The best time to trade Gunnar Henderson is right after the World Series.
I'm not here for the "selling low" yammering because he has been in a two-year slide and there is zero indication that Mike Elias does anything but make such things worse (see: Adley Rutschman) and selling with two full years of control reaps the greatest rewards, as Fangraphs.com data maven and O's fans Dan Szymborski, who quantifies player value for a living and is one of the best at it, explained recently .
Furthermore, Elias is particularly terrible at addressing team needs in-season, at the trade deadline only contending teams would want Henderson, while a good 20 teams might listen on him now. By doing this quickly, Elias can have the entire rest of the offseason to address shortstop, it brings other needs into focus (depending on how much MLB-ready stuff you get for Henderson), and as more analysts are pointing out, with a lockout looming there is an expectation teams will splurge early based on the existing CBA in place , rather than wait until after the lockout with a new economic system (Henderson/'s agent, Scott Boras, is all but guaranteeing it).
History tells us that would be the case, so budgets will be blown and big moves will be made and far better to have Henderson be a part of that rather than try to market him down the road. He isn't going to be here after the trade deadline anyway and the window to do an extension closed years ago.
So, um, what if Elias does what he always does and craps the bed entirely? And tries to run it back with Henderson in hopes he gets back to being a 30/30, MVP candidate who could fetch all the prospects Elias covets in early August? Well, if Henderson is here Opening Day, I am in the business of offering suggestions and solutions to help the Orioles win, now, because prospect lists and future value is a fool's errand with this mook in charge.
Maybe the new "GM" could help push a four-pronged plan like this. And private equity billionaire David Rubenstein couldn't object much because this shouldn't cost much. If they do keep Henderson, this would be by plan to rebuild him:
Jun 7, 2026; Toronto, Ontario, CAN; Baltimore Orioles shortstop Gunnar Henderson (2) misses a tag on Toronto Blue Jays second baseman Ernie Clement (22) for a fielding error in the sixth inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images | IMAGN IMAGES via Reuters Connect
Yeah, this is going to complicate things for Elias and his vanity projects (Christian Encarnacion-Strand) and third is already a cluster. But I am starting the process here.
Henderson's fielding funk - years in the make - impacts his state of mind and bleeds into his at bats. He is a natural third baseman, everyone from Jim Duquette to Buck Showalter to Dan O'Dowd has said that on "The Daily Flock" and they need to get a glove-first field general to fix their horribly broken spine and that's not Henderson.
Not having to worry about double-play exchanges anymore and leaning into the athleticism and instincts. Having to make fewer throws from fewer angles would be a big help (the arm has been a problem since early on with accuracy and consistency) and if you had a Joey Ortiz type at short it would make the third baseman's life much easier.
"There are great players that understand how they're great and why they're great," O'Dowd explained this summer, "and there are great players who have no clue about what actually makes him good. So it could be an aptitude issue on his part, or it could be that they've never taught him what makes him special as a player.
"Defensively, there is absolutely no reason - he fundamentally at times does not actually field the ground ball the right way. That's a lack of fundamental teaching."
Life would be easier at third.
Aug 17, 2026; Minneapolis, Minnesota, USA; Minnesota Twins center fielder Byron Buxton (25) reacts after hitting a single during the fourth inning against the Atlanta Braves at Target Field. Mandatory Credit: Jordan Johnson-Imagn Images | IMAGN IMAGES via Reuters Connect
It's pretty clear that none of Elias's Glory Boys can be THE MAN, or even really want to be THE MAN or know how to go about being THE MAN. Now, The Polar Bear is the THE MAN, but come to find out as I said all along, one veteran bat ain't fixing this. You find, oh, I don't know, a Byron Buxton type to toggle with Alonso between third and fourth in the lineup, or second and third, and I can get with that. At that point you put Henderson anywhere and he should be better.
You get another bat like that and you have Henderson lead off against righties knowing he has Buxton and Alonso behind him, he will get in base and work quality at bats. Because those two will work him over if he's trying to hit solo homer after solo homer. Doubles to the gap become runs in that structure.
Or get a real leadoff guy, bat Henderson second and have those two behind him before you get the Samuel Basallos and Coby Mayos. Either way, the lineup dynamic needs to shift in a meaningful way. Henderson is a short-timer now, no matter how you spin it, and finding another mid-order thumper who also gets on base to be the Robin to Alonso's Batman beyond 2027 is a massive need no matter what and it needs to be filled in a real way.
Elias seemed to know this when he traded for Taylor Ward, but that became just another right-handed bat that fell prey to Sig's Wall in left field . So is we make a similar move and it's another righty bat (like Buxton) he needs to have an All Star profile like Buxton and ideally could play centerfield, like Buxton.
"With the one through five hitters, you know, how bad they've been," former O's exec Jim Duquette told us this summer, "it doesn't take a genius to see that Gunner Henderson's been struggling all year. And it goes back to last year, and you can see the frustration on a regular basis when he has an extended period of struggle.
"I still believe in the talent. He's a really talented player, but the value has gone backwards."
Needs help.
Sep 5, 2026; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) reacts to a strikeout during the third inning against the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | IMAGN IMAGES via Reuters Connect
Henderson is too good to be this bogged down. Some guys thrive on all the numbers and minutia and data and breakdowns. Seems to me that hasn't served this young man all that well. Less is more.
Likewise, bragging about all the hours he spends in the batting cage trying to harness this or do exactly that and adjust to all the "help" a succession of failed data-driven hitting coaches have foisted upon him isn't smart. Henderson's default to everything is to do more and try more and they need to figure out when to back off him, when to just drop him in the lineup and let him figure some things out for himself with less pressure on him, and how to connect with him as a human being.
The industry is baffled how this situation has become this bleak, and it's about more than baseball. There has been a clear disconnect with how they have tried to go about making him better and where that has actually led all involved.
"Hitting-wise, if you look at how he moves as a player in the box," O'Dowd told me, "from when he first came up ... and got over the hump, he's not moving the same way. He's just not putting himself into the same positions to get his swing off as he did when he first came up, which tells me he didn't know what he was doing."
Aug 16, 2026; St. Petersburg, Florida, USA; Baltimore Orioles manager Craig Albernaz (55) looks on during the fifth inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect
If you keep him here as your signature player and your last hope that someone from Elias's first draft class ever wins a playoff game in Baltimore, then you need to alter how you handle him. All the sucking up and over-coddling and deifying Rutschman when any sound baseball person could see the decay start to set in during the 2024 playoff push, didn't serve the player or the team.
This paradigm where Henderson and Jackson Holliday must be talked about in a ridiculous manner like they are infallible, while Craig Albernaz tries to deliver public whippings to Basallo and Recce Hinds and Jeremiah Jackson won't work. It will split a clubhouse and you can't play obvious favorites like that as the great Mike Bordick pointed out to us at length .
He is their most talented player, he has the highest upside, and if you move him to a position where he can best succeed and add a real bat to take pressure off him and stop inundating him with constant tweaks and adjustments, you also need to hold him accountable to a degree they've never come close to doing before no matter who the manager is.
If the puppet skipper is threatening a 2027 tough guy routine, best apply to all, especially considering from a fundamental standpoint (picked off twice in the same game, leading the league in errors at his position, a failure with men on base) Henderson was the biggest offender. I strongly believe the kid can take it and actually it probably makes his skin crawl the way they gaslight and lie and bend over backwards to excuse inexcusable play.
This article was originally published on www.si.com/mlb/orioles/onsi as If The Orioles Don't Trade Gunnar Henderson, Here's How To Fix Him For Birdland .
