Orioles Gunnar Henderson Must Move To Third Base In 2027 (And Jackson Holliday To OF)

Most smart baseball people who have pondered Gunnar Henderson’s future in Baltimore have come to the conclusion that he isn’t long for here.

With Adley Rutschman, the only player Orioles failed baseball exec Mike Elias drafted before Henderson, just dealt to a contender with two years of team control left and no hope for a contract extension here, the same is expected for Henderson. Henderson’s agent, Scott Boras, doesn’t do extensions this deep into a player’s career and the agent surely harbors the same reservations about the Orioles’ broken player development department as the rest of the industry does.

But there’s a chance the new labor rules impact Henderson’s situation somehow, perhaps the owners are successful in getting a franchise tag of sorts like football has that could teether Henderson here. Or more likely, the front office tries to get Henderson going next season and deals him closer to the trade deadline with hopefully more value attached.

Regardless, one option that absolutely must be strongly considered is moving him to third base. Under any circumstances. Immediately after the season.

Whether third baseman Jordan Westburg comes off elbow surgery and is great back at the hot corner, or not. This franchise needs to totally rebuild its outfield, it must strongly consider moving Jackson Holliday to centerfield, and if they want to get serious about returning to The Oriole Way, they must find an elite veteran defender to man shortstop and strengthen the spine of their defense next year (in the way Jose Iglesias did early in the rebuild).

The more I thought about this the more paramount it seems, and longtime MLB exec Jim Duquette – a former Orioles decision-maker who watches them very closely – agreed completely as will be featured on “The Daily Flock Show” on Thursday. Gunnar needs to go to third (if he stays in Baltimore), a real glove-first shortstop must be brought it, and Holliday needs to given an offseason assignment to learn the outfield.

“They need a better defender at shortstop,” Duquette concurred. “I think we’ve seen enough of Gunnar, and he profiles better as a third baseman … He’s just not consistent enough as a defender …

“Most organizations are built around good pitching, good behind the plate and good up the middle and in centerfield, defensively. And the Orioles are one of the few teams that aren’t in that area … You don’t have to spend a lot of money to get a good defensive shortstop and move Gunnar to third and move Westburg to second and maybe move Jackson to the outfield.”

Preach.

A Different Approach

The Orioles have always wanted to throw more at Henderson – who has an OPS below .700 since the 2025 All-Star break and has been an error machine as well – with him working harder and trying harder. But more isn't always better and this coaching staff clearly has never reached him or connected with him and he looks more lost by the day and has been totally sapped of his ability to drive in runs (22 on the road all season, and that's just for starters).

They don’t give him enough time off, or mental respites, and they have forced the shortstop thing to the point where Duquette and others I’ve talked to – like former GM Dan O’Dowd - think it’s pulling down his overall production and profile. Among all MLB shortstops to play at least 200 innings since the start of 2025, Henderson ranks 35th in fielding run value, and not even his range rates as above average let alone his accuracy or overall profile (and his instincts and approach to double plays keeps regressing.

Getting away from the Orioles staffers – and their launch-angle fascinations – could perhaps Henderson course correct this winter with help from Boras and his personal facility and trainers, as well as facilities like Driveline. The Orioles have gone through three coaching staffs now, handpicked by failed baseball exec MIke Elias, who could not improve infielders or outfielders.

“Scott is really, really good at helping his players get better,” Duquette noted, “whether in season or out of the season. That’s going to have to be an overhaul. There’s an awful lot of swinging underneath pitches and trying to launch balls and hit home runs, and this has been going on for two years now.”

Duquette agreed whole-heartedly with O’Dowd, that the Orioles need to get people back in the org who understand fundamentals and can teach it, and that it must be a franchise priority to try to get Henderson and Holliday to positions where they might be able to shine more in the field and at the plate.

“I do think Holliday is a good enough athlete that he can play centerfield,” Duquette said. And, like me, he prefers Westburg at second base, where Holliday plays now.

The full conversation with Duquette - which covers a comprehensive plan to try to improve Birdland - will be available at www.youtube.com/@BIGPLAYBaltimore. A full dissection with O'Dowd, who ran the Orioles farm system in the 1980s, is below.

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