Gunnar Henderson's trade value is dipping at worst time for the Orioles

The Baltimore Orioles lost 3-1 to the Boston Red Sox on Sunday afternoon, now four games behind Cleveland for the final AL Wild Card spot. The culprit behind the gut-wrenching defeat: beleaguered shortstop Gunnar Henderson, who committed a two-out error in the second inning — which led, naturally, to a three-run bomb from Red Sox outfielder Eli White.

You could hear the frustration in Henderson's voice after the game.

That error was Henderson's 16th on the season. With only two more years until free agency, and with Baltimore once again fading out of contention, it's hard not to wonder what the future holds for the once-superstar.

Gunnar Henderson has significantly damaged his trade value

With Baltimore, like any small-market club, there's a ticking clock on homegrown stars. Henderson, who is represented by notorious bag-chaser Scott Boras, is never going to sign an extension. The consensus has long been that once Henderson reaches free agency, he will be much too expensive for the Orioles to re-sign.

Therefore, there is going to come a time when Baltimore is forced to reckon with Henderson's finite future with the organization. There is going to come a time when Baltimore is forced to consider trading Henderson.

That time may arrive sooner than expected, however. Henderson's close friend Adley Rutschman was just dealt to Boston midway through the penultimate year of his contract. Next season will be Henderson's penultimate year with the O's, and much like Rutschman, he's not quite living up to the hype he once generated.

Henderson won Rookie of the Year in 2023. He was an All-Star and finished fourth in AL MVP voting in 2024. Just two years later, Henderson has piled up 16 errors and fallen into a deep stupor at the plate, batting .222 with a career-worst .706 OPS and 99 wRC+.

He is still a winning player (3.2 fWAR), but Henderson's sloppy execution and crumbling confidence are becoming impossible to write off. It's far too early in his career to completely abandon hope, but the Orioles are working against the clock. If does not age well as a shortstop, that will tank his value. If he can't recapture past glory at the plate, his value crumbles. And the longer Baltimore waits, the less opposing teams will be willing to cough up in a trade. The more club control, the more value he still has.

Should the Orioles trade Gunnar Henderson this offseason?

There are multiple valid takes on a question like this. From the fan perspective, trading your mid-20s cornerstone at a low point is unforgivable. It's the behavior of a cheap front office that is not serious about winning. On the other hand, if Baltimore is skeptical of Henderson's career arc and wishes to maximize his trade value — with two full years of control available to the highest bidder — this winter is the time to do it.

Several factors will play into Baltimore's approach, ultimately. What are the vibes behind the curtain? If Henderson is hitting well in the cages, if he's in high spirits and the coaches are confident in his eventual bounce-back, then the O's probably won't cut bait. If Henderson is sulking, obviously the calculus is different.

It also depends on how serious the Orioles are about contending next season. Baltimore just dropped $155 million on Pete Alonso's doorstep last winter. That contract will not age well; the goal was always to peak within the first couple years of Alonso's tenure. If Baltimore is willing to spend money elsewhere in free agency and really beef up the roster, trading Henderson makes less sense. Conversely, if Baltimore wants to commit wholesale to another youth movement, trading Henderson and building around the likes of Samuel Basallo is the correct path forward.

Which teams can match Baltimore's asking price for Gunnar Henderson?

That would obviously depend on what Baltimore asks for! We can't know the Orioles' price point right now. It's all guesswork. On one hand, Henderson's defensive foibles and two-year downward sprial at the plate raise alarm bells, which dampen his value. On the other hand, he's 25 years old with an All-Star on his résumé. He plays the most valuable infield position and he has flashed all five tools at an extremely high level in the past. There's reason to believe he could get back to such heights in the future, perhaps spurred on by a helpful change of scenery.

The Orioles certainly aren't going to trade Henderson for scraps. It would require a massive haul of top prospects. The best recent comparison point, ironically, might be Adley Rutschman, who reached a similar inflection point with the O's. Baltimore received a package headlined by two stud pitching prospects in Anthony Eyanson and Kyson Witherspoon, both ranked top-five in Boston's farm system by MLB Pipeline at the time of the trade.

These teams could reach the necessary threshold.

Los Angeles Dodgers

L.A. still has the deepest farm system in the Majors, even after trading two top-100 prospects for Tarik Skubal. The Dodgers also have a need at shortstop with Mookie Betts in decline and the financial wherewithal to stomach whatever his salary comes to in arbitration over the next two years. A dark thought, but nonetheless realistic. It also gets Henderson out of the American League, in theory.

Boston Red Sox

A long-theorized landing spot, as the Red Sox need a shortstop. Boston's acquisition of Rutschman, Henderson's baseball bestie, probably won't quiet such theories. That said, the O's might not want to suffer the optics of trading two former cornerstones to a division rival, especially since the Red Sox are more prepared to offer both long-term contracts in free agency down the road.

Seattle Mariners

Another logical AL landing spot that does not hit so close to home. Seattle has a deep farm system and a surplus of quality pitchers, which the Orioles can potentially take advantage of. Baltimore needs to beef of its rotation and the Mariners need more thump in the heart of their lineup. This honestly might be the most sensible landing spot of all, if the O's decide to bite the bullet.

New York Mets

If Henderson's future lies at third base instead of shortstop, the Mets can feel good about pairing Henderson and Francisco Lindor on the left side of the infield (Bo Bichette can move to second base or DH in the meantime). New York is also the richest team in MLB, which would help improve their odds of re-signing Henderson down the road and potentially increase their appetite for trading multiple high-level prospects.

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