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Orioles’ 2025 Winter Meetings preview

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This story was excerpted from Jake Rill’s Orioles Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

BALTIMORE — Few teams have been talked about as much as the Orioles early this offseason.

There was a belief around the industry that Baltimore was poised to have an aggressive winter. The O’s were intent on quickly bouncing back from a disappointing 75-87 showing during the 2025 season and making the postseason for the third time in four years in ‘26.

So far, that’s been proven correct.

Next up: the Winter Meetings.

The baseball world will converge on the Signia by Hilton & Waldorf Astoria in Orlando next week, with team executives arriving Sunday before the meetings take place from Dec. 8-10. More buzz could build around the Orioles, who will continue to lay groundwork for additional offseason moves.

Multiple starting pitchers: Elias has stated multiple times that he wants to acquire a frontline starter to group with right-hander Kyle Bradish and left-hander Trevor Rogers atop the rotation.

“I’ve been pretty clear and direct. We’re trying to find — whether it’s top or front or top half of the rotation, all of those buckets,” Elias recently said. “We’re trying, and there are guys out there, and we are in pursuit of every one of them.”

The Orioles will also aim to bring in some additional depth for their rotation landscape.

Another impact bat: Ward will help solidify the middle of the lineup, but Baltimore could still add another veteran to bolster an offense that underperformed in 2025. If the O’s can land a top slugger, they’ll find a way to make him fit onto their roster.

A third catcher: Adley Rutschman and Samuel Basallo will often be in the same lineup, as one will frequently start at designated hitter when the other is at catcher. Plus, Basallo will also get time at first when Rutschman is behind the plate.

It could be beneficial to carry a third catcher on the 26-man roster so that the Orioles won’t risk losing their DH if an in-game injury occurs.

Potential trade candidates
Elias said Ryan Mountcastle is “a big part of our picture right now” when the 28-year-old was tendered a contract on Nov. 21. But it continues to feel like there are too many first basemen on the Orioles’ roster, with Coby Mayo and Basallo also in the fold.

Mountcastle and Mayo are both right-handed hitters who will play only first base and designated hitter in 2026. It would make sense for Baltimore to move one of the two because of their similar profiles. And with Mountcastle set to become a free agent next offseason and Mayo showing great improvement during the second half of 2025, Mountcastle would be a prime trade chip.

Prospect to know
Enrique Bradfield Jr. (the O’s No. 4 prospect per MLB Pipeline) has a good chance of reaching the big leagues for the first time in 2026. The 23-year-old center fielder finished the ‘25 season at Triple-A Norfolk, then went and played 20 games in the Arizona Fall League.

With 80-grade speed and a 70-grade glove, Bradfield has a skill set much different from anybody currently on the Orioles’ roster. The 2023 first-round Draft pick could soon get an opportunity in center, where Baltimore is set to start Colton Cowser despite the team’s preference to play him in a corner in recent years.

Rule 5 Draft
None of the players on the Orioles’ Top 30 Prospects list are eligible to be taken during the Rule 5 Draft on Dec. 10. The O’s also recently protected right-handers Anthony Nunez and Cameron Foster and outfielder Reed Trimble by adding them to the 40-man roster.

Baltimore selected at least one player in the MLB portion of the Rule 5 Draft every time the event was held from 2006-22, but it didn’t take anybody in ‘23 or ‘24. It feels more likely the Orioles could pick up somebody this year because of their uncertain landscape in the bottom half of their bullpen.

Burning question
Could the O’s reel in one of the marquee free agents on the market?

The Orioles have already shown aggressiveness this offseason, and they’ve expressed a willingness to expand their payroll. But Baltimore has still never made a huge free-agent splash since Elias became the head of the baseball operations department in November 2018.

Perhaps that soon changes.

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