Austin Konenski
The Baltimore Orioles, led by Pete Alonso and Gunnar Henderson, are on the rise going into the 2026 MLB season. Baltimore made several key additions over the course of the offseason, including Alonso, Taylor Ward, and Shane Baz. However, will the Orioles be able to extend Henderson beyond the 2028 MLB season?
Baltimore offered a long-term contract to Henderson last spring; however, the odds of an extension are a “long shot” at best, as reported by the New York Post’s Jon Heyman. The Orioles star shortstop is represented by agent Scott Boras, who typically takes players to MLB free agency to maximize their contracts.
Henderson is in his first year of arbitration eligibility and will become an unrestricted free agent after the 2028 MLB season at 27 years old. Based on Henderson’s age and production, a record-breaking contract in MLB free agency is a possibility. This could leave the Orioles out of the mix to sign Henderson.
In 2025, Henderson had 17 home runs and 68 runs batted in with a .787 on base percentage. It was a regression from Henderson’s 8.8 WAR campaign in 2024, but the Orioles weren’t as productive in 2025. Despite the drop in numbers, the 24-year-old star should be among the favorite for AL MVP in 2026.
It is unclear if the Orioles have approached Henderson with an extension since last spring; however, a player of his caliber typically reaches free agency. Other Boras clients, such as Juan Soto and Bryce Harper, were rewarded with major contracts exceeding $300 million.
If Henderson continues to be a franchise cornerstone in Baltimore, he could be rewarded with a record-breaking contract. The Orioles will have more opportunities to extend Henderson, but the odds aren’t in their favor.
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