If Boston strikes out in free agency, I'd be open to something like this I think.
Bosh, Winslow
for
Amir, Jerebko
I wouldn't want to keep Amir and Jerebko in that situation anyway, so just send them to Miami so they don't have as much a trade exception.
I think that Bosh is worth that kind of flyer, though it is obviously a huge risk, and you would have to have all of the medicals and feel like there is a good chance Bosh is going to play at some point.