The General Manager Meetings in Las Vegas have opened the door to plenty of offseason chatter, and one idea that fits cleanly on paper is an Orioles-Pirates deal built around each club’s surplus. Baltimore has the infield depth.
Pittsburgh has the pitching. That kind of strength-for-strength match is exactly the sort of thing that can surface when executives start talking shop.
The Orioles have already said their core pieces are “very unlikely” to be moved this offseason, but that still leaves room for a deal if the right partner and the right return line up. And if Baltimore does decide to make a move, the Pirates make sense as a possible fit.
Both teams are trying to get from promising to October-ready, just with different roster shapes. Baltimore has young infield talent to spare.
Pittsburgh has a stronger young starting staff, but not nearly the same kind of infield inventory.
Of course, the biggest names are probably off the table on both sides. The Orioles are not expected to move Pete Alonso or Gunnar Henderson. Pittsburgh, for its part, is just as unlikely to part with Paul Skenes, Bubba Chandler, 2026 All-Star Braxton Ashcraft, Jared Jones, or top prospect Seth Hernandez.
That still leaves some interesting pieces in play beneath the headline names. Mitch Keller, after a down year and now in his 30s, looks increasingly like an afterthought in Pittsburgh. And beyond Hernandez, the Pirates have other arms who could appeal to Baltimore, including Thomas Harrington, Hunter Barco, and Khristian Curtis as possible middle-to-lower-end rotation help.
The tougher question is what Baltimore would actually send back. If Alonso and Henderson stay put, the Orioles’ second- and third-base options become the most logical place to look.
For a lower-budget club like Pittsburgh, players with less track record but real upside could be attractive. Christian Encarnacion-Strand fits that mold after bouncing back in a new setting with a 133 wRC+ in 58 games in 2026.
Coby Mayo is another name that makes sense, especially with his path in Baltimore still blocked. He just posted a career-best season with 24 homers, a 112 wRC+, and 2.0 fWAR.
If the Orioles wanted to chase a bigger pitching return, though, the conversation could move into a different tier. A Jared Jones-type arm would likely require a heavier package, and that’s where Jackson Holliday and Jordan Westburg come into the picture as possible change-of-scenery candidates.
Holliday, the former first overall pick who tore through the minors, has not yet translated that pedigree into consistent big league production. He’s struggled to drive the ball and has run into higher strikeout rates.
Westburg brings a different profile, with a more established major league track record. He was an All-Star in 2024, then followed with a solid 2025 season and a 115 wRC+, but he did not appear in 2026 while recovering from a right UCL injury.
Baltimore also has some cover behind those names. Mayo and Encarnacion-Strand remain in the mix, and Wehiwa Aloy is waiting in the upper minors as a top-10 prospect who can handle third base.
That gives the Orioles room to explore. For now, it’s just a matter of seeing whether the offseason actually pushes this kind of swap from theory into reality.
In Other News...
Orioles Have An Outfield Fix That Makes Too Much Sense
The Orioles spent much of the 2026 season searching for more certainty in the outfield, and the results showed up in the standings and the numbers. Baltimore finished 22nd in MLB with a combined 3.9 fWAR from the position, a reminder that the group never quite gave the lineup the steady production or defensive reliability the club needed. Team president Mike Elias has talked about internal fixes, but he has also left the door open to outside help if the right fit presents itself.
That search naturally points to the trade market, where the Orioles could look for a player who raises the floor on both sides of the ball without forcing a bigger roster shuffle than necessary. Cleveland outfielder Steven Kwan stands out as the kind of target that makes immediate sense for Baltimore, thanks to the way he has contributed offensively and defensively in 2026. The challenge, as always, is whether a player with that profile is actually available and what kind of price the Orioles would have to pay to get him. [Read more 🡒]
Orioles Still Have One Big Bullpen Decision Hanging Over 2027
The Orioles may have spent the winter building out their bullpen, but one of the biggest late-inning questions still sits out in front of them: who gets the ninth inning in 2027? Flix Bautista and Ryan Helsley both have the kind of track records that make them obvious candidates when healthy, and both are expected to be in the mix once they get through their recoveries.
Mike Elias has made it clear the club is not locking anything in yet, and that the answer will depend on how the roster takes shape and how each pitcher comes back. For Baltimore, it is a reminder that bullpen depth is only part of the equation. The real issue is whether either arm is ready to reclaim the high-leverage role the Orioles had in mind when they put this group together. [Read more 🡒]
Orioles Have A Bullpen Need Fans Should Be Watching Closely
The Orioles got by with a surprisingly steady bullpen last season even without key arms like Felix Bautista and Ryan Helsley, but the winter still figures to bring some meaningful change to the relief mix. Mike Elias has already made the clubs direction clear by saying Baltimore intends to add at least one left-handed reliever, a move that fits both the rosters needs and the way the bullpen has been built around depth and flexibility.
That search makes the market worth watching closely, especially with free-agent names like Alex Vesia and Jose Alvarado in the conversation. Both would give Baltimore a different look from the left side, and both come with recent track records that make them appealing fits if the Orioles decide to spend for a late-inning option rather than simply patching the group together. [Read more 🡒]