Orioles Unlikely to Extend Gunnar Henderson Anytime Soon

MLB Insider Ken Rosenthal casts doubt on the team's chances of signing the young star to a long-term deal.

Mar. 31, 2026 at 10:10pm

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According to MLB Insider Ken Rosenthal, the Baltimore Orioles are unlikely to sign star shortstop Gunnar Henderson to a contract extension in the near future. Rosenthal cited Henderson's representation by agent Scott Boras, who typically prefers his clients to reach free agency, as a major obstacle to a deal getting done. The 24-year-old Henderson is coming off an impressive 2023 season in which he won AL Rookie of the Year and made his first All-Star team.

Why it matters

Keeping homegrown talent like Henderson is crucial for the Orioles as they look to build a sustainable contender in the tough AL East. However, Boras' negotiating style and Henderson's impending free agency at age 26 make an early extension a long shot, potentially forcing the team to wait until closer to his free agency to try to lock him up long-term.

The details

Henderson, who was promoted to the majors late in the 2022 season, had a breakout 2023 campaign, winning Rookie of the Year and making the All-Star team. He is represented by agent Scott Boras, who is known for preferring his clients to reach free agency rather than signing extensions. Rosenthal believes the Orioles would likely have to offer Henderson a massive contract, potentially in the $250 million range, to have any chance of signing him to an extension before he hits free agency in two years.

  • Henderson was named AL Rookie of the Year in 2023.
  • Henderson made his first All-Star team in 2024.
  • Henderson will become a free agent at age 26 after the 2025 season.

The players

Gunnar Henderson

A 24-year-old shortstop for the Baltimore Orioles who was named AL Rookie of the Year in 2023 and made his first All-Star team in 2024.

Scott Boras

A prominent MLB player agent who represents Gunnar Henderson and is known for preferring his clients to reach free agency rather than signing contract extensions.

Mike Elias

The president of baseball operations for the Baltimore Orioles.

Craig Albernaz

The first-year manager of the Baltimore Orioles.

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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 Cooper Pratt [newly signed prospect of the Milwaukee Brewers], 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 likely have to wait until Henderson is closer to free agency in 2025 to have a realistic chance of signing him to a long-term extension, unless they are willing to offer him a record-breaking contract that Boras and Henderson would be willing to accept.

The takeaway

Keeping homegrown stars like Gunnar Henderson is crucial for the Orioles as they look to build a sustainable contender in the tough AL East. However, Henderson's representation by Scott Boras and his impending free agency make an early extension a major challenge, potentially forcing the team to wait until closer to 2025 to try to lock him up long-term.