Absolutely. If it will take 200 mill to resign Headley, that would be silly. The guy has a .770 career OPS. The problem is that Middlebrooks is going to take some time to figure it out in the majors, and if the Red Sox continue playing like they do, he's the weak link.
The challenge at the trade deadline is that the Red Sox have many good players, but few great ones. Being able to upgrade the team significantly over mid-tier players like a Gomes or a Morales will be costly. In terms of upgrading the team for a championship run without sacrificing talent, I can think of no other way.