Orioles may turn Gunnar Henderson dip into shocking offseason win

The Baltimore Orioles may be trudging through one of their most disappointing seasons in recent memory, but the franchise still has a chance to make a statement that echoes far beyond 2025. If there’s one move that can flip the narrative from frustration to hope, it’s locking up Gunnar Henderson with a long-term extension this offseason.

For a fan base that has endured setbacks, ownership questions, and a roster shuffle that hasn’t lived up to expectations, an extension for their star shortstop would be the clearest message yet: the Orioles are serious about building a winning future.

That’s the crossroads Baltimore now stands at. Henderson has been vocal about wanting to play for a “winning culture,” something Baltimore hasn’t delivered in full. Signing him would do more than keep a franchise cornerstone in orange and black — it would restore faith in fans who desperately want to believe this young core can deliver championships. But there are hurdles.

Orioles have perfect chance to extend All-Star shortstop Gunnar Henderson after down year

Henderson is represented by Scott Boras, an agent notorious for pushing his clients to test free agency. Combine that with a season where the Orioles failed to contend and Henderson endured a dip in production, and the path to an extension becomes complicated. Still, if Baltimore plays this right, Henderson’s down-year could create a rare window of opportunity to lock him up at a price that won’t balloon out of reach.

There are signs the organization may finally be ready to take that leap. President of Baseball Operations Mike Elias already made waves with the extension of Samuel Basallo, framing it as the first domino in a larger commitment to securing the Orioles’ young stars. Henderson is the next logical piece. The message to both him and the fans would be clear: the Orioles are not just waiting for the future, they’re investing in it now.

Other teams have set the precedent. Look no further than the Seattle Mariners, who locked up Cal Raleigh with a six-year, $105 million extension earlier this year. That deal wasn’t just about securing a cornerstone catcher, it was about proving the organization was serious about surrounding him with talent. They backed that promise by trading for impact bats like Josh Naylor and Eugenio Suárez, and now the Mariners are neck-and-neck with the Astros in the AL West race. The player got his security, the team got its leader, and the fans got proof of a winning vision.

The Orioles should be paying attention. Henderson is more than just their best player, he’s the kind of talent that defines eras, the type you build a roster around for a decade. Signing him now, even at a slight discount due to his dip in production, could be the most impactful move Baltimore makes all winter. And for a team looking to prove that “trusting the process” isn’t just empty words, it might also be the most necessary one.

Because while seasons come and go, cornerstone players like Gunnar Henderson don’t. The blueprint is there, the window is open, and the Orioles have a golden chance to shock the baseball world by proving they’re ready to build something that lasts.

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