Key upcoming stretch could determine Orioles' Trade Deadline strategy

BALTIMORE -- The first half of the Orioles’ 2026 season was largely disappointing. They came into the year with big expectations, as did their fans. They believed they’d be a top team, and instead, the past 3 1/2 months have been filled with plenty of inconsistency and frustration.

Yet, Baltimore comes out of the All-Star break only two games out of a playoff spot.

That’s right. It may feel like the O’s haven’t played like a contending team -- and everybody on the team would agree with that statement -- but they’re in the thick of a crowded American League Wild Card race. And they may finally be making the type of push they’ve been striving for, as they closed out the first half with a season-high four-game winning streak.

• Record at the break: 46-51 (Fourth in AL East, 11 1/2 games back)
• Record at the break last year: 43-52 (Fifth in AL East, 11 1/2 games back)
• Playoff odds: 21.6% (per FanGraphs)
• Remaining strength of schedule: .506 (Ninth-hardest in MLB, per Tankathon)

“I’m confident in this group that it can put together a really good run,” infielder Coby Mayo said. “With the American League wide open, it takes one good run to be right back where you want to be. We’ve got a lot of games left, and I think there’s absolutely no time to panic.

"I think this team has not played anywhere close to the best baseball we can, and this is the type of team that can go on a run.”

What this all means is that this is shaping up to be a critical Trade Deadline for the Orioles.

Will they go all in and buy? President of baseball operations Mike Elias expressed his desire to do that in late June, and Baltimore has stayed in the race since.

Could the O’s still sell? They have 15 games to play before Aug. 3, so nothing can be completely ruled out at this point.

Maybe the Orioles will do a little of both, much like in 2024. They added several big league players at the Deadline that year (including starters Zach Eflin and Trevor Rogers), but they also dealt outfielder Austin Hays to the Phillies in order to bolster their bullpen and acquire right-hander Seranthony Domínguez.

It shouldn’t be like 2025, though, when Baltimore traded nine big leaguers in exchange for 15 prospects in a Deadline fire sale. It would take quite a collapse over the next 2 1/2 weeks for the O’s to even consider a substantial sell-off.

Let’s dive deeper into where the Orioles stand with the All-Star break nearly over and the Trade Deadline looming in the not-so-distant future.

Biggest need
If the O’s intend on buying and making a legitimate run at the postseason, they need to upgrade their bullpen. Closer Ryan Helsley (right elbow inflammation) is going to miss a bit of time and may not start throwing until August. Their left-handed options have also taken a hit with Keegan Akin sustaining a UCL injury that could sideline him for quite a while.

Baltimore can’t fully bank on All-Star closer Félix Bautista (right shoulder surgery), but if the 31-year-old right-hander can return in September, his presence could certainly help. Still, the Orioles could use at least one or two relief arms.

It can never hurt to add a quality starting pitcher. And perhaps the O’s would now be in the mix for infield depth after losing utility man Blaze Alexander to a left hand fracture.

Biggest chip
Would the Orioles consider trading any of their three Top 100 prospects (outfielder Nate George, outfielder/first baseman Ike Irish or left-hander Joseph Dzierwa)? They might have to move one if they want to make a huge splash. But there are some other strong pieces in the farm system that could be viable chips, likely more on the pitching side.

If Baltimore makes any seller-type moves, it would be most likely to trade players on expiring contracts, such as Rogers or outfielder Taylor Ward.

Key player for second half
Gunnar Henderson, without a doubt. The 25-year-old star shortstop has had a challenging season thus far, hitting .224 with a .697 OPS through 96 games. His power has still been there (17 homers, which ranks second on the team), but his level of play has been down from the first three full seasons of his MLB career.

Henderson may be turning things around, though, as he went 5-for-13 (.385) during last weekend’s three-game sweep of the Royals, finishing the series with a three-hit performance on Sunday. If he can keep it going, it would be a huge boost for the O’s moving forward.

Determining factor
The O’s open the second half with a six-game road trip through Houston and Boston, and both the Astros and Red Sox are among the teams between the Orioles and the third AL Wild Card spot. How Baltimore fares on that swing could heavily impact the club’s Trade Deadline plans.

If the O’s can build on their four-game win streak and come out of the break hot, their season could potentially take off from here.