Two minutes before the biggest player press conference in this town in years, Orioles players swarmed the seats in front of the dais that suddenly felt packed.
Adley Rutschman. Colton Cowser, Jackson Holliday. Jordan Westburg. In the second row, Gunnar Henderson sandwiched himself between me and Banner reporter Andy Kostka, slurping on a slushie.
It was a reassuring show of support for their teammate Samuel Basallo, who just became the Orioles’ $67 million man by signing a contract extension just five days after his big league debut.
But what they got from Baltimore’s leading owner was a challenge: Which one of you is next?
There was a lot to like about Saturday’s celebratory press conference with Basallo, who at 21 represents a lot of things to a lot of stakeholders. On the diamond, he’s one of the game’s hardest-swinging young prospects. In the organization, he’s this front office’s first million-dollar international signing who has paid out by reaching the MLB and the poster child of the team’s Dominican Academy efforts.
Most important, Basallo’s deal is proof that the Orioles ownership group — which took over in March 2024 led by David Rubenstein — is willing to take a big swing on a young player like every other MLB club, a longtime deficiency of the John Angelos era.
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On Saturday, Rubenstein, wearing an orange-striped tie, made sure he was on the dais next to Mike Elias, a lately embattled general manager who clearly has his support, and there was no second-guessing his directness.
He wants to see more of these deals.
“The Orioles’ ownership group is fairly well capitalized, and we have the resources to do these kinds of deals,” he said. “It takes two to do deals, but we thought this was a perfect one for the first one of this type.”
There was a bit of surreality to hearing Rubenstein relay that message — we’ve got money, we just need to open the dialogue — with Henderson sitting directly to my right.
If there is any other Oriole who needs to be locked down for the long term, it’s Henderson. The 2023 Rookie of the Year, No. 4 in the 2024 MVP ballot and homegrown prospect would represent even more to the franchise if it could secure him past 2028, when he can enter free agency.
Henderson was understandably unwilling to talk about the topic at length in the clubhouse, but he told reporters his strongest consideration is being with a winning organization. He said would examine any offer by the Orioles. “I will definitely look at it with my team and be happy to look over it.”

That is complicated by his agent, Scott Boras, who famously advises clients to enter free agency in the hopes of cashing in on mega deals in their primes. Juan Soto’s record-setting $765 million deal was engineered in no small part by Boras, who undoubtedly would like to see Henderson sign for half a billion or more in a few more years with a franchise that can afford it.
In a way, Boras is responsible for Saturday’s festivities in Baltimore. In the 2021 offseason, the Yankees were expected to sign Basallo, then a promising Dominican teenager. But, when New York shelled out $324 million for Gerrit Cole, it reduced its international bonus pool — and allowed the Orioles to pounce with $1.3 million, the team’s largest international signing bonus ever.
All of this predates this ownership group, however, and since then Boras’ clients have been a sore subject. Henderson, Westburg and Holliday are represented by Boras. Boras client Corbin Burnes spurned an offer to stay in Baltimore last offseason and later complained that the proposal didn’t have enough years (the evidence suggests he wanted to go to Arizona all along, but whatever).
It should be noted, too, that Rubenstein probably unintentionally struck a nerve in January when he said he favored a salary cap for MLB — a position that could come back to haunt him as players and owners entrench themselves to renegotiate their collective bargaining agreement after the 2026 season.
For Rubenstein and his pals, who have boasted of their robust resources, they’ve struggled to find one of their young players willing to take their money.
“These aren’t easy deals to line up,” Elias said.
Well, hold your horses for a second.
Elias said he and Basallo’s agent, Gio Rodriguez, began talks Sunday when Basallo debuted. In less than a week, the two sides had agreed to terms. Maybe they can be easy.
There is always uncertainty on who should take the blame when a deal doesn’t get done — but now that the Orioles have done one, it’s clearer that at least some of the onus on the failure to extend the team’s young core falls on the core itself. It’s not that these players are wrong to play the long game and listen to their agents, but with the signing of Basallo, a fan base that wants to see long-term extensions may gradually shift its frustration from ownership to the players.
Citing Jim Palmer (who celebrated a jersey giveaway Saturday night), Brooks Robinson and Cal Ripken Jr. (who is in the ownership group himself), Rubenstein highlighted the legacy of career-long Orioles — echoing a well-known desire of fans.
“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,” he said. “And we’re committed to doing more of these as soon as we can.”
It was hard to gauge the reactions in the room, especially with the rows right behind me that undoubtedly were chewing on those words — “as soon as we can.” With Basallo’s deal, Rubenstein and Elias delivered a message to the young core that they’re here to talk.
“This group has put us in a position where a lot of these things are much more possible and that we have the ability to make an investment like this,” Elias said. “To build new facilities across the minor leagues and in Sarasota, to raising the payroll like we did over the winter to continue to explore these type of contracts, either with our own homegrown players or with free agents, this is all on the table thanks to this group.”
The Orioles gathering for Basallo’s press conference were bargaining for a celebratory atmosphere. What they got was an inflection point.
The team owner said in no uncertain terms that Baltimore wants to have more days like this one — and a good number of players in that room could be next, if they’re willing to say yes.
The hope is, at the next extension press conference, Henderson is at the dais and not just in the gallery.
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