The clock on Gunnar Henderson in Baltimore is already running down.
There’s no realistic path to a long-term extension now, and the reasons are stacking up fast: Henderson got too good too early, Scott Boras does what Scott Boras does, and this front office has never exactly behaved like one eager to buy up extra years. So while the Orioles still have a young star under control, the industry expectation is that he’s headed for a trade by the deadline - just as Adley Rutschman was last year.
The real question isn’t whether Henderson goes. It’s when the Orioles should cash him in.
That’s where the debate gets interesting. Henderson’s 2025 season was only ordinary by star standards, and 2026 was worse in just about every area that matters: at the plate, in the field and on the bases.
That kind of slide naturally triggers the warning against selling low on a player who was once talked about as an MVP type and a 40/40 threat. But there’s another side to it too: deadline buyers are scarce, while Henderson is still young, inexpensive and under control for two more years.
That profile tends to play especially well once the World Series passes and more teams can plan an offseason trade.
Dan Szymborski thinks the Orioles should move faster rather than later. The Fangraphs data scientist and lifelong Orioles fan pointed to Henderson’s still-durable reputation around the league and the chance for Baltimore to pull back a strong return if it chooses to deal him.
“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.”
That belief in the market is rooted in what Henderson still looks like to rival clubs: a player with speed, power and contact ability who hasn’t been unlocked properly in Baltimore. He may have looked frustrated, even visibly so, with the bat tosses, helmet throws and the spillover into his defense, but that doesn’t erase the talent teams think is sitting there.
And unlike the Rutschman return, which was built mostly on teenagers far from the majors, Henderson could bring back immediate help. That matters for an Orioles team that needs answers now, not just someday.
Szymborski also agreed that center field is one of the biggest offseason jobs facing Baltimore, and one that may need to be addressed right away. He didn’t dismiss the idea of swapping two years of Henderson for two years of Byron Buxton, and he was especially clear that the Orioles side of that equation makes sense.
“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.”
If Buxton isn’t realistic, Szymborski sees free-agent center fielder Daulton Varsho as a possible everyday stopgap. He and the host also dug through the rest of Baltimore’s major needs and possible trade and free-agent fits as a setup for what they hope will be a meaningful offseason rather than another flat one.
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