Orioles have the blueprint for their young stars after Pete Crow-Armstrong extension

Last season, the Baltimore Orioles extended their top prospect, Samuel Basallo to a deal that could potentially keep him on the team for the next nine seasons for less than $100 million. It's a deal that benefits both sides, but especially the Orioles. If Baltimore could get all of their top prospects to sign the same type of contract, they would.

Unfortunately, the Orioles weren't able to convince any of their other young young players to follow in Basallo's footsteps. Most of them have either played well enough during their short careers that they'd turn their nose up at an eight-figure contract or haven't played enough to prove themselves one way or another.

Orioles should follow the Cubs example with Pete Crow-Armstong

The extension that the Chicago Cubs gave their young star centerfielder, Pete Crow-Armstrong, could serve as a blueprint for what some of the Orioles young stars might actually be willing to sign if the Orioles would offer it to them.

The extension Crow-Armstrong signed is for six years, $115 million. The deal is backloaded, but that's an average annual value of $19 million. For the Cubs to get a 6.0 WAR player to sign a deal that pays him an average of $19 million for his age 25-30 seasons is great value. Why would Crow-Armstrong do this?  

The answer is because he had four more years under team control. This deal pays Crow-Armstrong $55 million over those four years. That's more than he was going to make just going through the arbitration process, especially the first couple of years. So he gets a significant pay raise over the next four years. After that, the last two years of the deal, which would have been free agent years, pay Crow-Armstrong $30 million each.

The Cubs get what they want: two additional years of Crow-Armstrong's prime at a number that's reasonable. Crow-Armstrong gets something he wants: a pay raise for the next four years and fair market pay for the two free-agent years he's giving up.

Part of what makes the Crow-Armstrong extension work is where he is in his career. He debuted in 2023. In 2024, he played a good chunk of the season and was valuable on defense, but poor on offense. Then he broke out in 2025 and got paid.

There aren't any Orioles in that exact situation, but if any one of Coby Mayo, Colton Cowser, Jackson Holliday, or Dylan Beavers had an all-star caliber season, they would be in a similar position to where Crow-Armstrong was this offseason: Just a few years into their careers with one great season under their belt.

Holliday is another Boras client, so he is unlikely to accept any extensions. However, if any of the other players mentioned had a great 2026 season, a Crow-Armstrong style extension where the player gets a pay raise through arbitration in exchange for two to three additional years of control at a fair price would make sense if the Orioles were willing to put that kind of money on the table.