Jackson Holliday’s future with the Orioles may end up being tied less to second base and more to center field.
That’s where the conversation is heading as Baltimore tries to sort through a roster full of problems and an organization many around the league believe can’t fix them if Mike Elias stays in charge of baseball operations. Whatever happens at the top, Holliday still has to keep building on the progress he showed in the second half of 2026 and carry that into 2027. The bigger question is where he’ll be doing it.
Second base has not come naturally enough to lock him in there, and the old shortstop dream is gone. His arm, as has long been understood, won’t support that kind of move. But longtime MLB general manager Dan O’Dowd sees another path for the former first-overall pick, one that lines up with the idea Joe Sheehan raised on "The Daily Flock Show,".
O’Dowd 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.”
There’s a case for letting him keep sharpening his game somewhere warmer than Baltimore, too. Winter ball would make sense, especially for a team that has largely dismissed that kind of development path under Elias. Rookie Samuel Basallo, who just turned 22 and again didn’t catch much this season after only 200 games there in the minors, is another example of why that approach could help.
The roster picture only adds to the argument. Holliday missed about the first 50 games because of a broken hand, and the infield could get crowded fast.
Blaze Alexander may be on track to become an everyday infielder and should return soon from a broken hand. Jordan Westburg is coming back in 2027 from elbow surgery.
And if Gunnar Henderson isn’t moved quickly, even though he probably will be, that complicates things further.
Baltimore also has a glaring problem in center field. It does not have anything close to a true everyday answer there.
Colton Cowser is barely a fourth outfielder, and this front office clearly doesn’t view former first-round pick Enrique Bradfield Jr. or AAA addition Christian Franklin as players who have passed him on the depth chart. The free-agent market offers little help, and finding a real major league center fielder via trade is easier said than done.
That leaves Holliday as a logical possibility.
If he isn’t the answer in center, someone else has to be. And if Henderson sticks around until near the 2027 trade deadline, assuming labor unrest doesn’t wipe out that timing, then a defensive alignment of Henderson at short, Alexander at third and Westburg at second would give Baltimore its best infield setup by a wide margin.
For now, the Orioles are still stuck waiting on a rebuild that hasn’t delivered. And unless the front office changes, there’s a growing sense that the people left to sort it out may not be the ones best suited for the job.
In Other News...
Gunnar Henderson Has Become A Worrying Sign For The Orioles
Gunnar Henderson has been one of the faces of the Orioles young core, so any hint of regression lands with extra weight in Baltimore. MLB Network analyst Dan ODowd recently raised alarms about Hendersons direction, pointing to a decline in both his hitting and defense since the 2025 All-Star break and framing it as more than a temporary slump. For a team built around internal development, concerns like that naturally spill beyond one player and into the broader question of how the Orioles are shaping their talent.
ODowd went a step further by suggesting the organization, under Mike Elias, may not be getting the most out of Hendersons ability. He even floated the idea that the shortstop could be traded by 2027, while also recommending changes to the developmental setup, including bringing in Bill Ripken as an infield coordinator and perhaps involving Buck Showalter in some role. Whether Baltimore takes any of that seriously is another matter, but the conversation underscores how important Henderson remains to the franchises future and how quickly expectations can shift when a cornerstone player starts to look off track. [Read more 🡒]
Gunnar Henderson Might Finally Have The Fix Orioles Fans Needed
Gunnar Hendersons recent slide had become one of the quieter concerns around Camden Yards, especially for a lineup that leans on him to help set the tone. So the sight of Pete Alonso spending time with Henderson in practice, working through batting mechanics and zeroing in on lower-half posture and hip stability, offered a different kind of development for Orioles fans to track. It is the sort of behind-the-scenes tweak that can matter as much as any box score, particularly when a young hitter is trying to regain the timing that made him one of the clubs most important bats.
What makes the collaboration notable is the source of the advice, with Alonso drawing on his own experience to help Henderson sort out the issues that have made fastballs such a stubborn problem this season. Henderson has shown signs of improvement lately after the prolonged slump, but the work points to a more specific fix than a simple hot streak. For Baltimore, the appeal is obvious: if the changes hold, the Orioles might finally be getting closer to the version of Henderson they have been waiting for. [Read more 🡒]
Orioles Prospect Suddenly Has A Real Shot To Fill Key Bullpen Need
Luis De Len has become one of the more interesting arms in the Orioles system this summer, and not just because of his prospect status. Baltimore is moving him into a relief role at Triple-A Norfolk, a shift that gives the organization a chance to see whether his stuff can translate quickly to a bullpen setting and possibly help fill a need later in the season.
De Len already made his first relief appearance recently, and he has impressed in both Double-A and Triple-A this year, which is why the transition is worth watching closely. Manager Craig Albernaz has been upbeat about De Lens talent and what he could bring to the club, and if the adjustment keeps going well, the Orioles may have found a candidate for the bullpen without having to look far outside the system. [Read more 🡒]