No doubt everyone is closely following the quest for Johan Santana, the Holy Grail of lefthanded pitching. The prevailing wisdom is that the trade market for the Twins has been narrowed down to three teams; the Dodgers, Yankees, and Red Sox. The Dodgers seem to be a distant third however, so it's basically Yanks versus Sox, again.
Before I get into who might be changing hands, let's look at the dynamics for a minute.
Santana becomes an FA after next year, and it's already been made clear that the Twins cannot afford him. They could try to keep him and take a flyer on running the table next year with he and Liriano as a solid one-two punch, but it's unlikely. If that doesn't fly and they try to deal him mid-season but this would lessen the return for him. So there is some incentive to deal him now, for sure.
The Twins, however, do not utterly control the terms of this deal. Santana is the best pitcher to come available in a long, long time, but there are the dual constraints of his ongoing cost, and the fact that Bedard, Haren, and Willis are hanging out there as well. Moreover, it is still a case of teams betting against each other. The Twins can demand player X all they want, but if the price is too steep, it's too steep. Both teams know they (the Twins) are not going let themselves end up with just the compensatory draft picks, and this mutual ceiling is to the benefit of the Sox.
The ceiling I'm referring to is the "untouchables". For the Sox, it's probably Buchholz and Ellsbury, and for the Yanks it's Joba and Hughes. The benefit to the Sox is that if that ceiling stays the same for both teams, the Sox proposed package of Lester, Crisp, Lowrie and Masterson/Bowden wins. And let me tell you, if that package brings back Santana (and there is no reason it shouldn't, working in a vacuum; Bill Smith is getting a lot of major-league ready talent there), we should just rejoice, plain and simple.
If it doesn't, because NYY dealt Hughes (Joba I think probably is untouchable), then it sticks in the craw, but it's not a total disaster. The package would likely be Hughes, Cabrera, Jackson and Tabata or Hughes, Jackson and Cano. That would mean that they dealt two or three of their top prospects/young players to get Santana, and that helps the Sox out to some degree in the long run.
The reason it's not a total disaster is because the Sox will have kept Ellsbury, arguably the most exciting homegrown position player to put on a Sox uniform since Yaz, and Buchholz, a pitcher who is simply a mind-boggling talent.
If the Sox have to give up Ellsbury, and Santana stays healthy for the duration of his contract (this aspect has been largely ignored in all the discussion I've read - Santana has a lot of wear and tear on the arm and stumbled badly in the last couple months of 2007), it's a palatable trade. However, if they give up Buchholz, I don't like the deal. Buchholz is pretty well past the prospect stage now, and has every indication of being the next Santana himself - Keith Law recently stated that right now CBuck has the best change-up in baseball. It should be noted that this pitch is how Santana makes his money, working off a fastball that he commands better than Buchholz does his, but with a curveball that is far inferior to CBuck's.
Giving up the talent currently on the table, possibly with Ellsbury over Crisp in the deal, plus paying the $20-25M per year to extend Santana, makes some sense, because a rotation with Beckett, Santana, Buchholz, and DiceK in it for the next 5 years is simply insane. But when you factor in that you are trading what is likely to be equivalent talent in the one arm (Buchholz), plus three other players, plus the cost/risk of the extension - then the Sox are getting screwed. I say hell no. Hell no.