SARASOTA, Fla. — David Rubenstein would not be in this position, wearing an Orioles spring training quarter zip at the Ed Smith Stadium complex on Monday, if he hadn’t been a savvy investor.

The billionaire owner of the Orioles made his career in private equity. There’s a balance that occurs prior to investment decisions, and Rubenstein is well-versed in assessing the risk and reward at stake, both in the short and long term.

Those decisions can guide a business (or a baseball team) forward or leave it stalling, and Rubenstein is well aware of the interest among Baltimore’s fan base for long-term contract extensions for the team’s star players. While Rubenstein signed autographs and took photos with fans attending Monday’s workouts, one fan asked Rubenstein if he could loan the owner a few dollars to help with a deal to lock up shortstop Gunnar Henderson. Rubenstein politely smiled.

It’s not always that easy.

Rubenstein met with members of the local media for 17 minutes Monday afternoon, and afterward, he sat down with The Baltimore Banner to expand on some topics. When posed with a question about extensions from an investment standpoint, Rubenstein shed light on the internal debate for everyone involved in those decisions. When making a long-term deal, does the short-term benefit outweigh the long-term risk?

“That’s the conundrum you always face,” Rubenstein said. “If you get a pitcher who’s 30 years old, and he wants an eight-year contract, how many pitchers pitching at 38 are that good? There are some. So, that’s the issue. The way baseball operates, as you know, you get these long-term deals. If a player gets injured his first year and can’t play again, what do you do? The Nationals signed a great player, they had a great pitcher a number of years ago, and he got injured right after signing. Stephen Strasburg. And so, it’s a problem.”

That has played a role in how the Orioles go about their business under general manager Mike Elias. Rubenstein pointed out the percentage increase in payroll for Baltimore between 2024 and 2025 (56.3%) is the highest in the majors, per FanGraphs.

Baltimore signed two starting pitchers (Charlie Morton and Tomoyuki Sugano), a backup catcher (Gary Sánchez), a late-inning reliever (Andrew Kittredge) and three outfielders (Tyler O’Neill, Ramón Laureano and Dylan Carlson). The team’s payroll is up to $161 million, nearly a club record. But only O’Neill’s contract is longer than one year, and his three-year deal includes an opt-out clause after 2025 that would effectively make it a short-term pact.

And while the Orioles were in the mix for right-hander Corbin Burnes and left-hander Blake Snell, they didn’t match the high-end deals the coveted free agent starting pitchers received.

“Mike Elias knows infinitely more about baseball than I do, or [part-owner] Mike Arougheti knows,” Rubenstein said. “During the offseason, almost every day we were texting or emailing about players and opportunities and this and that. So he’s educated us a lot, and me a lot.

“He’s very, very numbers oriented, as he should be, and he has a great sabermetrics kind of team, so he doesn’t want to say, ‘Here’s a player. We can sign him for seven years. The economics show we’ll lose X dollars on it because he’s not worth it, but we’ll make somebody happy on the first day we announce it.’ And that’s not his way of doing things. He wants to make sure everything pencils out. And so, he can pencil out how many games we’re going to win a year, what the players are likely to do. It’s just amazing how he’s so accurate in these things. I’m very fond of what he’s been able to build.”

Rubenstein has largely left the team-building process to Elias, even with their constant communication. Rubenstein said he doesn’t have any financial constraints holding the on-field product back.

Behind the scenes, Rubenstein has overseen a larger overhaul. During his due diligence of the organization, he realized the business side of the franchise was “not as fully staffed as maybe we would have liked it to have been.” To flesh out that department, Rubenstein hired Catie Griggs as the president of business operations, and she has since hired several new positions in the business realm.

“What I wanted to have was more of a complete team that was as good as the people dealing with the baseball side, and Mike Elias has built a great operation, has some really talented people, and then the people on the field are really talented,” Rubenstein said. “The business side I thought needed more ballast. So we recruited some people, and Catie has really done the recruiting of those people. And I think we’re in very good shape now.”

Nearly one year ago, when Rubenstein walked around this same park on a sunny spring day as part of his assessment of the organization he had agreed to purchase, he signed autographs and took photographs with fans. But he didn’t openly advertise who he was.

He wasn’t the owner and control person yet. He didn’t meet with any players then because, as he said Monday, that would’ve been presumptuous prior to Major League Baseball approving the sale of the franchise from the Angelos family to Rubenstein’s collective.

As he walked the park again Monday, Rubenstein signed autographs and took photos with fans once again. This time he wore his now-signature Orioles hat, and he reflected proudly on the progress the club has made in a calendar year.

The questions surrounding the pros and cons of a long-term deal remain, and with free agency creeping ever closer for a young core that includes Henderson and Adley Rutschman — players with whom Rubenstein had a “social” lunch with Monday — those questions will persist.

For the moment, though, Rubenstein looks back proudly on his first year in ownership. And he’s eager for the possibilities awaiting them.

“I’m pretty happy,” Rubenstein said. “But you don’t win a world championship team in one year, or overnight. I hope we can win the World Series this year, but it’s a weird combination of things. You have to get lucky, have no health issues of consequence, have to get everybody clicking and have camaraderie in the team, and so what we’re trying to do is make the team feel we have their back. Financial issues aren’t an issue for us. We have the money to be able to do what we need to do.”