Seriously. And not because Boras is a BAD agent. he's a great agent, if what you want is, as jacksonian said, guaranteed money. If you want to get on a team or find a place that suits you well its a crap-shoot. Boras was Varitek's agent and his contract seemed a little overpriced at 10m a year, but I wasn't too disappointed with it.
I think there will be one very telling interaction. Matsuzaka, his translator, Theo, LL, perhaps TW and a select group of the other sox brass will sit down. Matsuzaka will listen to them, listen to them talk about baseball and their hopes for the team and for Matsuzaka and their description of Sox nation, and Matsuzaka will either think "THIS is what I want. THIS is what baseball is all about" or he will think "I don't feel comfortable with this." It is essentially a mutual interview. Schilling walked away from thanksgiving and his time on SOSH saying "Damn, these guys know their stuff. They approach baseball the way it is supposed to be approached." Let's hope its the same with DM.