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Orioles’ Gunnar Henderson wants ‘winning culture’ for potential long-term deal

August 23, 2025 by The Baltimore Sun

Gunnar Henderson was one of at least a dozen Orioles players who showed up early to Camden Yards on Saturday to support the youngest among them.

Samuel Basallo, just 21 years old and less than a week into his big league career, celebrated his eight-year, $67 million contract extension with the Orioles on Saturday with a news conference. In attendance was owner David Rubenstein, general manager Mike Elias, Basallo’s family and many of his teammates, including Henderson.

The contract was the first long-term extension handed out by Elias since he was hired in November 2018. The last time the Orioles signed a core player for a contract of at least four years was Adam Jones in 2012.

Could there be more extensions on the horizon? Of course, as Rubenstein noted: “It takes two to do deals.”

Is Henderson willing to deal?

“If they bring it there, then I’ll definitely look at it with my team and be happy to look over it,” Henderson said matter-of-factly in Baltimore’s clubhouse Saturday. When asked if there have been discussions, Henderson said that he wouldn’t talk specifics about “contract stuff.”

The 24-year-old superstar shortstop said that he has one main focus when considering whether he would sign somewhere long term.

“I want to be in a winning culture. The No. 1 thing for me is being on winning teams,” Henderson said. “That’s probably one of the biggest things for me, honestly. I love winning. I hate to lose, honestly, more than I like to win. Losing is something that doesn’t sit well with me.

“I just want to be in a place where I can win, and hopefully they’ll continue to show that.”

The extension for Basallo is an example of that. Henderson said that he thought it was “only a matter of time” before the front office began extending players.

“Any time they show they value a player and then obviously taking action to show that, it is very encouraging, I feel like, for everybody here,” Henderson said.

Orioles’ Samuel Basallo savors ‘life-changing’ extension with family, teammates

After Basallo’s press conference ended, Rubenstein immediately stood up and walked to where the young core was sitting. Adley Rutschman was the first player he talked with. Rubenstein then had a lengthy and light-hearted conversation with Colton Cowser and Henderson.

Rubenstein said the Orioles’ ownership group is “fairly well capitalized” to hand out extensions. While this is the first extension Rubenstein has approved, the private equity billionaire this past offseason did sign off on significant financial commitments, resulting in a year-over-year payroll increase of 76.9%, according to Cot’s Baseball Contracts, for the largest percentage uptick for any MLB team.

“We’ve got a lot of other talented people on the team who we hope will ultimately want to spend their entire career here or spend long-term arrangements with us, and we’re committed to doing more of these as soon as we can,” said Rubenstein, who spoke with local media for the first time since spring training.

Henderson isn’t just the Orioles’ best player. He’s one of the best players in baseball. His 19.3 wins above replacement since 2023 by Baseball-Reference’s estimation ranks third in MLB, behind only superstars Aaron Judge (22.3) and Shohei Ohtani (21.0). Henderson is in the midst of a down season by his standards, and he’s still hitting .281 with an .818 OPS.

While the Orioles did take on some risk by signing Basallo so young, the total potential dollar amount of the deal is still under $100 million. An extension for Henderson, who will enter his first of three arbitration years next season, would likely cost several hundreds of millions of dollars more.

One factor that could add to the difficulty in signing Henderson, who is set to become a free agent after the 2028 season, is that he’s chosen mega-agent Scott Boras to represent him. While some Boras clients have signed extensions, most of them elect to reach free agency, which can often help a player maximize his earnings in the long run.

Boras joked during the 2023 MLB winter meetings that Elias calls “only once or twice a day” about signing Henderson (and the Orioles’ other Boras clients) to extensions. Boras also represents Jackson Holliday and Jordan Westburg.

Related Articles


  • Orioles’ Samuel Basallo savors ‘life-changing’ extension with family, teammates


  • Orioles’ Cade Povich reveals hateful message fan sent to wife on social media


  • How Orioles’ Samuel Basallo extension affects Adley Rutschman | ANALYSIS


  • Josh Tolentino: After Basallo deal, Orioles’ Elias has more bets to make | COMMENTARY


  • Samuel Basallo gives Orioles fans something to cheer about in 10-7 loss to Astros

This past winter, Boras said the Orioles were more aggressive under Rubenstein than they were under former CEO and Chairman John Angelos.

“We’ve been in very close contact with Elias, talking to him regularly. He’s made it very clear that under this ownership they’re going to take steps forward that they haven’t taken in the past,” Boras said.

Elias is often reluctant to talk publicly about extensions, but he said Saturday that he hopes there are more news conferences like Saturday’s in his future.

“These aren’t easy deals to line up,” Elias said. “We worked very hard at this, and any time we think there’s an opportunity to line up and have it make sense for both parties, it’s something we discuss and explore. … We as a front office, as an ownership group, an organization, we’re always going to continue to look to make good investments whether that’s trying to extend our own players or anything else that we do.”

Have a news tip? Contact Jacob Calvin Meyer at jameyer@baltsun.com, 410-332-6200 and x.com/JCalvinMeyer.

Filed Under: Orioles

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