All right gang, here's my hot take before bed. I don't think the Sox screwed this up at any stage. They got Xander's pre-arb years, and they signed him to a nice extension and got three more years with him. Then he opted out and got bonkers money for his thirties. It's not clear any extension a year or so ago would have enticed him to not opt out, at least not any extension that wasn't also bonkers.
There's a tendency around here to give the front office too much agency, like they can do whatever they want if only they try hard enough. But the team can't control players, or control other teams, and they just have to make the best choices with the hands they are dealt. I think they did that here. So long Xander, thanks for everything, interested to see what's next for this team.