The Orioles have an all-Boras infield. Could Alonso be first domino? | ANALYSIS

As the Orioles introduced Pete Alonso earlier this month, the slugger sat on a stage alongside the three most powerful and influential men for the future of Baltimore baseball:

David Rubenstein, Mike Elias and Scott Boras.



Rubenstein, the jovial billionaire; Elias, the shrewd executive; Boras, the punny and powerful agent.

A good working relationship between owner, general manager and Boras, the mega-agent who’s become more famous than most of the clients he represents, is important for almost every team. But it’s especially so for an Orioles team that, now with Alonso, sports an infield entirely represented by Boras.

Shortstop Gunnar Henderson, second baseman Jackson Holliday and third baseman Jordan Westburg — perhaps the three most important members of the Orioles’ young core — have all chosen Boras to represent them.

That is partially why the Alonso contract is so significant. It doesn’t just help the Orioles’ lineup, transforming it into perhaps one of MLB’s best. It doesn’t just signal Rubenstein and Elias’ willingness to spend big on a free agent.

But it shows proof of concept that those three men can get in a room and work out a deal — and it imbues optimism that the same could happen with extensions for other members of the all-Boras infield.

In one of the more noteworthy parts of Alonso’s introductory news conference, Boras named the other members of his infield — er, the Orioles’ infield — and expressed their excitement about the Alonso contract and what it could mean for the future of the ballclub.

“Having calls from Jackson and Gunnar and Westy after this was done, the light that it shines on how the players in that locker room feel about the commitment to how they can compete in really one of the toughest divisions in baseball, that comes organically,” Boras said. “The minute it’s done, it has that immediate impact, the excitement. I wish you all could hear it because it’s meaningful. It gives them a sense of pride and confidence that illustrates that this franchise is committed.

“I thank you, David, for bringing that to players, because in the player community, that’s what gives these men the confidence to go out and do what they need to do in one of the toughest divisions and play against the greats of the game.”

Henderson will be the most important player for Elias and Rubenstein to keep in Baltimore, but he’ll also be the most difficult to sign. The 24-year-old shortstop is a bona fide superstar and one of the best players in the game. Few players in MLB have provided more value to their team than Henderson has since debuting in August 2022.

Rubenstein often talks about his childhood as an Orioles fan. He brought up the 1966 World Series team and how the trade for Frank Robinson, a player he compared Alonso to, propelled that club to new heights. The 76-year-old private equity billionaire has also remarked fondly about the history of homegrown players spending their entire careers in Baltimore — from Brooks Robinson to Jim Palmer to Cal Ripken Jr.

If Henderson spends his entire career in Baltimore — a big if — he is on track to almost certainly go down as one of the best players in franchise history, perhaps earning a statue alongside the others inside Camden Yards.

But Boras is known for taking his clients to free agency, and the players who choose him as their agent know that, too. Last offseason, Boras helped garner a record $765 million contract for Juan Soto. Henderson is three years away from hitting free agency at only 27 years old, and every day closer he gets, the louder the sound of the cash register gets.

Last winter, Boras was asked whether Soto’s contract was an example of why other young stars, like Henderson, should wait for free agency rather than sign extensions early.

“I think that adage is something that yours truly has been talking about for a long time with select players,” Boras said at last year’s winter meetings. “And in situations, there’s a lot of plates that have benefited from signing early, too. They were in the right place at the right time. So, it really depends on the individual.”

At the winter meetings earlier this month, Boras was again asked about extensions for the Orioles’ young stars. Unlike Henderson, though, Westburg is one year away from hitting arbitration — MLB’s pay raise system for young players before they hit free agency — and Holliday is two years away.

While Boras players normally wait for free agency, some have signed extensions during their arbitration period, including Stephen Strasburg, Jose Altuve and Xander Bogaerts.

“That’s really something that we probably talk during the arbitration period during spring training,” Boras said earlier this month. “Mike and I have a lot of conversations on the subject, but there’s nothing immediate.”

Elias normally keeps his plans close to the vest, but that’s especially true when he’s asked about extensions. For the first six years as Baltimore’s GM, Elias did not sign a player to a long-term contract extension, making the Orioles the only MLB team not to over that timeframe. However, in August, the Orioles signed 21-year-old slugging sensation Samuel Basallo to an eight-year, $67 million extension shortly after his MLB debut.

“These aren’t easy deals to line up,” Elias said in August. “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.”

Ultimately, though, this comes down to money and how much of it Rubenstein is willing to spend. Rubenstein has repeatedly said that he and his ownership group “don’t have particular constraints” financially.

The all-Boras infield could test that in the future.

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

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