As each contract extension is announced around Major League Baseball, the fervor in Baltimore rises. With the spate of extensions over the last two weeks, the feeling deepens — on the outside looking in at other fan bases celebrating a long-term deal for a franchise cornerstone.

The Orioles have plenty of those potential cornerstones. There are Gunnar Henderson, Adley Rutschman, Jordan Westburg, Colton Cowser and Jackson Holliday — and that’s only a few of the biggest names. The holdup for one of these deals between general manager Mike Elias, owner David Rubenstein and any number of players remains a mystery.

But conversations with three agents, including one of the most prominent representatives in the game, Scott Boras, show there’s no one-size-fits-all approach to these extensions. There isn’t a consensus on whether the deals young players such as San Diego Padres outfielder Jackson Merrill or Boston Red Sox infielder Kristian Campbell signed represent good value for the players.

The perspective of Boras, especially, holds weight in Baltimore. He represents three of the Orioles’ biggest stars: Henderson, Westburg and Holliday.

And while fans clamor for an extension, reality could be more difficult for two sides to match when there isn’t a rush to do so. All three players remain under team control for multiple seasons, giving Baltimore’s front office plenty of runway to sign a team-friendly deal.

“We invite clubs to offer what they choose to offer and present it to the player with analysis,” Boras said in a phone conversation. “We provide the player a complete review of all relevant contract parameters. Note that teams have control over many of these players for five or six years, so their purpose of offering a contract isn’t control. It’s cost containment. Clubs believe they can benefit substantially and save millions by signing a player in the first or second year of their major league contract.”

The idea of cost containment works for teams because it eliminates the unknown of a player’s arbitration years while sealing them for (potentially) a year or two longer than they might otherwise be under team control. A player needs six years of service time to be eligible to reach free agency; the first three years of those, players receive the league minimum, although in some cases there are pre-arbitration bonuses that raise the value of those contracts based on performance.

There are multiple trains of thought on how to approach that. A player could go year-to-year, receiving arbitration pay increases before hitting the open market. Or they could seek an extension.

In the case of Merrill, who agreed to a $135 million contract over nine years, the player preferred the stability a contract provided in an atmosphere he already felt comfortable.

“I know there’s contracts out there that are beyond absurd. There’s super amounts of money,” the 21-year-old Severna Park native said, according to The Athletic. “But having a relationship with a real human being and a real team like I have here, you can’t beat that. You can’t just sign for $700 million and want everything to be perfect. I’ve got people all around the clubhouse that are supporting me, supporting my family. They ask about my personal life every day. So, I’m just grateful for that. I know it’s gonna be the same way for the next nine years.”

Even going into the draft, Merrill was interested in the opportunity to hold discussions about potential extensions, a source with knowledge of his mindset said, and San Diego’s history of extending players made it an ideal place to land in the first round of the 2021 draft.

It’s up to the player, though, to determine that strategy.

“Most importantly, we do what our clients want,” one agent said. “I work for the player.”

And despite the outward perception that some players could have received more — Campbell, for instance, signed for $60 million over eight years — the construction of the collective bargaining agreement means teams are “playing with a stacked deck,” the agent said.

“I know no one wants to hear them [players] complain about making $760,000, because that’s a lot of money in the real world,” the agent said. “But the fact he knows he won’t get a big payday for at least three more full seasons is a real thing. That stinks. So the fact you won’t hit a big payday — and even arb one isn’t a big payday — you know you aren’t really getting paid for three more years. That’s tough. It’s set up that way. Players aren’t getting paid early enough. And especially with the adjustments in the last decade or so with teams not paying you at 35 — they’re not; 33, 34, 35, you’re getting paid less. So, if you try to do the free agency route, you’re restricted to such a narrow window.”

Still, to Boras, there may be a pattern to which players — and which representatives — agree to long-term, team-friendly deals at young ages. Front offices “look for agencies that are new or have few clients and are in need of money,” Boras said, which leaves club executives “often surprised early, well-below market contracts are accepted.”

Boras points to the lack of a full no-trade clause in many of the contracts as a downside for the player, and an indication that teams aren’t necessarily bought in for the full term of the deal.

“When you examine the majority of early deals, two common factors direct the true intent of seeking an early contract,” Boras said. “One, cost containment. And two, increasing trade value. Early deals rarely, if ever, include full no-trade clauses, meaning the club wants the right to move the player — increasing trade value — and sell off the more expensive years when the player is older.”

That doesn’t mean Boras doesn’t have players who have signed extensions. He pointed to a contract extension infielder Matt Chapman signed with the San Francisco Giants this offseason, worth $151 million over six years. Jose Altuve sealed a five-year, $125 million extension with the Houston Astros this year, too. Both players, however, are over 30, making them a different sort of extension compared to Merrill or Campbell.

