Insider Pours Cold Water on Potential Gunnar Henderson Extension

Will the Orioles opt not to sign one of their young, talented players to a long-term deal?

Mar 30, 2026; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) celebrates after hitting a home run during the first inning against the Texas Rangers at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | Daniel Kucin Jr.-Imagn Images

During the offseason, the Baltimore Orioles weren't shy about spending money in hopes of returning to the postseason in 2026.

The O's were able to sign frontline talent from the likes of Pete Alonso, Ryan Helsley and Chris Bassitt, to name a few. Baltimore also inked a long-term deal with starting pitcher Shane Baz, whom they acquired from the Tampa Bay Rays, to a five-year, $68 million deal.

The Orioles clearly sent a message under president of baseball operations Mike Elias and first-year manager Craig Albernaz that these additions, along with the other talent they have, can help them become contenders in a very competitive AL East. But with some of their other homegrown talent also seeking a payday in the coming years, this MLB Insider does not see the Orioles signing Gunnar Henderson in particular to an extension anytime soon.

Ken Rosenthal views Gunnar Henderson extension "unlikely"

Mar 26, 2026; Baltimore, Maryland, USA; Baltimore Orioles first baseman Pete Alonso (25) greets shortstop Gunnar Henderson (2) prior to the game against the Minnesota Twins at Oriole Park at Camden Yards. Mandatory Credit: Mitch Stringer-Imagn Images | Mitch Stringer-Imagn Images

During an appearance on the Foul Territory podcast, Ken Rosenthal of The Athletic called the odds of the Orioles signing Henderson to an extension "unlikely."

“The question is whether Gunnar Henderson would sign an extension below market value, because that's what these things generally are," Rosenthal said. "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.”

“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," Rosenthal added.

The odds of Gunnar Henderson signing a long-term extension with the Orioles are likely "extremely low," says @Ken_Rosenthal. pic.twitter.com/HPYG7tKO08

— Foul Territory (@FoulTerritoryTV) March 31, 2026

Henderson, as Rosenthal alluded to, is represented by Scott Boras and still has two more years of team control before he becomes an unrestricted free agent at just 26 years old. Despite coming off a somewhat down season last year, Henderson has been everything the Orioles could have hoped for when they promoted him to the big leagues towards the end of the 2022 season.

The 24-year-old was named AL Rookie of the Year in 2023, also won the Silver Slugger Award that year and was named to his first All-Star Game in 2024. Henderson also performed great for Team USA during the World Baseball Classic, going 6-for-15 at the plate with two home runs, four RBI and a 1.267 OPS.

GUNNAR HENDERSON TIES IT WITH A HOMER! #WorldBaseballClassic pic.twitter.com/aPcM4YiBVl

— World Baseball Classic (@WBCBaseball) March 16, 2026

But with the young shortstop represented by Boras and his clients generally known not to sign any long-term contract until they hit free agency, any potential contract extension for Gunnar Henderson in Baltimore may have to wait at least the next couple of years.

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