The Orioles are once again asking their fans to trust the long game, and that comes with a familiar warning label.
At this year’s trade deadline, Baltimore moved fan favorite Adley Rutschman to the Boston Red Sox and came away with what looks, on paper, like a serious return: pitchers Anthony Eyanson and Kyson Witherspoon, plus outfielder Enddy Azocar. All three immediately showed up in MLB Pipeline’s Top 10 prospects in the Orioles’ minor league system. For a club weighing whether it could afford to keep Rutschman on a long-term deal, that’s the kind of haul front offices dream about.
But Orioles fans have seen a version of this movie before, and it did not end well.
A resurfaced Jeff Passan tweet from 2018 laid out the scale of Baltimore’s previous deadline purge, when the team traded away Manny Machado, Jonathan Schoop, Kevin Gausman, Zach Britton, Darren O’Day and Brad Brach. In return, the Orioles collected 15 players, 14 of them minor leaguers.
“The Baltimore Orioles nuked their major league roster, trading Manny Machado, Jonathan Schoop, Kevin Gausman, Zach Britton, Darren O’Day and Brad Brach. In exchange, they received 15 players - 14 of whom are minor leaguers. Here’s the haul for a quarter of their big league team. pic.twitter.com/fGBRHPFlsp”
That 2018 sell-off was understandable in the moment. Many of those players were on expiring deals, and Baltimore extracted a hefty volume of talent. The problem is what came next: after eight years, the Orioles were left with a return that amounted to almost nothing.
The Machado deal is the one that still draws the sharpest criticism. Of the five players Baltimore got from the Dodgers, only Dean Kremer provided real value, and even that was as a solid, not star-level, arm for several seasons. The rest disappeared quickly, and the Orioles were short on MLB-ready help until 2022.
This season’s deadline strategy fits a different Baltimore team, though not one without its own tension. The organization has rebuilt its farm system and still has a strong young core in the majors.
It has spent the past few seasons knocking on the door of contention, only to come up short. That pushed GM Mike Elias and the front office to pivot toward 2027 and deal away players like Rutschman, Tyler Wells, and Taylor Ward.
That’s the gamble: a seller with plenty to offer can still lose big if the prospects don’t hit. Eyanson and Witherspoon could become rotation pieces.
Azocar, who is 19, has already impressed scouts with tools that could play in the majors. But none of that changes the reality that Baltimore is trading certainty for possibility.
As of Aug. 18, the Orioles are holding the final AL Wild Card spot, so a late charge is still on the table. But the larger picture is already clear.
The club has made it obvious that 2026 is no longer the top priority, and fans are being asked to live with that choice. After what happened in 2018, they have every reason to be wary of another deadline that looks smart now and painful later.
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