Wouldn't that be fun? Baldelli could be the DH, Crawford could play CF, with a bit of help defensively from the other outfielders and Upton could start off at 3B. I could see him moving to CF in the future if Macri can make it as a 3B, or the Twins come up with a better option there.
By the way, I think I'd go Santana, Shields, Kazmir then whomever and whomever. That would be a decent start to a rotation and the Rays wouldn't miss the players they trade for Santana with their farm system