It's Over For Jackson Holliday With The Orioles. Even Mike Elias Has To Know It

The best time for baseball failure Mike Elias to trade one of his failing former top draft picks is, invariably right now.

Because the longer they persist in his laughingstock player development strata – and the more they toil under what’s been a disaster medical and training staff - invariably their future value will decline and things will only get worse. Among Elias’s superpowers, wrecking top prospects is right up there with building third-grade rosters, hiring inane managers and constructing teams incapable of catching the ball or executing baseball fundamentals.

Which brings us to Jackson Holliday, Elias’s second first-overall selection (with his overt tank forcing even the craven and cynical billionaires who run baseball to change their draft rules), and why he needs to go this offseason. And to be clear Holliday needs to go ASAP as badly as Elias’s first overhyped first-overall pick, Adley Rutschman, needed to be jettisoned before the trade deadline. Long a Holliday skeptic myself – I begged and pleaded them to make him a cornerstone inn a Tarik Skubal package back in 2024 - I tried to keep an open mind that sweeping midseason stance and swing corrections might turn him around, but that was folly.

It’s time for him to be packaged (ideally with failed fifth-overall pick Colton Cowser as should have happened at the deadline) this winter.

This won’t get better here, and we have to operate now with the known constraints moving forward” Elias is as empowered as ever, overmatched puppet skipper Craig Albernaz is back for 2027, and the idea these mooks are going to turn Holliday into a winning centerfielder is ridiculous (though several top analysts believe it can be done). They couldn’t turn him into a competent second baseman after perpetual grifter Elias sold you he was a five-tool All Star shortstop when he drafted him.

Again, I watched him throughout the minors, called this out as an overhyped positionless prospect and begged them to sell him on him when the roster was a Skubal away from doing potential October damage. Alas, those days are gone and they’re not coming back.

Why Now?

So with the two-headed monster of Elibernaz (actually, let’s be real, it’s Albi-ass) coming back, and another Holliday offseason and/or spring training cut short due to surgery (pending wrist procedure) and him slight and brittle and unable to turn his natural speed into any kind of weapon and with him downright deficient at second base, he has to go.

With Jordan Westburg coming back from his latest surgery, and him brittle and not durable, but with a legit run-production profile this lineup desperately needs, he will be given every chance to bounce back. And at this point, I’m simplifying his program – Westburg is a second baseman. Less strain on the body there. Let’s get 120 games out of him there and some DH work.

Because we also know Elias is going to be all about Christian Encarnacion-Strand in 2027, loving to try to turn a AAAA guy into a regular, and with CES’s power productivity and the glove playing better than expected, he is in the mix. And Pete Alonso and Samuel Basallo block first base. Coby Mayo was the one young player who truly exceeded expectations on this roster, and he kills left-handed pitching and you can live with the glove at third once or twice a week.

And Gunnar Henderson is not an MLB shortstop and he won’t be here past the trade deadline and he could be dealt this winter (and they don’t have the guts to move him to third, where he’s always belonged). If he is dealt before the lockout, Blaze Alexander would be an option at short, and they should go get a glove-first shortstop anyway and stop running fake teams out there with no spine. Either way, Elias will want Alexander to play a lot, so you tell me where Holliday fits in?

What About Selling Low?

Toronto Blue Jays left fielder Charles McAdoo (26) steals second base as second baseman Jackson Holliday (7) misses the throw — Sep 13, 2026; Toronto, Ontario, CAN; Toronto Blue Jays left fielder Charles McAdoo (26) steals second base as Baltimore Orioles second baseman Jackson Holliday (7) misses the throw from catcher Samuel Basallo (not pictured) during the second inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | IMAGN IMAGES via Reuters Connect

Never stopped Elias before, it’s another specialty of his, and it could always get worse. In Birdland, it always does. That's The Elias Way.

Holliday has too many voices in his head, and yet another new hitting staff that is surely on the way here as Elias scapegoats middle managers while being a 100% fraud himself, will only make it worse. I’m thinking his daddy is ready for him to have a fresh start (with a team further from alleged contention than the Orioles) and agent Scott Boras is ready for him to have a fresh start, where the pressure of being the overhyped 1-1 won’t matter as much.

We won’t belabor the point defensively, because it’s ugly all around and the instincts at 2B are not natural or fluid. He is 20th among all MLB players with at least 500 innings at second in fielding run value. He is in the 88th percentile in sprint speed and played nearly 100 games this season and had eight steals and got thrown out three times; in an era where they made stealing bases easier than ever, he has 29 steals to 14 times caught stealing for his career.

Abject failure they couldn’t fix this, but a smart organization probably can.

As for the hit tool, man, it’s still a mess. You could tell me he’ll still only be 23 by spring training, but he has 1100 MLB plate appearances and he’s also been in this org five years now and he is going backwards, rapidly. Injuries or not, he had a .640 OPS this season and he was 17 percent worse than the average MLB hitter (OPS+) … those are below his career totals (.654 OPS and 86 OPS+).

Holliday stopped swinging as hard and moved off the plate in the box and changed his swing plane in an effort to get on base more and work the ball between the gaps .. and ended up with a .300 OBP, much worse than last year, and a .229 average, also much worse than 2025. And really, the fact he ends the season on the IL like he began it, needing yet another procedure, kind of says it all.

He is a number nine hitter in a real MLB lineup, and I’m not sure where he plays most of the time. They gave him another run at the top of the lineup when he was hot in July, and that leadoff stint was largely a disaster (.267 OBP and .614 OPS). He had an amazing July, and arguably in every other month he looked like someone who needed more seasoning in AAA.

Holliday had a .582 OPS in 50 games at Camden Yards, a park that should suit him from the left side, and a .601 OPS in the second half of the season. It’s over here.

Sadly, it never even ever really got going here, and worst of all, the guy who created this problem is still the one charged with fixing it.

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