Play ball.
That’s what, on their first opening day, Orioles owner David Rubenstein and his partners shouted to a sold-out Camden Yards.
It was a year and a half ago, and yet in the context of all that’s happened with the Orioles since — the hot start to 2024, the injuries that tanked their season, the disaster to start this one and now its uninspiring conclusion — it feels like a lifetime ago.
Because this season has been spiritually finished for months, it’s not worth waiting until everyone flies home from New York next weekend to cast our eyes forward. This is a big offseason as the Orioles look to retool and refine what remains of the roster that let them down this year in order to win again — soon.
That, we would assume, includes free agency. Rubenstein was asked about that on CBS News’ “The Takeout” podcast, and his answer, which ended up being more about last month’s pre-arbitration contract extension for Samuel Basallo, was particularly illuminating.
He said: “It’s different. The private equity world in which I’ve lived, people do well in a year, you give them a bonus and you see how they’ll do next year. But here, because of the way baseball is set up, and other sports as well, you have longer-term contracts, and we just entered into a longer-term arrangement with a young man who just turned 21, I believe it is. We gave him a long-term contract. He’s going to be here for quite some time. The price seemed high to me at the time for a person who only played four Major League Baseball games. But he did a great job. He had a walk-off home run the other night, and we’re very happy with the arrangement and we hope we can do other things like that as well.”
There’s a lot to unpack there. To me, it boils down to this: If being asked about free agency sticker shock leads you to opine about how different it feels to execute a pre-arbitration extension for a potentially elite hitter, who is far more likely to be “worth” that deal than someone a decade older than him who would get a long-term deal in free agency, are the Orioles really going to play ball on actual proven free agents?
Credit to Rubenstein and the powerful but ambiguously titled Mike Elias for signing Basallo to that contract, worth at least $67 million over eight years, with escalators and an option that can push it to $88.5 million. Similarly, credit to both for the payroll increases since last year’s transfer of control, with the Orioles moving from $92.9 million on opening day in 2024 to $164.5 million this March, according to Cot’s Baseball Contracts.
But even the most understanding critic — someone who gets why Basallo was the first top prospect to sign an extension under this regime, and why all their one-year deals last winter made sense — can acknowledge that extending a young player is among the safest ways teams spend money. Deals for veterans are far riskier propositions and take a lot more capital. They’re the kind of moves that will likely make the Orioles a contender again.

In the same podcast interview, Rubenstein shared insights on a few things, such as the joy he gets when the Orioles win. He recorded the interview the day after Jackson Holliday’s ninth-inning home run broke up a no-hit bid when the Orioles were down to their final out, sparking an unprecedented comeback win. That type of buzz is worth chasing for anyone, let alone a club owner.
So, I’m not sitting here saying that a collective as well-capitalized as Rubenstein said the Orioles’ ownership group is — with several C-suite constituents charged with making money for the franchise — is going to play the pauper this winter.
All I’m saying is his comments track with a few things we already know. When he spoke with our Andy Kostka in spring training about the team’s offseason approach, he sounded like a man who was focused more on the long-term risk associated with lengthy contracts rather than the near-term benefit. He endorsed Elias’ use of forecasts to show whether a long-term deal would be worth it, and said he was “very fond of what he has been able to build.”
This came in an offseason in which only Tyler O’Neill signed a multiyear deal, for three years and $49.5 million, albeit with an opt-out after this season. He is not exactly assuaging any fears over big long-term investments with all his time on the injured list this year. And while Ramón Laureano was a bright spot on this year’s Orioles, the lasting legacy of the free agents on short-term pacts is that, combined with millions of dollars to cover some of their salaries for the teams that acquired them, they yielded the Orioles some interesting prospects for the future.
Last year’s approach may suit everyone’s sensibilities internally, but it’s not going to have a lot of supporters outside the B&O Warehouse if they go that route again. Because of those trades, there’s more ammunition to flip prospects to bolster the 2026 roster. The Orioles have shown willingness to do that where it makes sense.
But I couldn’t help but wonder about the approach to the splashy free agents, which carry far more risk than even an unproven player like Basallo based on cost and aging curves.
Maybe we see some offers like the one the Orioles extended to Corbin Burnes, with record-shattering annual salaries over shorter terms, to minimize risk down the line. Perhaps they’re happy to pay proven performers in private equity, if the price is right and the value return works.
But the Orioles aren’t operating in a vacuum. There are other teams at play, some run by proverbial new-school executives like Elias, those who make data-informed decisions and know it’s bad business to be paying players deep into their 30s based on what they did in their 20s. Some also have incredibly wealthy owners who don’t much care about that when they have a chance to help the club now.
None in either camp would blink at the opportunity to swallow a tablespoon of risk in extending a top hitting prospect through his prime and realize incredible value if he reaches his potential. Rubenstein himself said ownership was happy with the deal, and they should be. It’s about as benign a long-term contract a baseball player can get.
Basallo’s baseball idol and bright-side player comp, Yordan Alvarez of the Houston Astros, has been worth $198.8 million, according to FanGraphs’ dollars-to-wins-above-replacement calculation, since debuting in 2019. Basallo delivering that kind of value on the contract he just signed is the kind of upside you dream of in baseball or in private equity.
I think Rubenstein and his group understand that. Where the risk isn’t necessarily skewed in their favor — the kind of deals that will make or break the Orioles’ offseason — the question remains: are they ready to play ball?
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