This deal is (surprisingly) not going to include Chase Headley.
The Sox have a need, but not a whole hell of a lot of money to spend. That need is starting pitching. The Padres don't have a lot of money, and they're blowing their team up so that they can start again in the future. That is why they should trade their starting pitcher Tim Stauffer to Boston for SS Jose Iglesias, and OF Alex Hassan.
Why the Sox should do this: Tim Stauffer is nothing special. He put up exactly one win above replacement level last year. He's got a 75% LOB, a .282 BABIP, a 3.71 xFIP. Stauffer is average, average, average. He gets just over 50% ground balls, and his FB% hangs around 30. But the cool thing about Stauffer is that because he is so decidedly average, he made about $1 million last year, and in his second arbitration hearing he'll probably make something like $1.5 million. Bringing in such an average pitcher on such a low salary means that we have money to spend elsewhere. He's a hole filler for nothing money and nothing prospects. Iglesias is never going to hit above AAA in the Boston system, he's not even hitting at AAA now, his glove plays better in Petco because they care more about run prevention than run scoring. Hassan is a nice-ish piece, but does anybody see him leapfrogging Kalish, Sweeny, and Lin? We send those two to San Deigo, and open up a 40 man roster spot. We also spend negligible money, add a solid #5 starter, and have some cash to make a run at Oswalt, Kuroda, or Maholm.
Why the Padres should do this: The Padres have more time to let Iglesias figure out if he can hit the ball, both Jason Bartlett and Orlando Hudson are signed through 2012 with options for 2013. If Iglesias shows signs of picking up, they potentially have Omar Vizquel ready to replace Bartlett in 2013. Alex Hassan exactly fits the Petco Park offensive profile, he gets on base a whole hell of a lot, but power really isn't part of his game. Low OBP, high power players don't make a whole lot of sense in Petco, but Hassan's .400+ OBP does. Hassan is a decent player who could become part of an intriguing outfield with Cameron Maybin in the coming years. The last reason the Padres should do this is that they aren't looking to contend in the two years that Stauffer has left with them, and if they can get these two pieces in Hassan and Iglesias, it would be worth the loss of a decidedly average pitcher.