Gunnar Henderson is showing the Orioles the risks of giving him long-term extension 

Just two seasons ago, it seemed like it was a guarantee that the Baltimore Orioles would try everything in their power to sign Gunnar Henderson to a long-term extension. After all, he was one of the rising superstars in the game and a player that fans assumed would be a perennial MVP candidate. Many predicted that Henderson was in the perfect position to rake in a contract worth well more than $300 million. 

According to Jon Heyman of the New York Post, the Orioles reportedly offered Henderson a contract extension ahead of the 2026 season. While it’s not clear how much that offer was worth, it’s a safe bet to assume it was a decent chunk of change. So betting on himself to increase his value, Henderson eyed a strong year to prove that he was worth being made one of the highest-paid players in baseball.  

That strong year did not happen for the shortstop, especially down the stretch. As we take a step back and review the disappointing 2026 season for the Orioles, many fans are pointing to the regression of Henderson as one of the biggest factors in the team’s under-performance. That wouldn’t even be that far-fetched considering that Henderson’s offensive production has taken a substantial nosedive since his impressive 2024 season. 

At just 25 years old, it’s obviously way too soon to say that Henderson won't be able to find his swing again and get his OPS back over .800. Besides, his 3.6 fWAR season in 2026 is nothing to scoff. That still ranked as the 9th highest fWAR for a shortstop in all of baseball. But with Henderson approaching free agency in 2029, we are now entering the prime time to start discussing what a potential contract extension could look like for him. 

Is a .715 OPS in 2026 good enough to justify a deal worth $300 million or more? That’s certainly an interesting question that Orioles’ GM Mike Elias and the rest of the front office will have to ask themselves moving forward. 

Orioles have a few obstacles standing in the way of a Gunnar Henderson contract extension 

As we’ve seen with the Blue Jays and locking down their young franchise player, there are some substantial risks with handing out massive deals. Vladimir Guerrero Jr. signed a 14-year, $500 million contract with the Blue Jays in April 2025. While he looked solid last season, he struggled through the worst season in his career in 2026. This has been the cause of some serious concern in Toronto since Guerrero Jr. has 13 years left on his deal. 

For a better comparison surrounding a potential contract extension for Henderson, you can look at New York Mets shortstop Francisco Lindor, who signed a 10-year, $341 million deal in 2021. That may be a more realistic benchmark for Henderson to clear following his 2026 season. As the current highest-paid shortstop in baseball, Lindor earns $34.1 million a season. He’s also averaged 4.5 fWAR a season throughout his 12-year career to achieve that type of contract. 

Through his first four full seasons, Henderson has averaged 4.9 fWAR a season. But with a steady regression since his stellar 2024 campaign, perhaps Henderson would be more willing to lock down a long-term deal sooner rather than later? If not, he could risk losing even more money as his value continues to tailspin. Anything north of $35 million a year would make him the new highest-paid shortstop in the league. All things considered, that could be more than enough.  

However, Henderson is a Scott Boras client. That alone could become a major complication around the star shortstop signing an extension with the Orioles. There is already an established history with Boras clients testing the free agency market and avoiding any long-term contract extension with their current teams. It may be unlikely that Henderson would change that.  

On top of the Boras effect, Henderson has also revealed that he has dealt with a few injuries over these past two seasons. While he remained adamant that he wasn't using the injuries as an excuse for his poor performance, it's hard not to see a correlation. It's also hard not to blame the Orioles for poorly managing their young star’s health throughout the 2026 season. 

Neither of his injuries were serious enough to warrant a trip to the IL, but maybe they should have. Henderson even noted that a shoulder impingement affected his swing in 2025. He's played in at least 150 games in each of the last four seasons, but perhaps some time off would have done wonders for the shortstop? Over time, playing through an injury could exacerbate problems, potentially leading to more chronic issues. That would certainly throw a wrench into any of the Orioles' plans to sign Henderson to an extension. 

Thanks to back-to-back down seasons, Henderson is no longer a lock to receive a record-breaking contract extension from the Orioles. While he can still become one of the highest-paid players in the league, he will likely need to bounce back in a big way in 2027 to prove his worth. But with his decreased offensive production, a growing list of injury concerns, and his agent becoming a major obstacle, the possibility of a Henderson contract extension remains a complete mystery. 

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