Look, if paying down some of Hamels' contract gets you a package of Betts, Bogaerts, Bradley, and Owens for example, I'm all for it. I want the talent, and the Phillies can afford to eat some salary. But I think you're either overstating how much money is owed to Hamels or understating how good he is. You can't just compare it to what has happened recently, either. The market isn't the same as it was when those other deals happened, and the need may just be greater for Boston right now since they've really gone all in this offseason. They NEED some starting pitching badly, and I don't see Shields alone being an answer.
If we were talking about sending him to Oakland or Tampa, where efficiency matters much more, I could understand it. But Boston not only can afford to pay for it, they're probably getting more bang for their buck than they are paying anyway. It's a really fair deal. For a team like Boston, this contract looks more like a positive than a negative, honestly. I don't want to ignore the contract: I want to celebrate it. They are locked in to a top-15 pitcher for five years where his value will likely not diminish much over the course of the deal and they're not overpaying so they're not hamstringing themselves.
It really is a fascinating debate, and I appreciate that you're arguing the merits of it. You have a very reasoned argument and a lot of good points. It's refreshing to read a debate about the Phillies' transactions without it devolving into "LOL Amaro overvaluing his players again." Because this is one of the few times in the last five years where I feel like Amaro is playing this right.