I don’t think it’s a matter of seeing more of him. I think it’s a matter of mitigating risk in terms of years. I think 6 years is the absolute maximum, and a 3-5 year extension is more likely. (I’m assuming 2025 is already taken care of, so everything starts in 2026.)
I don’t see how what he would earn in free agency is relevant; the entire point is to pay him less and Crochet’s goal is to get earlier security. And as Crochet has openly stated he wants an extension, I would guess these free agent prices won’t ever come up beyond this thread. The Sox aren’t desperate here because of what they traded to get him; it was fair compensation for 2 years of an elite talent. Crochet likely isn’t desperate either, but again, has expressed willingness, which could mean he knows he won’t be getting paid like a free agent.
I think they get him extended before opening day, and it will be in the 3-5 year range. Money is tough to determine; I don’t know what Crochet will settle for. But I would throw out a range in the $22-25mill AAV, presumably with the AAV going down as the years went up. I am not going to speculate on team options, but they are more likely than opt outs, because it’s the Sox looking for protection whereas Crochet should be looking for security. If the Sox added one or two very high AAV team options, it might make sense for both sides. I’m talking $26-30mill AAV team option(s).