Hello there, OTM. My potential trade is:

Red Sox trade Youkilis, Ranaudo, Bogaerts, Doubront, and Bryce Brentz to Blue Jays for Jose Bautista and Henderson Alvarez.

Red Sox do this because:

They need a right fielder, Bautista is one, and why would they not want Jose Bautista? He was clearly the best hitter in baseball last year and would give them a big right handed bat to even out the lineup. He can also play 3rd, with questionable skill, but the point is he is physically capable of helping fill the hole Youkilis would leave. The Sox also need cheap starting pitching, so really any deal they do right now should also involve getting a starting pitcher. Alvarez has shown good control and gotten good results for most of his career and is ready to jump in to a big league rotation. The prospects in this deal would be a huge price to pay, and I'm not saying it would be a great move. I tried to dig into the farm system while still leaving it with depth, balance and skill. But if the Sox could get the current best hitter in baseball for a package centered around Youkilis they would have to do it. Remember, we're talking about the BEST HITTER IN BASEBALL. Like Albert Pujols good. Bautista would utterly transform even the game's best offense into something so much greater.

Blue Jays do this because:

They have an unbelievable trade chip in Bautista. Why not sell high on him as he enters his 30's? They get a guy in Youkilis who will actually replace a lot of his offense for the next year or two, as well as multiple top prospects. And giving up Alvarez is a lot easier when they get Doubront, a major league ready pitcher, and Ranaudo, the top starting pitcher in the Sox' system.

Or should we give up even more and go for Romero?