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Inside The Orioles

Brace Yourself Birdland, Gunnar Henderson Is The Next Oriole All Star To Go

Orioles top baseball exec Mike Elias is emboldened by the Adley Rutschman trade and more set in his ways than ever, and Henderson's days inn Baltimore are short
May 27, 2026; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) celebrates with Baltimore Orioles catcher Adley Rutschman (35) after hitting a home run during the first inning against the Tampa Bay Rays at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images
May 27, 2026; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) celebrates with Baltimore Orioles catcher Adley Rutschman (35) after hitting a home run during the first inning against the Tampa Bay Rays at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | IMAGN IMAGES via Reuters Connect

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The Orioles, under the nightmarish reign of Mike Elias, are utterly predictable. Their core beliefs are financial, winning is ancillary, and value always reigns supreme.

Billionaire owner David Rubenstein came out of hiding to shame himself by talking up clown baseball exec Mike Elias before the deadline, because he’s truly enjoying the way he operates on the financial margins to ensure the requite return on investment. That’s all this is. Private equity line items.

Elias has been running the same perpetual-rebuild grifter’s playbook – it’s the only way he knows to operate – so the past is always a portal to the present. This is a proven baseball failure who won’t change and is surrounded by inept sycophants who provide no pushback. This guy just showed you again in speaking about these trades that he thinks he can lie and gaslight about what he’s accomplished and what a joke franchise actually is.

All of which is a preamble to tell you that Henderson is absolutely gone in the next calendar year and I deeply, deeply, expect it comes directly after the new CBA is worked out (assuming owners don’t get the “franchise-tag” type mechanism they are plotting for a la the NFL). Just like we knew Rutschman was always gone by this just past trade deadline, we’ve had August 2027 circled for Gunar for years. It makes sense for the exact same fiscals that always made sense for Adley.

And this past trade deadline, with the only people who matter to Elias (the billionaires), serving only to embolden his cowardly and craven acts, they are more stuck in than ever. As for the people who pay the freight with their wallets in Birdland, the customers, they stopped mattering a long time ago.

On The Clock

Trading players with multiple years of arbitration control left just makes sense, and for owners who only care about value, waiting beyond that with players of this magnitude is silly. Elias is also all about ego – he is a steward for himself not this franchise – and he loves reading about how great he allegedly did for Rutschman, gushing about being "overwhelmed" by Boston’s offer. He cares much more about prospect rankings than standings, and he can fetch way more for Henderson – even in an ugly one-year funk – than he could for Adley in a horrible two-year funk.

Even when Elias has a quality team he wants to sell – or pretend to be a buyer at best – because looking smart and landing suspects and turning them into prospects (not actually winning MLB ball players, mind you, just “top 100 prospects”) is his kink. The rush of self-congratulatory adrenaline from the Adley trade has him lusting for more, with one obvious chip to play.

He also wants to stay in the good graces of mega-agent Scott Boras no matter what.

Boras has the best players Elias will never sign in their prime, but he needs to keep finishing second or third in the chase for top free agents (reportedly, hat tip national and local media) to fuel his grift. It creates a fake reality that this fraud is actually working for a living and cements the idea that baseball economics are the boogeyman, but, boy, did Mikey give it his all! A for effort!

He needs Boras, and the media, to launder the quasi-details of almost-signings.

Elias also knows any chance to extend Henderson is long gone, and Boras knows that Orioles player development sucks and is a big part of Henderson’s problem. He ain’t selling low on a kid this talented and there are never hometown discounts to begin with when it comes to Boras. He’s gotta be pissed with them diminishing his jewel.

We told you all along Adley was ready to go a long time ago – for good reason being stuck with mook managers and with losers running the front office – and we strongly believe Gunnar is right there with him. Getting him out of here on the heels of Adley, sooner rather than later, is right up Elias’s alley.

Also, if Gunnar is gone and Elias agrees to give Jackson Holliday (Boras client) a real run at shortstop – can’t you see it already, with Blaze Alexander at second and Jordan Westburg (Boras client) at third? – well, what a great way to keep Boras happy. Try to boost Holliday's worth and potential and smooth the groundwork for Gunnar to say nothing but great things about having to work for Elias and these idiots on the way out.

That’s how the sausage is made, folks.

Henderson has a .698 OPS in his last 163 games with 160 strikeouts to 62 walks. He’s been engulfed in frustration with no one on this staff able to reach him. He's among the most error-prone players in MLB and is providing nothing when on base. With no help in sight.

And if we know Elias is a loser who doesn’t really want to win, trust me that clubhouse knows. Which is why Elias wouldn’t even commit to meeting them on Tuesday to discuss his deadline actions like a man.

Then again, he had to fly to Texas to apologize to the first decent ballclub he ever had in August 2022 (which spawned the infamous “liftoff” press conference). And he wasn’t man enough to meet the media after pretending manager Brandon Hyde was the primary reason the 2025 Orioles stunk so bad.

Yeah, says here Gunnar has seen and heard more than enough. Boras sure as hell has. And Henderson will spend the next few summers somewhere other than Baltimore once we get to 2027.

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Jason La Canfora
JASON LA CANFORA

Jason La Canfora has covered the NFL and MLB for decades and currently covers the Ravens and Orioles for On SI.

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