I say no on JD Drew and hope the Sox end their pursuit of him. He's just going to get hurt. Wily Mo will get on base less and play a worse right field but at least he'll play. The Sox are a better team with Manny but I know they wish to move him. It's so hard to move him right now though because there isn't a comparable bat out there to replace him with. If they wanted to go after Tejada again that would be suitable, but I can't think of much else. They would likely have to settle for a young pitcher and a good but not Manny-level hitter in exchange for him. Now if they do trade him for pitching then they will need Drew. The only good thing to acquiring a guy like Drew would be that he could play center, allowing either Wily Mo or Coco to switch to left. I think Coco would be great in left, but that would mean leaving Pena in right. Pena could be very good in left (he'd probably pick up some assists with the short throws he'd be able to make) but then the Sox would have Coco's weak arm in right. They're probably better off with him in center so long as a liability like Ramirez and Pena are out there. As for Andrew Jones, he's Wily Mo with a bit more power and great defense. The Sox need someone who will work the count and get on base, not a hacker.
I'd still like to see the Sox get Lugo. He'd be a good hitter at Fenway and could lead-off, putting either Coco or Youk in the number 2 spot where both guys could flourish (Youk may be more valuable hitting lower in the order to provide some clutch hitting once pitchers get past Ortiz and Ramirez).
As for the closer spot, who knows? Baez doesn't instill much confidence and Gagne is a question mark. If they can get Gagne and sign him to a deal that makes sense then I'm all for it but outside of those two there isn't anyone on the market. And I don't know of any closers who are available via trade. I know Scott Shields name has been thrown around. Another factor in the Manny trade scenarios is that this team no longer needs a starter (assuming Matsuzaka is signed). Shields and Wood for Manny is a no-brainer for Anaheim, and the Sox would have to try and get a little more than those two for a slugger of Manny's ability.