The Orioles made shortstop Gunnar Henderson an extension offer during last year’s Spring Training that wasn’t accepted, the New York Post’s Jon Heyman writes. It isn’t known if the two sides have revisited talks this year, though Heyman feels the chances of an agreement are a “long shot” at best. Henderson is represented by Scott Boras, whose clients usually eschew extensions in favor of eventually testing free agency.
Henderson is in his first year of arbitration eligibility and is set to become a free agent after the 2028 season at age 27. Between that relatively young age and the numbers he has already posted in his four big league seasons, Henderson and Boras may well have a record contract in mind for the shortstop’s entry into the open market, which could leave the Orioles priced out.
This isn’t to say that the O’s haven’t shown an increased willingness to spend since David Rubenstein bought the team in early 2024. Baltimore’s eight-year, $67MM deal with Samuel Basallo last August marked the team’s first long-term extension in over a decade, as the Orioles hasn’t yet locked up any of the other young talents amassed during their rebuilding period. This offseason, the O’s made a big splash in free agency by signing Pete Alonso (a Boras Corporation client, no less) to a five-year, $155MM deal that stands as the second-largest contract in franchise history.
It isn’t out of the question to suggest that it would take three times’ Alonso’s contract to extend or re-sign Henderson, given Boras’ penchant for pushing the market. Henderson would have to keep playing like a superstar, of course, and the 2025 season was a slight bump in the road since he hit a relatively modest .274/.349/.438 over 651 plate appearances, with 17 homers and 30 steals (in 35 attempts).
The shortstop still posted this 120 wRC+/4.8 fWAR production, however, while dealing first with an intercostal strain that sidelined him during Spring Training, and then a shoulder impingement that bothered him for most of the regular season. Returning to normal health should help Henderson regain his power in 2026, and perhaps he is gearing up for a season more akin to the 37 homers and .281/.364/.529 slash line he delivered in 2024.
Perhaps the Orioles want to see Henderson back at full strength before considering more extension talks, in order to determine if he is worth the kind of landmark investment it would take to keep him in the fold. Alonso and Basallo are the only long-term commitments on the Orioles’ books, so a mega-deal for Henderson perhaps isn’t out of the question if the O’s view him as their franchise cornerstone. As Heyman noted, however, the likelier scenario is that an extension isn’t reached. This would mean Henderson either walks in free agency, or Baltimore could conceivably look to trade him (maybe during the 2027-28 offseason) in order to gain a larger return.
