Gunnar Henderson does not have a long-term future with the Baltimore Orioles.
That much we know.
There will be no contract extension at this point for myriad reasons and any reasonable chance to secure more of his service time beyond arbitration was lost within his first six weeks of his ascent to MLB, given how well he performed as a youngster and how his agent, Scott Boras, operates. To say nothing of the frugal way this franchise has been run under multiple ownership groups.
What the industry acknowledges across the board, is that Henderson will be dealt by the trade deadline, same as it was a year ago with Adley Rutschman, the only player Orioles failure baseball exec Mike Elias drafted ahead of Henderson on what’s now an eight-season rebuild. What’s far less clear is when is the best time to deal Henderson given just how pedestrian his 2025 season was, all things considered, and just how much worse he was at the plate, in the field and on the base paths in 2026.
Some caution against “selling low” on a player viewed as an MVP candidate and 40/40 guy just a few years ago. Others point out that there are only a few truly-motivated “buyers” at the deadline each year but with Henderson cheap and young with two years of full control, his market after the World Series would be very robust.
I’ve long been in the camp that auctioning him off at The Winter Meetings should be the goal, and then the other offseason priorities can be set based off the return. Elias is at his miserable worse trying to develop fallen assets on the fly and make cogent in-season moves. And one of the smartest baseball people I know, Fangraphs data scientist and lifelong Orioles fan, Dan Szymborski, tends to agree with me that moving Henderson ASAP makes the most sense.
“I think teams are still going to look at Gunnar Henderson despite his season and there's going to be a lot of belief that he's still a star,” Szymborski, one of the brains behind Fangraphs ZIPS projections, said on “The Daily Flock” this week. “And he can fetch a lot.
“I think there's probably just myriad opportunities to trade Henderson if you're going to go that route, and they probably waited a little long with Rutschman, if you were going to trade him and not extend him.”
A Massive Return
Despite Henderson having a league average offensive season for the most part and seeming visibly frustrated, throwing bats and helmets and letting his hitting issues bleed into the field, MLB execs know what a joke Orioles player development is. And what a joke their coaching staffs are.
There is a speed/power/contact demon still in there (but one this group can't reach or unlock), and many, many GMs will believe they can release it, whether they view him as a shortstop of third baseman. Szymborski, who makes his living quantifying overall player value in the present and projecting for the future, was adamant the Orioles could get a significantly better package of players and prospects than the haul Elias was lauded for getting in return for Rutschman.
“I think you could get more for him,” he said. “Henderson's upside is higher … A Henderson package would be just really, really solid. And I think if you can't extend him, you have to talk about it.”
With not just teams in immediate-go-for-it mode, and early in the offseason when all clubs still have ample time to address needs, there is every reason to believe the Orioles could get MLB-ready help as well as prospects; the Rutschman deal was essentially all for teenagers who are years away from really making a dent in Baltimore.
One For One Swap?
Szymborski agrees with me that fixing centerfield from outside the organization is a sweeping, primary item that must be addressed this offseason and, quite likely, early this offseason. I firmly believe trading two years of Henderson’s career for two years of Byron Buxton’s make sense – baseball and financial as explained in depth here – and the analyst did not disagree. Especially from the Orioles side of things.
“I don't think you're crazy,” he said. “I just don't know if the Twins will do it. The Twins are a very conservative organization, and they love having Buxton, and they love that he wants to be there.”
Szymborski is advocating for free-agent centerfielder Daulton Varsho as a viable stopgap everyday centerfielder, and we go through every key Orioles need and potential trade and free-agent fit as a primer for what will hopefully not be a dud of a offseason in the episode.
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