BALTIMORE -- The Orioles’ offseason chatter has already started to drift into the kind of territory that gets fans talking fast: big names, big possibilities, and a roster that suddenly looks like it could be reshaped in a hurry.
That doesn’t mean Baltimore is actively trying to move everyone people are discussing. There’s a real difference between listening and shopping, and the Orioles can do plenty of the former without committing to the latter. But with president of baseball operations Mike Elias and new general manager Jared Banner in place, it would make sense for the club to at least hear people out.
And once that door is open, the speculation gets loud.
Could Gunnar Henderson be involved? Could Jackson Holliday?
Could the Orioles use a deal to sort out their infield logjam? Could they flip prospects for major league help instead?
At this stage, almost everything is on the table - almost. Pete Alonso, who signed a five-year, $155 million deal last December, is not one of the names to chase.
Henderson feels like the least likely of the group to go anywhere. The 25-year-old shortstop remains a core piece in Baltimore, even if he still hasn’t fully hit the level the Orioles expect from him since 2024. It would take a massive return to even get the conversation moving.
Holliday is the more interesting name.
He came up in trade rumors before the Aug. 3 Trade Deadline, and teams reportedly checked in on the 22-year-old infielder.
Three seasons and 307 games into his big league career, he still hasn’t reached his full ceiling, but that’s exactly why he draws attention. The talent is obvious.
The pedigree is obvious. He was the No. 1 overall pick in the 2022 MLB Draft and the former No. 1 overall prospect in baseball for a reason.
That kind of profile can bring back a serious haul.
Baltimore’s infield picture is part of what makes the discussion so complicated. The Orioles could end up with five players competing for two spots at second and third: Holliday, Jordan Westburg, Coby Mayo, Blaze Alexander and Christian Encarnacion-Strand.
Westburg missed all of the 2026 season after Tommy John surgery on his right elbow in May. Encarnacion-Strand impressed, though he did it in only 58 games. Alexander can also handle the outfield, but his best defense is in the infield.
If everyone is healthy, Baltimore could piece together a second-base and third-base combination of Alexander and Westburg up the middle, with Mayo and Encarnacion-Strand at third. The issue there is obvious: all four are right-handed hitters, so the mix isn’t exactly ideal. Still, the Orioles would have a workable infield core even if Holliday were moved.
That’s where the trade conversation gets tricky. Holliday is the kind of player other teams believe will keep getting better, and the Orioles are clearly in that camp too.
Moving him would not be a small decision. It would have to come with a return that changes the organization’s outlook.
The Adley Rutschman trade is the reminder here. Nobody saw him getting dealt to Boston on Aug.
- He looked like a long-term Oriole, maybe even until free agency after 2027.
Then Baltimore made the move, and the outside view of who was untouchable changed in a hurry.
Even then, the Orioles didn’t move Rutschman just to make noise. They accepted a massive offer from the Red Sox, one that included four highly ranked prospects and a depth catcher in Carlos Narváez.
If Baltimore makes another move on that scale, it will be because the offer is overwhelming and the front office truly believes it helps the organization.
So will Holliday be traded? Will someone else from that tier be available?
Will the Orioles use their prospect capital to bring in help instead? Right now, it’s hard to say.
What isn’t hard to predict is the noise. The rumors aren’t going away, and they probably won’t anytime soon.
That’s how the offseason works, especially now. Fans want the drama, experts want the speculation, and the Hot Stove keeps burning whether it leads to a deal or not.
In Other News...
Orioles Trade Buzz Now Centers On A Young Core Decision
The Orioles trade chatter has shifted from the usual deadline noise to something far more consequential: what Baltimore wants its young core to look like going forward. Industry speculation has put several recognizable names into the conversation, including Pete Alonso and Gunnar Henderson, both represented by Scott Boras, as teams around the game try to read where the Orioles see their long-term fit. In that same swirl, Jackson Holliday has also surfaced in rumor, a striking twist for a player taken first overall and still viewed as one of the organizations biggest pieces.
What makes the talk around Holliday especially notable is the possibility that Baltimore could be weighing a roster move to make room for Jordan Westburg, which would say a lot about how the club is sorting out its infield and its priorities. None of it amounts to a confirmed trade or an official signal from the team, but it does underline how quickly deadline conversations can move from fringe speculation to questions about the direction of a franchise. For Orioles fans, the intrigue is not just who might be available, but which young players the front office is willing to build around. [Read more 🡒]
Orioles Free Agents Are Heading Into A Brutal Winter Reality
Trevor Rogers is shaping up as the most appealing Orioles free agent on the market, and that alone says plenty about how this winter could unfold for Baltimores departing group. With several teams expected to check in, Rogers sits atop a class that includes a mix of familiar names and uncertain cases, from bullpen help to lineup pieces, all of them trying to sort out what kind of demand they can generate after a season shaped by performance, injuries and contract questions.
Luis Robert Jr., Chris Bassitt, Andrew Kittredge, Zach Eflin, Keegan Akin, Ryan Mountcastle and Heston Kjerstad all bring different appeals and different baggage, which is why the rankings from multiple outlets paint such a wide range of outcomes. For the Orioles, the bigger picture is less about one signing and more about how many of these players can actually find the kind of market they might have expected a year ago, and which ones are left waiting as the winter market settles into a tougher reality. [Read more 🡒]
Orioles Face A Real Catching Question Around Samuel Basallo
The Orioles are headed into an offseason with a familiar checklist, and the catching spot is one of the trickier items on it. Baltimore wants to strengthen its roster in a few places, including the rotation and outfield, but the backstop situation is drawing extra attention because Samuel Basallo is already under a long-term contract and figures to be part of the future.
Basallos bat and upside make him an important piece, yet the club also wants to keep his workload in check to protect his health. That leaves Baltimore weighing a veteran partner who can handle the defensive side of the job, with free-agent possibilities such as Austin Hedges and Carson Kelly in the mix, along with a possible reunion with James McCann. It is the kind of balancing act that could shape how the Orioles manage the position from day to day next season. [Read more 🡒]