I think this deal would be a great move for the Yankees. If you dealt Hughes, you could move Joba into the 8th inning and once again have a bridge to Mo Rivera (so much for the Bruney plan). This would free up a spot in the rotation where you could plug in Halladay. Imagine what the Yankees pitching would look like: You have two Cy Young winners in Roy Halladay and CC Sabathia. Then you have the nastiest pitcher in the majors in A.J. Burnett. If Wang can return to his former self than you have the best 4th in the majors (if not, you could move a Zach McCallister into the rotation in his place and deal him for prospects). And Andy Pettitte can still pitch as evidence by his team-leading 8 wins.
The bullpen would also benefit with that move. By putting Joba back in, you end teams hopes when losing after seven. Plus, if Bruney can regain his form you can end the game after the 6th inning. Imagine how many wins that would save for pitchers that get taken out early.
Now losing a guy like Romine (they should definitely deal him over Jesus) would be a blow to the organization, but it wouldn't leave them empty-handed as they already have an abundance of catchers in Montero, Cervelli, and newly-drafted J.R. Murphy.
I don't know who the Blue Jays would ask as a third prospect, but I'm guessing it wouldn't be Jesus Montero or Zach McCallister. Maybe they'll take a lower down guy such as Melky Mesa. Or maybe they'll pick a guy to fill a hole like Ramiro Pena or Ed Nunez (they're losing Marco Scutaro soon).
The last scenario is probably the one the Yankees hope for: what if the Blue Jays wanted Chien-Ming Wang? Then the Yanks could deal him, Romine, and I'd say Melky Mesa. Then they could keep Hughes in the bullpen or switch him with Joba. We'll see how the Yankees play this one.
But no matter what they do, they really should try to get the Doc.
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