Question: Gunnar Henderson, Jordan Westburg and Jackson Holliday are all represented by Scott Boras, who has said that he wants his young, talented clients to go into free agency. How will the Orioles deal with the potentially very large salaries in 2026, 2027? It seems to me that they will have to offer these three players very large contract extensions to mitigate Boras’ modus operandi. From: Carl LaVerghetta Annapolis
Answer: That would be a happy problem to have, Carl. Other than outfielder Tyler O’Neill, who’s also a Boras client and has an opt-out after the 2025 season, the Orioles don’t have any players signed to contracts beyond this season. Relief pitcher Andrew Kittredge, whose contract is not yet official, reportedly has a $9 million option for 2026.
While the team’s payroll is currently $155.8 million, much of that money is allocated to players who will be free agents after 2025, so there’s great flexibility to sign multiple young players to extensions.
Question: At arbitration hearings, does a team attorney criticize a player in front of them? Is the player there, either physically or via video? From: Timothy Morris, Butchers Hill
Answer: Tim, always good to get questions from Butchers Hill, a great neighborhood. The press doesn’t cover arbitration hearings, but from my understanding, teams try not to make the cases personal, although it’s understandable that players feel that way.
It’s my understanding that it’s more of presenting cases of comparable players rather than focusing on if a player has, for example, a poor average with runners in scoring position.
Jorge Mateo is the only Oriole slated for an arbitration case this year. He’s asked for $4 million, and the Orioles have offered $3.1 million. His agent will try to make the case why he’s worth $4 million by finding examples of players similar to him, and the team will do the same. The players are present for the hearings.
Most weekdays, I’ll be answering at least one Orioles question. If you’d like to submit a question, send it to: Rich@BaltimoreBaseball.com. Questions may be edited for clarity, length and style.