Insider reveals why Orioles will face 'difficulties' re-signing Gunnar Henderson

One MLB insider got very honest about the Orioles' expected attempts to re-sign star shortstop Gunnar Henderson.

Aug 13, 2025; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) looks on during the first inning against the Seattle Mariners at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | Daniel Kucin Jr.-Imagn Images

Comments that Baltimore Orioles star shortstop Gunnar Henderson made earlier this week when asked if he’d consider signing a contract extension with the Orioles in the future turned heads among the baseball community.

“If they bring it there, then I’ll definitely look at it with my team and be happy to look over it," Henderson responded, per an August 23 X post from Jacob Calvin Meyer of The Baltimore Sun.

When Henderson was asked what matters most to him when considering whether to sign somewhere long-term, he added, “I want to be in a winning culture. That’s the No. 1 thing for me... Losing doesn’t sit well with me. I want to be in a place where I can win, and hopefully [the Orioles will] continue to show that.”

Henderson (who will be entering his first year of salary arbitration eligibility this offseason) didn't seem overly enthusiastic about wanting to re-sign with the Orioles, to say the least. While he didn't reject the prospect of re-upping with Baltimore outright, reading between the lines makes it pretty clear where his mind is at in this regard.

Aug 21, 2025; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) looks toward the crowd after an at bat during the seventh inning against the Houston Astros at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

MLB Insider Sends Clear Message About Gunnar Henderson, Orioles Contract Negotiations

In hindsight, Henderson's lukewarm attitude toward an Orioles contract extension should have been expected, given who he's represented by. This is the stance that The Athletic's MLB insider Ken Rosenthal shared during his August 24 appearance on Foul Territory.

"Certainly, [the Orioles] are willing to spend money. We've seen that. We saw that last offseason, and we saw that with the Basallo extension," Rosenthal said. "So it was encouraging to see the Orioles finally get [a contract extension] done. Mike Elias has not given out an extension to a young player in his tenure before the Basallo deal.

"[At] the same time, you're gonna have difficulties with Gunnar Henderson and Jackson Holliday. Both are represented by Scott Boras. Both are more inclined, perhaps, to go to free agency than other players would, because Scott prefers his guys to establish their values on the open market," Rosenthal added.

"Doesn't always happen that way. But generally speaking, that is what Boras clients do."

It's no secret that Boras' clients are typically pushed toward free agency rather than re-signing with their respective teams, as this is a scenario that plays out with multiple elite players every winter.

Therefore, the Orioles will likely not only have to jump this hurdle when trying to lock Henderson down, but they'll also need to overcome it when trying to secure Jackson Holliday.