The main reason this all will not work is that the only teams that will take on Ray and KG are teams that feel that they are the missing piece for a title run. So what we would be left with is bad contracts and late 1st round picks. That is the harsh reality of this debate. Anyone who thinks otherwise that we will magically get a mid 1st or a lottery pick for KG or Ray is delusional themselves. Boston fans in general have been obsessed for the last few years with the notion of rebuilding and building a dynasty in sports, which doesn't happen overnight but you have to do this the right way. Why not simply let the contracts expire? Hell that's the argument everyone seems to make with the Perkins trade, that we would have been better off letting him just go and pulling off a sign and trade.
Why hamstring the cap for the next 3-4 years for the price of late 1st round picks that you can just buy from a team anyways? That's essentially how Boston got Rondo...they kicked in x amount of cash and some scrubs. Portland was notorious for selling their late first rounders for 2 or 3 years. This has happened before, there are other ways to get 1st round picks that won't screw the cap.