When it comes to the Orioles and their inability to sign any of the Boras trio to an extension as of yet, a second agent who spoke on the condition of anonymity offered a blunter assessment: “I think it’s an easier answer than you think. I think a lot of it has to do with Westburg: Boras. Jackson: Boras. Gunnar: Boras. That’s just plain and simple.”

Boras would disagree with that assessment.

“We have executed a vast number of extensions if the player, after receiving counsel, believes they are advantageous,” Boras said.

And he said in 2023 the Orioles approached him about extensions for Holliday and Henderson.

“Those kinds of things, obviously we listen, and Mike [Elias] and I talk a lot,” Boras continued. “Obviously, our job is to filter those phone calls and relay them to the player, and kind of discuss it and see if it’s something that the player himself is interested in.”

In February, during an interview with The Baltimore Banner, Rubenstein outlined how Elias views extensions, and the outlook could be one of the major reasons a deal hasn’t gotten done.

“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?“ Rubenstein said. ”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?”

There are other avenues from which Elias could approach, too. A deal for Rutschman, Heston Kjerstad or Grayson Rodriguez may be workable. They aren’t in that 30-year-old age range Rubenstein mentioned.

But when analyzing why Baltimore hasn’t sealed one while multiple teams around the league — including those at similar financial levels, such as the Seattle Mariners — have, there are several other reasons that could be at play.

“I don’t agree with saying it only benefits the team,” the second agent said. “That’s a massive risk. You’re still talking about $100 million that you’re investing. Regardless of, again, you could be worth $1 billion, you’re still investing $100-plus million on one player. It’s still a risk.”

That doesn’t mean these agents think teams shouldn’t pursue those risks. Quite the opposite.

“I think it’s a great opportunity for some of these teams — and look at the teams that are doing it — it’s a great opportunity to kind of show off their eye for talent, right?” the first agent said. “Their ability to develop. You’ve got to make a decision, right? If you are going to do this and you miss, they’re an expensive mistake, so I applaud these teams that are going out and doing this. Of course, they’re getting somewhat team-friendly contracts. But: ‘Hey, we believe Kristian Campbell is that good, so we’re going to do this.’

“It’s probably easier for a team to not make that decision,” the first agent continued. “The battle of attrition, injuries, and over time, we’ll let it play out. But I would argue, what are your development or pro scouts or front office guys doing? Another job? Their job is to identify who’s good and who’s not, or who’s going to be good. By not exploring those [extensions], I would think the front office isn’t doing their full job, right? Maybe you’ll get judged on it. If you sign the wrong guy and he stinks, yeah, you’ll get judged on that deal. That’s true. But I imagine that’s what their job is, to identify that young talent and say, ‘We’re going to commit to you. Here’s life-changing money. Let’s go.’ ”

The Orioles have yet to sign a pitcher to a contract guaranteeing more than one year, and until signing outfielder Tyler O’Neill this winter, they hadn’t agreed to one with a position player, either. O’Neill, another Boras client, has an opt-out clause after this season, which could cut short his three-year deal in Baltimore.

As a result, there’s a perception around Elias that he likes to maintain payroll flexibility, limiting the number of heavy contracts that could prevent Baltimore from competing in the long run.

Boras said that “it’s unfair to qualify Mike or any general manager who is building up a franchise” until they have the opportunity to build toward a championship. And even then, the guidelines for doing so are set by the owner.

“Position player-wise, the Orioles are definitely in that position to add No. 1 starters to build a championship team, no doubt. Remember, ownership has to qualify what it takes to win championships,” he said.

Boras referenced Andrew Friedman, the general manager of the Los Angeles Dodgers, as an example. With the Tampa Bay Rays, Friedman didn’t pursue many long-term contracts. Nor did he with the Dodgers upon his arrival. But as the years have passed, the Dodgers became a juggernaut on the strength of those long-term deals (as well as deferred money, which isn’t a new concept).

“If you’re going to win, you’re going to have to beat the market to get top-level starters there,” Boras said. “To sign No. 1 pitchers, you’re going to have to give length of contract, because everyone in the business does, because there are only a few No. 1-type starters, and all of them have a history of getting long-term deals.”

That’s what is ahead of Elias and the Orioles. They didn’t sign one of those No. 1-type starters this offseason, which led to more vexation from fans.

The lack of extensions has, too. But the second agent said judging too harshly at this point might be imprudent. This upcoming offseason will be a larger test, the agent said, considering Cowser and Westburg will have two full seasons under their belts for front offices to judge, and Holliday will have one.

“Right now, it’s only Gunnar,” the second agent said of whom the Orioles should prioritize in extending. “You give Westburg and Cowser two years and they show consistency, then I would say, ‘OK, I should extend them, or I should at least entertain the conversation.’ And maybe they already did. I don’t know that answer. But I think sometimes teams make mistakes, and sometimes they’ve been doing their homework for a long time on the player.”