Jackson Holliday Could Be The Answer To The Orioles 2027 Centerfield Question

The Orioles have myriad issues they need to fix as an organization and many around the league believe they have almost no chance to correct them if Mike Elias remains in charge of baseball operations.

Regardless of who is in charge, former first-overall pick Jackson Holliday must continue to develop and try to carry over the strides he has made in the second half of 2026 into 2027. The question of where he does that from – as in what position he plays – is up for debate with him not taking all that naturally to second base, and add longtime MLB general manager Dan O’Dowd to the list of those who has major issues with O's player development but thinks he could be an asset in centerfield.

Holliday is an elite athlete with premier speed and twitch, and while his arm will never allow the dream of playing shortstop to be a reality – even though Elias hyped him as such through his minor league career – that will never be the case. But O’Dowd, like us, is buying some of the fundamental changes Holliday has made at the plate, and believes, like analyst Joe Sheehan suggested on "The Daily Flock Show,", that centerfield isn't too tall an ask.

O’Dowd, who worked in the Orioles front office as an entry-level staffer when they last won the World Series in 1983 said: “Do I think Jackson could play centerfield? I mean Al Bumbry (starting CF on that 83 team) played centerfield with what, a three arm? He couldn’t throw from here to the end of my office, and so, yeah, you can play centerfield with a below average arm.

“But I think there is so much more in Jackson. I don’t think he’s come close to hitting his ceiling. And I think he’s going to be an impact player at the big-league level. I think he’s going to hit home runs. I just think he got rushed and now it’s been a period of regrouping at the big-league level, and I just think he is beginning to find his stride and I think he’s going to be fine.”

Start The Process In Winter Ball?

Spending time in winter ball would make a lot of sense. Elias has basically scorned this for the entirety of his organization, but with rookie Samuel Basallo, who just turned 22 and did not catch a ton yet again this season after just 200 games there in the minors, it could really help.

Holliday missed roughly the first 50 games of the season with a broken hand, and with Blaze Alexander potentially an everyday infielder (he should be back from a broken hand soon enough) and Jordan Westburg back in 2027 from elbow surgery, especially if Gunnar Henderson is not quickly deal (he probably will be), all the more reason why outfield should be in play.

The Orioles lack anything close to an everyday centerfielder. Colton Cowser is barely a fourth outfielder and this regime clearly doesn’t think anything of former first-round pick Enrique Bradfield Jr or AAA acquisition Christian Franklin wouldn’t have passed him by on the depth chart. The free agent class stinks and trading for a real MLB centerfielder is easier said than done, so Holliday would make a lot of sense there.

If Holliday isn’t the solution in center, someone else better be.

If Henderson isn’t dealt until closer to the 2027 trade deadline (assuming there is one with labor unrest ahead), then him at short (with his flaws) and Alexander at third and Westburg at second would be the best defensive infield for Baltimore, by far. With any luck, someone other than Elias will be sorting through what’s left of this failed rebuild.

But given the private-equity goals of this ownership group, beyond anything we’ve seen in terms of true ambitions to win in October, it’s hard to think David Rubenstein will do the right thing.

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