There are a few obvious areas to work on. Others would be nice to upgrade. In no particular order...
1. Get Adrian Gonzalez. I was pushing this back at the trade deadline and I am far from the only one pushing it today. The Boston Globe ran a whole article about how important that kind of move would be for the Sox yesterday. He is a young, affordable left-handed power hitting first baseman who would make the Monster his personal playground. The only downside is that former Assistant GM Jed Hoyer is now the GM in San Diego and he knows not only how much Boston covets Gonzalez but what the players in the Boston system are worth. But San Diego is going nowhere fast and even though he is the face of their franchise, San Diego has to know that Gonzalez is their only asset that could be traded to start rebuilding the franchise.
If the trade went through, you'd have Gonzalez at first and Youk at third. Then it's a question of who do you keep at DH, Lowell or Ortiz? Tough call; Ortiz had the better power numbers but Lowell had the better average, OPS and has a very tough contract to move ($12M in 2010). But I think it is clear one of them would have to move on.
2. Re-sign Jason Bay. The more I look at the Jeremy Hermida deal (a great move in and of itself) the more this nervous voice in my head says "Theo is going to run with Hermida is Bay doesn't sign the Sox offer. NO!" That, I think it is clear, would be a huge mistake. A outfield platoon on the bench of Hermida and Baldelli would make my day. But left field must be occupied by Bay for the Sox to compete in 2010, and that means the Sox have to pony up the dough.
36 homers, 119 RBI, a .921 OPS and a clean fielding sheet make Bay's case with crystal clarity. He is the best option the Sox have in left (don't even pretend Holliday or Jermaine Dye is an equivalent choice) and the Sox will regret it for years to come if they let Bay walk. This is THE most important move for the Sox in the off-season.
3. Figure out what the hell they are doing at shortstop. Since letting Cabrera walk after the 2004 season, shortstop has been the bleeding ulcer on the Red Sox body. The only guy who has stepped up in the intervening five years and stabilized the position is Alex Gonzalez...and the Sox just turned down his option. Now, I understand why they did that ($6M is a bit pricey) but the Sox are taking a risk. Both sides say they will negotiate, but free agency is free agency and anything can happen. If he should walk, the Sox are left with an injury-prone Jed Lowrie as the primary shortstop. Not a good place to be come February.
4. Find one more starter. The Sox need, I feel, one more solid starter to push their rotation over the top. And this will be interesting to watch. Usually, getting a top-level starter is only possible through trade. If the Sox do pursue Adrian Gonzalez, then a lot of their best chips won't be on the table any more. But this year, there is a prime target in John Lackey. And the Yankees, having signed CC and AJ last year and exhibiting a new awareness of what players cost, probably won't be in the hunt.
Lackey will be 31 and coming off of seven 10+ win seasons in a row. He would be a nice compliment to Beckett, Lester and Buchholz in the rotation. And while he costs more money, he doesn't cost you any prospects.
The other two options that leap to mind are Feliz Hernandez in Seattle and Roy Halladay. If the Sox trade for Gonzalez, then forget about King Felix. The prospects required for either deal make pulling both off near-impossible. But Halladay...it might be possible. He isn't happy in Toronto, Riccardi completely botched the trade deadline last year and his value to the Jays deteriorates every day he remains on the club. The Jays have limited talent and some serious cash issues. In short, it's a ideal situation for the Sox. While dealing for Halladay would cost Buchholz at a minimum, he would give the Sox a front three that rivals any other team.
5. Who catches? This is something that will get more press in the days and weeks ahead. The Sox like V-Mart as a catcher/1B hybrid because it gives them so much flexibility in their lineup. But Youk and Gonzalez at the corners obviates the need for a regular rest period since Lowell wouldn't be there. So that means to keep Martinez's bat in the lineup would require him catching on a regular basis. And so how does that dovetail with Varitek, who will likely return at that $3M option he holds for 2010? I suppose you could use V-Mart as your DH, but then you're catching Varitek almost all the time and either Lowell or Ortiz is rotting on the bench. This is a lesser issue since it depends on something else occurring first, but it could become a major issue in a hurry.