Offseason starts with these five

Compared to most other clubs, the Red Sox have relatively little to worry about as they enter the offseason. They have one of the highest payrolls in baseball. They have a productive farm system. And they are coming off a season in which they fell one win short of another trip to the World Series.

No matter how you slice it, things really are not that bad.

In fact, they're quite good.

Nonetheless, the Red Sox just lost to a team that spent roughly $100 million less on its player payroll in 2008, something that cannot go overlooked. For all the Red Sox have accomplished in recent years, there are a number of places where they have spent their money unwisely. Shortstop and right field most quickly come to mind, particularly when Julio Lugo now looks like a $9 million bench player and that J.D. Drew has given the Red Sox roughly the same production (at $14 million a year) that Jayson Werth has given the Philadelphia Phillies (at an average of roughly $1.3 million).

That's not Drew's fault.

That's gross overspending.

With all of that in mind, here are five of the biggest questions facing the Sox this winter:

5. Is Jacoby Ellsbury front and center?
By all accounts, Ellsbury is still the center fielder and leadoff man of the future. At the same time, it's a bad sign when your starter essentially does not play in the final five games of the league championship series. A year ago at this time, many assumed the Red Sox would deal away Coco Crisp. As it turned out, Crisp saved their bacon by outplaying Ellsbury over the final two months.

Big props for Coco there. A lot of guys would have sulked, quit and lamented their plight by that stage of the season.

Thanks to Crisp's play, the Red Sox have some strength from which to deal here. Crisp's value currently may be higher than at any other point in his Sox career and Ellsbury still has great promise. (The inconsistencies in his game are most likely a product of inexperience.) It could be that the Sox view Crisp as nothing more than a fourth outfielder, but they may be able to get something of value for him particularly if it addresses one of the next four questions.

Survey question: What should the Red Sox do about Coco Crisp?

4. What to do with Justin Masterson?
Before anyone suggests that the Red Sox need to improve their pitching staff, slow down. Assuming Josh Beckett's health, the Sox are in good shape here and have better targets than Jake Peavy on which to spend their resources. Remember, too, that the Epstein and his staff have excelled at producing pitching, in particular, and that the Sox still have Clay Buchholz, Michael Bowden and Daniel Bard, among others.

All of this brings us back to Masterson, who is a pivotal player here. If the Sox anticipate him being a starter, they may need some bullpen help and Buchholz becomes a bargaining chip. If Masterson is a seen as a reliever, the Sox may need to keep Buchholz and Bowden for depth in 2009. In either case, the Sox need to establish some sort of plan for Masterson, at least as it pertains to the short term.

Survey question: What should Justin Masterson's role be next season?

3. Is Jed Lowrie the answer at shortstop?
Defensively, we know the right answer here as Lowrie outplayed Julio Lugo by miles. Lowrie batted .193 in his last 34 games of the regular season but general manager Theo Epstein said the rookie shortstop played with a small nondisplaced fracture in his left wrist since May, an injury that got worse as the season wore on.

At one point this season, the Sox actually wanted Lowrie to get some work at first base, too, but they didn't want to burden him with too much. Regardless, the Sox need to decide where Lowrie fits in and just how much money they would be willing to eat to part ways with Lugo (two years, $18 million remaining). At the moment, Lowrie looks like he would make a great utility player; of course, we once said the same thing about Dustin Pedroia.

Survey question: Is Jed Lowrie the long-term answer at shortstop for the Red Sox?

2. Should the Red Sox re-sign Jason Varitek?
On Monday at Fenway Park, Epstein gave a nice view into his philosophy of building a team. Said the GM: "If we do our jobs well, we should be at least league-average at every position. We can pick our spots where we can be above-average, even elite."

For a long time, thanks largely to Varitek, the Red Sox were elite at the catcher position. Now … not so much. During the regular season, Red Sox catchers ranked 13th among the 14 American League teams in OPS, 13th in slugging, 10th in on-base percentage, last in batting average, 12th in RBIs, 13th in total bases and last in runs scored. We all know what Varitek, who will be a free agent this offseason, means to the club behind the plate, but the Sox can't afford an automatic out in the lineup, either.

The point: Either Varitek needs help, particularly from the left side of the plate, or the Red Sox have to do something even more drastic.

Survey question: Should the Red Sox re-sign Jason Varitek?

1. Does the lineup need a heart transplant?
A year ago at roughly this time, the Sox began the World Series with David Ortiz, Manny Ramirez and Mike Lowell batting in the Nos. 3-4-5 positions; this year, they were effectively without all three. Lowell was injured, Ramirez was in Los Angeles and Ortiz was ailing or ineffective -- or both.

In the end, the Red Sox offense was not nearly as imposing.

The good news is that Jason Bay arrived and Kevin Youkilis emerged, which seems to give the club a good starting point. From here, the Sox need to decide whether they want to keep Bay here beyond 2009 (and if he wants to stay), and if both Ortiz and Lowell can return to the form of 2007. Again, the Sox already have had internal discussion about pursuing free-agent-to-be Mark Teixeira, for whom the competition will be fierce.

If the Red Sox prove serious about acquiring Teixeira -- and if they succeed -- they need to deal Youkilis, Ortiz or Lowell, the last of whom seems most likely given the combination of his skill set and age. If they fail to acquire Teixeira, the Sox may have to upgrade at another position, which brings an enormous number of trade possibilities (Matt Holliday? Garrett Atkins?) into the equation.

Survey question: Should the Red Sox sign free agent first baseman Mark Teixeira this winter?

(Editor's note: Check out the gallery version of this feature.)