The Orioles Player Most Likely To Be Traded This Offseason

You can tell a lot from the way a professional sports team dollops out half-truths and quasi stories. It’s always strategic and worded in specific ways.

There are clues and tells about who it came from and what it really means and what the team’s motives are. In the case of the recent huge scoop about the Orioles being ready to wheel and deal anybody and everybody, two names were chosen to be clustered outside of everyone else. Pete Alonso – who, honestly, I’d be quite open to trading as well given his age and the fact it’s highly likely last year was the best year you’re going to get from him on this deal – and Gunnar Henderson (who absolutely should be the first to go ), both of whom are represented by Scott Boras.

Seems everybody can see that this team has a glut of infielders and there's no way they can run it back, and they bady need starting pitchers (multiple) and outfielders (multiple) and these guys tend to be pretty easy to see through.

Hmm.

Follow The Money And Follow The Agent

Sep 13, 2026; Toronto, Ontario, CAN; Toronto Blue Jays left fielder Charles McAdoo (26) steals second base as Baltimore Orioles second baseman Jackson Holliday (7) misses the throw from catcher Samuel Basallo (not pictured) during the second inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | IMAGN IMAGES via Reuters Connect

One guy who most wouldn’t think the Orioles would have any interest in shopping as the only long-term free-agent contract Elias has ever executed, and the one who the industry knows will never sign an extension with them and will be dealt by the trade deadline like Adley Rutschman was a year ago. We know from years of covering this team, with how deep Elias is with Boras clients, and from the way the Boras gasses him up in the media that these two have been in cahoots in the past. And we find it pretty interesting that Jackson Holliday, a first-overall pick from just a few years ago, wasn’t mentioned among those who aren't being shopped.

Wonder why?

We’ve long suspected Holliday’s father, Matt, a fairly legendary player, could see through Baltimore’s player development failures and is probably frustrated by them (rightfully so). As a former player he has a unique understanding of the pressure and weight that comes with where his son was selected and with how this was going and it was known around the league that Holliday was being marketed ahead of the trade deadline.

And his season fell apart in August and September.

I think this is a wrap, folks. I’m suspecting Boras knows by getting Holliday elsewhere, it opens up a natural slot for Jordan Westburg – yeah that’s his client, too – to go to second base, where he needs to be at this point and might help him finally stay healthy. And if Henderson is still here, he’s obviously at shortstop (or maybe third if anybody wants to do the right thing), and at some point a few of these Boras guys were always going to have to get moved out.

Pretty sure I know which one is headed out. And I don’t think for a moment, by the way, that Henderson is untouchable but Elias wants rivals to know how high he thinks the price should be. And Boras would, too, because he’s got a lot of work to do to rebuild the player’s value and being the centerpiece in a blockbuster couldn’t hurt.

They may need to try to package Colton Cowser with Holliday to make it look like the Orioles got something back in return, but it was no accident that Holliday’s name was suddenly everywhere before the deadline. And I doubt he’s here at spring training.

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