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.
“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”
It’s always weird when an article says this and then quotes a deal like Basallo’s as if it’s some big number. That’s peanuts compared to what Henderson and Boras will be asking for so the comparison is so weird to make.
It’s not weird at all for the O’a. Badallo’s deal qualifies as the fifth largest total dollar deal in franchise history. Alonso’s is second. Whatever they offered Henderson would be the biggest one yet. All under the helm of Rubenstein.
I probably wouldn’t take it either. Gunnar will eventually break the bank.
Assuming he stays healthy. Nothing is a given these days. It’s a gamble. Seager, Tulowitzki, Correa, and so on. A lot of superstar SSs can come out of their early years and look like a future HOFer, but then something goes awry and it never quite pans out exactly how they thought.
Not saying that’s what’s going to happen here, but nothing is a given in baseball. Esp. health.
I stopped reading after I saw Boras’s name.
I’d could see him signing with Yankees, Dodgers or Red Sox if he makes it to free agency. If O’s can’t extend him, they should trade him 1.5 years before he hits free agency.
Mets and Blue Jays will likely be in the mix.
Love Gunnar and want him to be in Baltimorefor life. But he’s not worth 450m to the orioles Sorry
yes he is. that’s the cost of doing business.
Another future Yankee returning to terrorize the Os like Mussina
This genuinely makes me so sad. I really hope the Os just hand Henderson a blank check. Should’ve done it with Machado, and now they have a second chance of sorts. Watching another ultra talented infielder leave might break O’s fans.
I’ve accepted what is inevitable. We have 2 more years before deciding whether we need to deal him or make another run with him.
As an O’s fan, in order to see the team remain competitive and be perennial contenders, we will need to get used to the idea that, for whatever the reasons, if the team is unable to extend premium talent, they will likely get dealt in order to bring higher upside talent back into the organization – at least that would be the prudent business decision in order to continue to keep pace in the division and ensure a strong steady cycle of talent keeps rotating throughout the club. While it would be wonderful to see some of our guys extended and retained, the business of baseball proves that sometimes such a situation isn’t possible.
I thought he was done after 2027. He won ROY and gained a year of eligibility
He was up the full year already. Didn’t impact anything.
Clutch – He did gain a year of eligibility when he won ROY … but he would have either way.
They could always further extend Mountcastle before his value drops.
Perfect timing for that little nugget. I needed some levity.
Just extended him already, geezz. Blank check, and official adoption papers to be Rubenstein’s favorite son!!
The Chris Davis contract probably still makes the Orioles somewhat nervous even though it is a new administration
Gunnar is a stud. If they can find a way to pay him they should
I doubt that has been considered at all otherwise they wouldn’t have signed Alonso, who is closer to Chris Davis’s profile than Gunnar is.
Last spring, as in…2025? Must be a slow news cycle now that all OD rosters are set.
As a side effect, Gunnar’s projected contracts numbers make Witt Jrs extension look like a huge bargain. If you assume Gunnar gets around $40m in the two arb years, he’ll be a FA when Witt is still locked in for 2 more years and Gunnar will only be about $15m short in earnings. He’ll blow past Witt with the new contract before Witt has his first opt out (which, absent injury, Witt will exercise).
The market has inflated that fast.
Witt left $ on the table which is the norm with early career extensions. Gunnar has priced himself out of Baltimore I believe.
Well, if he didn’t accept last winter, surely the amount that would have been offered this winter would be lower based on 2025. He wouldn’t be accepting this year.
He’s going to want to bounce back up to that 150 OPS+ land or so, to increase his future extension value.
Supposedly he was playing hurt much of last year so with that and Alonso and Ward protecting him in the lineup 30+ HR and other # improvements should be expected.