Ask anyone in the industry with knowledge of the Orioles’ approach to the trade deadline and one word is bound to enter the conversation.

“Complicated.”

The Orioles aren’t alone when it comes to the uncertainty over buying, selling or doing a little of both. The mediocrity in the American League teases more teams into believing that they can grab a Wild Card spot. To surrender while only a handful of games out of the picture isn’t an easy maneuver, and it’s definitely a hard sell for fans.

The same haze didn’t envelop the Orioles at the 2025 deadline. Their intentions were clear. They strictly sold and tried to restock the farm system.

They were frenzied buyers in 2024 despite trading Austin Hays to the Phillies, acquiring Zach Eflin, Trevor Rogers, Seranthony Domínguez, Gregory Soto, Eloy Jiménez and Austin Slater. They were calm buyers in 2023, acquiring starter Jack Flaherty and failing to get much out of him.

The media felt the same way when trying to interview him.

The teardown in 2018 signaled the beginning of an ugly rebuild, with former executive vice president Dan Duquette trading Manny Machado, Kevin Gausman, Darren O’Day, Zach Britton, Brad Brach and Jonathan Schoop. Every deadline until 2023 had the Orioles selling.

The current situation reminds me a little bit of the predicament in 2017. Rumors swirled that the Orioles would raise the white flag and trade Britton and Brach, among others, but they shocked the industry and the local media by acquiring starter Jeremy Hellickson and infielder Tim Beckham. The front office strategy was a mystery until the end, which is the only reason why I’m bringing up that summer.

The Orioles sent outfielder Hyun Soo Kim, minor league pitcher Garrett Cleavinger and future considerations to the Phillies for Hellickson. They needed a starter like so many other teams in a thin market, but surrendering Kim still raised questions about their motivation.

Beckham was the stunner, going from the Rays to the Orioles just before the deadline for minor league pitcher Tobias Myers. A common reaction went something like this: “What are they doing?” And also, “What was the point here?”

The answer, of course, was buying in order to make the playoffs despite the slim odds. But they weren’t aggressive. Hellickson and Beckham couldn’t move the needle much. They were upgrades, but not real difference-makers.

The window of contention was slamming shut and Duquette tried to prop it open just a little while longer.

“We picked up a couple of starting pitchers and a shortstop. And we’re gonna take a shot at getting the most out of this season,” Duquette said shortly after the deadline.

“I mean, nobody is running away with the American League East. Teams are so evenly matched. If you make a move here or there and it jells, I mean, who knows? We still have some hope that we can make the playoffs.”

The difference in 2026 is that president of baseball operations Mike Elias figures to make bolder moves. He could trade players on expiring contracts, including Taylor Ward, Trevor Rogers and Andrew Kittredge, and others with free agency further down the road. Naturally, he’s listening to offers for any of his players, which isn’t the same as shopping them.

Elias also could add controllable players who are expected to assist in the playoff push, which, I’ll say again, is complicated if he’s subtracting guys like Ward and Rogers. That’s mostly in, but not all in, right?

In that regard, it’s harder to find an Orioles deadline comp.

None of this is fresh information. The possibility of blurring buy and sell has been stated for a while, and the needs are defined – starter, left-handed reliever and perhaps a right-hander, and a right-handed bat for the outfield. They might be done with catcher after yesterday’s trade for Jake Rogers.

Adley Rutschman is the fascinating figure. Scouts and other talent evaluators from opposing teams confirm that Elias seems more willing to trade the three-time All-Star catcher, but again, that isn’t aggressively trying to move him. Rutschman has one more season before free agency. It’s doubtful that any extension talks, assuming they exist, have gained traction. So check the offers and see whether the return could make a significant impact this season, as well as in future years.

The downside of course is breaking up the Rutschman/Samuel Basallo tandem that separates the Orioles from other clubs. That’s a special pairing. That’s placing a lot of trust in Basallo to stay healthy and be the workhorse behind the plate. And Rutschman’s defensive work has been exceptional.

I won’t believe that Rutschman is going to be traded unless news breaks. Then, I’ll believe it.

