If the Sox trade Betts because they are convinced that there is little to no likelihood of his staying here once he hits free agency, I can accept that as a rational approach. There is no rule that says that Betts automatically goes to the Sox if they are the largest bidder; he could very well decide that there are a handful of places he would prefer to Boston for whatever. We really don't know; he hasn't said anything publicly, other than that he wants to test the free agent market. If Boston were to be one of five bidders, it could mean that Boston has a 20% of keeping Betts. That is something that has to factor into the thinking of the Sox front office.
At the very least, the baseball operations department would not be doing their job if they weren't at least calling other teams to see what the trade market for Betts looks like. And, if the trade is handled correctly, there is still a chance the Sox could be a suitor for Betts' services next offseason.
However, if, OTOH, the team feels the need to trade Betts (or let him walk next year) simply because of financial constraints imposed upon them by existing contracts and artificial tax ceilings, I would be frustrated. That is not how good organizations are run. I can even accept that there is a limit to what they should pay Betts and for how long (even if I cannot articulate that limit). I just have difficulty accepting that the team could not afford to pay him the $30-35M AAV that is being discussed just so they can pay Eovaldi $17M. If that's the reason, Henry deserves as much blame as Dombrowski, if not more. The Sox front office somehow managed to pawn off the Ramirez and Sandoval decisions onto Cherington. As they say, fool me once, shame on you; fool me twice, shame on me.