape ahead of Opening Day.

The Baltimore Orioles have made it clear they’re not content with standing pat this offseason. With Opening Day creeping closer, they’re still in the market for a frontline starting pitcher-someone who can slot in at the top of the rotation and help anchor a team looking to build on last season’s momentum. While free agency remains a viable path, Baltimore’s deep farm system gives them the flexibility to explore the trade market for a higher-upside arm.

Names like Shane Baz have floated around, but the Orioles are aiming higher. The dream scenario for many fans?

Tarik Skubal. But the buzz around the league suggests the Tigers aren’t ready to move on from their ace just yet.

That’s left teams looking elsewhere-and one name that keeps resurfacing is Joe Ryan.

The Minnesota Twins and Boston Red Sox reportedly had discussions about Ryan at the trade deadline last year, but the clock ran out before anything materialized. Since then, there’s been a quiet expectation around the league that Minnesota might revisit the idea of moving Ryan this winter, especially considering the value he holds: a recent All-Star with multiple years of team control.

Up until recently, though, the Twins have been signaling that Ryan isn’t going anywhere. Their messaging has been consistent-they plan to contend in 2026, and Ryan is a key part of that vision. But everything might have just changed in a big way.

In a surprising move, the Twins announced they’ve parted ways with Derek Falvey, their president of baseball operations. That’s a major shake-up, especially given the timing.

We’re less than two weeks from spring training, and Falvey had just wrapped up much of the club’s offseason business, including leading the search for a new manager. It’s not the kind of change you typically see from a team gearing up for a playoff push.

Now, Jeremy Zoll steps in to lead baseball operations, while team owner Tom Pohlad will temporarily oversee the business side. And while the Twins are still saying all the right things about staying competitive, actions like this raise legitimate questions about their direction.

For the Orioles, this could be the opening they’ve been waiting for.

If Minnesota’s internal direction is shifting-even slightly-it might be enough to put Ryan back on the table. Baltimore has the prospect capital to make a compelling offer, and with Ryan’s upside and years of control, he’d be a perfect fit for a team ready to win now and sustain it for years to come.

Of course, the price won’t be cheap. Ryan is coming off an All-Star season and is still in his prime. But if the Orioles are serious about contending deep into October, these are the kinds of bold moves that can elevate a good team into a great one.

There’s also the matter of competition. The Red Sox were already in on Ryan once, and if they sense instability in Minnesota’s front office, they could circle back quickly.

Baltimore can’t afford to wait too long. The opportunity is there, but it won’t last forever.

This is where smart, aggressive front offices make their mark. The Orioles have the pieces. Now it’s about whether they’re willing to push them into the center of the table.