Orioles Unlikely to Sign Gunnar Henderson to Extension, Says Rosenthal

MLB insider Ken Rosenthal believes the odds of the Orioles signing their star player to a new contract before free agency are extremely low.

Mar. 31, 2026 at 8:19pm

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A fractured, multi-perspective painting depicting a baseball player's motion broken down into sharp, overlapping geometric shapes in vibrant colors, conceptually representing the complexities of contract negotiations in professional sports.The Orioles' struggle to retain their star player Gunnar Henderson reflects the challenges small-market teams face in keeping top talent.Today in Milwaukee

According to The Athletic's Ken Rosenthal, the Baltimore Orioles are unlikely to sign star player Gunnar Henderson to a contract extension before he hits free agency in two years. Rosenthal cites Henderson's representation by agent Scott Boras as a key factor, as Boras typically prefers his clients to test the open market rather than sign below-market-value extensions.

Why it matters

Henderson is one of the Orioles' top players and a key reason they have a chance to make the playoffs in 2026. If the team cannot sign him to an extension, they may have to consider trading him before he hits free agency to get value in return.

The details

The Orioles spent money this offseason to improve their roster after a disappointing 2025 campaign, signing players like Pete Alonso and trading for and extending Shane Baz. However, Rosenthal believes the odds of the team signing Henderson, who will turn 26 this season and has two years of arbitration left, to an extension are 'extremely low.' Rosenthal notes that while the Orioles could theoretically offer Henderson a massive $250 million deal, it is unlikely they would be able to get such a deal done given Henderson's representation by Scott Boras, who generally prefers his clients to test free agency.

  • Henderson will turn 26 this season.
  • Henderson has two years of arbitration left before hitting unrestricted free agency.

The players

Gunnar Henderson

A star player for the Baltimore Orioles who is set to hit free agency in two years.

Scott Boras

The agent who represents Gunnar Henderson and is known for preferring his clients to test the open market rather than sign below-market-value extensions.

Cooper Pratt

A Milwaukee Brewers prospect who is also represented by Scott Boras.

David Rubenstein

The new owner of the Baltimore Orioles who spent money this offseason to improve the team's roster.

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What they’re saying

“The question is whether Gunnar Henderson would sign an extension below market value, because that's what these things generally are. He is represented by Scott Boras. Scott Boras also represents [newly-signed Milwaukee Brewers prospect] Cooper Pratt, and from that perspective alone, the extension for Pratt is surprising. Because Boras in general prefers his clients to go to the open market.”

— Ken Rosenthal, MLB Insider

“I would say the odds of the Orioles signing Gunnar Henderson are extremely low. Now they could offer him $250 million tomorrow, leak it, and say 'We Tried!' But we all know it's not going to be easy for them to, one, make that offer, and two, get it done at that number.”

— Ken Rosenthal, MLB Insider

What’s next

The Orioles will have to decide whether to trade Gunnar Henderson before he hits free agency if they cannot sign him to an extension.

The takeaway

This situation highlights the challenges small-market teams like the Orioles face in retaining their star players, especially when they are represented by high-profile agents like Scott Boras who typically prefer their clients to test the open market.