Willingham might at first appear to be a good buy-low candidate, since his hitting, while still decent, is down a bit from his last two seasons. (He has a 110 OPS+ in 2011, compared to 127 in 2009 and 129 in 2010.) He’s also right-handed and has hit lefties well in his career, which would make him a good match for a Pirates team that has lefties Garrett Jones and Alex Presley to handle open positions at first base and corner outfield, but little in the way of right-handed talent at those positions. (They’ve got Jose Tabata, of course, but I’m taking for granted that he’s a full-time starter.)
The only problem is that Willingham typically only plays one position, left field, and he’s really bad at it, canceling out some of his offensive value. Also, PNC Park’s left field is enormous, and the Bucs would really be giving up a lot by sticking a lead glove like Willingham out there.