But what I keep coming back to when I try and think of a feasible deal
@YTF is that one of the issues with that approach is, of course, generally that type of deal requires some manner of high level pitching prospect going back to the other team, and we quite simply don't have that.
Obviously we're not getting Pedro - but that required Pavano whom was a very highly rated prospect at the time (I think he might have been the highest rated SP prospect in the game). Schilling of course didn't require that, but he clearly wasn't young or cost controlled. Beckett required Sanchez (#40 on BA before the 2006 season) and Sale needed Kopech in there (top 100 on BA and BP, MLB at 16 was obviously the outlier). Heck, even Drew Pomeranz required Espinoza (who was somewhere between top 50 and top 25, depending on if one wants to go with his pre 2016 or pre 2017 ranking as a 2016 deadline deal).
It's really why I think Boston has kind of painted themselves into a situation where the realistic choices are a) spending big on the FA market or b) having another season of craptastic starting pitching. They don't have a good rotation to start with. They haven't spent on "controllable" even mid rotation arms in the past 5 years and they have - at least relative to the rest of the prospect industry - nothing for pitching in the minors (sure there are guys who might be good, but for whatever its worth the prospect ranking complex doesn't think much of them).
They'd probably have to over-spend in terms of prospects to get a decent pitcher because they don't have pitching to give back - or find a team that is so awash in pitching but lacking in hitting as to find a deal. Which is why I keep going back to Seattle and Miami as teams I'd target. Because it's going to be tough to deal with anyone else because both the MLB pitching and (at least for a "top farm system") the minor league pitching is terrible.
Maybe the move isn't to search for a young cost controlled starter, but an established name under a large contract. A name I keep thinking about is Alcantara from the Marlins. He's coming off easily his worst season since he became a full time member of the rotation. He's still "cheap" but with the Marlins being the Marlins, it's a large salary for them, and his salary jumps from $6m last year to $9.3m this year, then $17m and $17m. BTV has his value as "only" around 15.3 right now (less than Kutter Crawford, for instance - which I think is laughable) but with all their pitching would they consider moving him for hitting. That's a call I'd hope Breslow is making.
Edit - yes I know he induces a lot of ground balls, yes I know the Red Sox IF defense is garbage. But the only two teams I can even realistically think of where they might trade pitching for hitting are the Mariners and the Marlins, nobody else really has that luxury. Possibly Cleveland.