In a savvy move last season, the Baltimore Orioles locked in their top prospect, Samuel Basallo, with a deal that could keep him in Baltimore for the next nine years for under $100 million. This contract is a win-win but tilts in favor of the Orioles.
If they could replicate this kind of agreement with all their top prospects, they certainly would. However, convincing others to follow Basallo’s lead has been a challenge.
Many young players have either proven their worth beyond an eight-figure deal or haven't yet shown enough to warrant such a commitment.
The Orioles might want to take a page from the Chicago Cubs' playbook with Pete Crow-Armstrong. The Cubs secured their rising star centerfielder with a six-year, $115 million extension.
This deal is structured to pay Crow-Armstrong an average of $19 million annually, which is a smart investment for a player delivering a 6.0 WAR. Why did Crow-Armstrong agree to this?
He still had four years under team control, and this contract gives him $55 million over those years-far more than he would have earned through arbitration, especially in the early years. The final two years, which would have been his free-agent seasons, net him $30 million each.
For the Cubs, it's a strategic win: they gain two extra years of Crow-Armstrong’s prime at a reasonable rate. For Crow-Armstrong, it’s a financial win: a significant pay increase now and fair market value later.
What makes Crow-Armstrong’s deal particularly effective is his career timing. After debuting in 2023, he had a mixed 2024 season-strong defensively, but lacking offensively. Then came his breakout in 2025, earning him this lucrative contract.
While the Orioles don’t have anyone in the exact same situation, players like Coby Mayo, Colton Cowser, Jackson Holliday, or Dylan Beavers could find themselves in similar positions if they deliver an all-star level season. Holliday, however, being a client of Scott Boras, might be a tough sell on extensions. Yet, if any of the others shine in 2026, a Crow-Armstrong-style deal-offering a pay bump through arbitration in exchange for a few more years of team control-could be a wise move for the Orioles, provided they’re ready to invest.