Pirates feel like natural Orioles trade partners in a strength-for-strength GM Meetings swap

This week, executives across the league have congregated in Las Vegas for MLB's General Manager Meetings. And with plenty of uncertainty about what the offseason will look like, with the lockout all but a guarantee on December 2, this meeting of the minds had the potential to generate some great trade discussions. While Baltimore Orioles management has recently stated that their core pieces are "very unlikely" to be dealt this offseason, very unlikely isn't a 100% certainty, and the Orioles roster goes beyond just core names like Pete Alonso and Gunnar Henderson.

If the front office does decide to pull the trigger on a trade, though, finding the right trade partner is integral. This is where the Pittsburgh Pirates could come into play. Both the Orioles and Pirates are in a similar boat right now as teams with strong core pieces looking to make that breakthrough into October. For the O's, they boast a surplus of young infield talent, but their rotation could use work. The Pirates, on the other hand, have one of the stronger young starting pitching units but, unlike Baltimore, lack in the infield department.

Now, as much as it's unlikely that the Orioles deal names like Alonso or Henderson, it's equally as unlikely that the Pirates move on from stars like Paul Skenes and rising up-and-comers in star prospect Bubba Chandler and 2026 All-Star Braxton Ashcraft. On top of that, younger arms like Jared Jones and certainly top prospects knocking on the big league door like Seth Hernandez seem unlikely to move.

However, the Pirates' starting pitching depth goes well beyond those names. After a down year and now in his 30s, Mitch Keller seems to be becoming more of an afterthought in Pittsburgh as time goes on. And looking at other prospects beyond Hernandez that could be of interest to the Orioles, names like Thomas Harrington, Hunter Barco, and Khristian Curtis could be interesting names to fill out the middle-to-lower end of the O's staff.

What infielders can the Orioles dangle in front of the Pirates for pitching help?

Now, who the Orioles would send to Pittsburgh in this hypothetical remains the biggest question. As established, the likelihood of trading Alonso or Henderson seems low, leaving their second- and-third-base options as the prime candidates to move on from an infield standpoint.

Traditionally, the Pirates have been a lower-budget organization, which makes current O's infield options with more risk or less of a track record, like Christian Encarnacion-Strand and Coby Mayo. Encarnacion-Strand rebounded admirably in his new change of scenery after floundering in Cincinnati two years prior with a 133 wRC+ in 58 games in 2026. Mayo continues to be blocked and thus more of a bench option in Baltimore. However, he's coming off a career-best year where he belted 24 homers with a 112 wRC+ and 2.0 fWAR.

However, if they want to push for possibly a Jared Jones-type arm that still seems like a part of Pittsburgh's starting pitching core, names like Jackson Holliday and Jordan Westburg could be prime change-of-scenery trade candidates to get it done.

Since being picked first overall and then conquering the minor leagues, Holliday has looked below average at best as he's struggled to hit the ball hard and has fallen victim to higher strikeout rates. Westburg, on the other hand, is chasing prior big league success when he was an All-Star in 2024. While still looking solid in 2025 with a 115 wRC+, Westburg failed to make an appearance in 2026 after recovering from a right UCL injury.

With Mayo and Encarnacion-Strand in the mix, as well as Wehiwa Aloy ranking as a top-10 prospect waiting in the wings in the upper minors and capable of playing third, the cover is there for the Orioles to explore possibly trading names like Holliday and Westburg. Now it's just a matter of waiting to see how the offseason progresses in the coming weeks.

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