Personally, I don't see this trade working out. Giles has Boston on his list of teams he can't be traded to, IIRC. And while Boston is willing to pick up the remainder of his contract, San Diego will still want some talented prospects for Giles, and I'm not sure Boston will be willing to pick up the entire contract AND give up talented prospects as well. The reason I don't see it working out is because Boston already has a pretty dense outfield, which cuts into Giles' playing time. Bay in left, Drew in right and Ellsbury and Crisp in CF. I'm not sure how keen Giles would be to DH, either, and Boston already has Ortiz at DH. It is interesting that Giles hasn't made it public that he's blocking the trade at this point, so maybe he would like a chance at a World Series ring. But, you still have to get Padres management to sign off on lesser talent for basically their second best player.