Who are you thinking here? I'm guessing Tork might not yet be one of them. 😁
Henderson is a Boras client, so that's a no, at least on team-friendly terms. FWIW, so is Jackson Holliday. Plus, Holliday is the #1 prospect on the Orioles, and #1's probably don't do that.
The time to lock up young talent to long team friendly contracts is before they start raking in the bigs, that is, before they know they can succeed so they are motivated to lock in the security. Once they start succeeding in the majors, once they know they're good enough to get good and paid, that team-friendly window is shut. Rutschman is already a 2x All-Star now so no incentive for him to sign on team terms. Kjerstad is killing it right now, so he also might be too far gone for that. Maybe Cowser, who's struggling right now so you can buy low, plus he topped out at #4 on Pipeline, like Colt Keith. So, sign him to that contract.