Here are a few mailbag leftovers while waiting for any news to break.

108 games into the season and we still have Gunnar in the 1-3 holes. Any idea why management hasn’t decided to take some pressure off him and lower him in the lineup? Also, what’s the new fascination with Ward in the 4 hole vs RHPs? A guy with a .390 on base and .350 slug seems to be a better fit at leadoff.
Having Adley Rutschman and Samuel Basallo on the injured list is forcing some changes to the lineups. We’ll start there. But yeah, Ward leading off with his 2026 on-base percentage makes sense atop the order. The Orioles haven’t given up on Henderson going on a hot streak. They’re banking hard on it. There’s definitely an argument for lowering him if the team has better options for the top four spots. Does it?

Roch, with the bullpen looking increasingly heavily taxed and dealing with recent injuries, how sustainable is this current usage down the stretch?
The ‘pen has been one of the biggest surprises, which is quite a leap from biggest concern, but the Orioles need reinforcements. They could use a high-leverage lefty. An opposing coach complimented the unit but questioned whether the results were sustainable. As you’re doing. I’ve heard the same from some scouts. And Elias could punch some holes in the ‘pen. Other teams are checking on the club’s relievers and Elias might be willing to move Kittredge or Yennier Cano, to name two.

Why was Hans Crouse released? Asking for CB Coach.
I’m sure he appreciates it. CB is the reason why I asked about Crouse’s lack of usage in camp. The Orioles needed the roster space with a recent wave of promotions to Triple-A Norfolk, and they must not have viewed Crouse as a piece moving forward. His past health issues might have been a concern.

If I set the over/under for Orioles’ trades before the deadline at 2.5, what are you taking?
The over, without question.

Why was Jackson Holliday on the bench against Tarik Skubal when he’s been the hottest hitter on the team?
Manager Craig Albernaz explained it to the media, saying it wasn’t strictly a lefty-lefty decision, but “it’s a little different animal with Tarik Skubal.” He isn’t wrong. Here’s the rest of Albernaz’s quote: “Seen him for two years and what he’s done. And also, it’s a byproduct of Holliday was playing a lot, which is great, and it gets (Jeremiah Jackson) in there as well.” Holliday came off the bench and had two hits and three RBIs. It worked out.

Which of our top prospects would you not trade? Who on the current 26-man roster are untouchables?
Anyone in the system should be on the table in the right deal. I know the risks. The Orioles could regret parting with, say, a healthy Nate George and Ike Irish, or Joseph Dzierwa, Caden Hunter, Wehiwa Aloy and Luis De León. I’d be uncomfortable pulling the trigger, but how can you say “no” without hearing the return? I cringed when the Orioles included catcher Caden Bodine in the Shane Baz deal with the Rays, but it happened. As for the active roster, I’ll give you the obvious one, even though he’s on the injured list: Samuel Basallo. I heard it from a couple of scouts. That’s a nonstarter, as you’d expect. And yes, I veered from your actual question and named someone who isn’t currently on the 26-man roster. Forgive me. I’ve also heard that they aren’t trading Jackson Holliday, but it doesn’t stop teams from asking about him. That’s how it works.

MLB Pipeline updated each team’s Top 30 prospects a few days ago. Why didn’t it include Eric Booth Jr.
or any of the other signed draft picks, especially when other publications ranked Booth Jr. among their Top 100 prospects?

Check back with them in August for their full re-rank. In the meantime, this is what I was told by someone at MLB.com: “They only updated the team Top 30s to have prospects in more accurate spots ahead of the trade deadline, because so many prospects will get traded and it gives a better representation of what teams are acquiring.” Yeah, I went to that much trouble to find your answer because that’s what I do.

Buy? Sell? Some of both? Stand pat? Just trade expiring contracts?
Me or the team? Some of both. They aren’t standing pat and they aren’t focused only on pending free agents. We were led to believe last summer that they’d only move expiring contracts, and then they traded Bryan Baker, Andrew Kittredge, Ramón Laureano and Ramón Urías.