Eight questions Theo Epstein must answer in the off-season

The morning after is never pleasant, whether you are dealing with the end of a relationship or a Boston Red Sox loss in the post-season. Both situations result in the same feeling - disappointment, aggravation and, more than anything else, extreme heartbreak. Maybe I am too emotionally invested in the Red Sox, and baseball in general. As I wrote in the wee hours of the morning, an enormous pit occupied my stomach the moment Jed Lowrie's force play grounder ended Boston's season. The heartache was there when I woke up, and it will be present for awhile.

Though the sadness over last night's loss will linger, it is time to think about 2009, and what the Red Sox need to field another legitimate World Series contender. As Red Sox fans, we are resilient. We have endured disappointment before, and we will experience it again, just as we will share the exhilaration of more World Series titles. That said, right now I am going to pick myself up, dust myself off, and focus on what Theo Epstein and company should do to get this team back to the post-season next year.

In the approaching days and weeks, I will post columns and reports about Hot Stove League news. Sox and Pinstripes will be updated regularly through the off-season, so please keep the site on your list of daily stops. The first step to determining what moves the Red Sox should make is listing the questions that confront John Henry, Epstein and Terry Francona. These questions are:

1. Should the Red Sox resign Jason Varitek? Simply put, it was painful watching the captain bat this season. He did hit a clutch home run to help the Sox win Game Six, but many of his at-bats this year were similar to last night, when he struck out three times. Clearly,  his bat speed has diminished, especially from the left side, yet he is still solid defensively and manages the pitching staff effectively. I believe that Varitek should and will be resigned. A two-year deal is likely. However, the Sox MUST acquire a second catcher who can either platoon with Varitek, or at least play a couple times a week. They need their "catcher of the future." Chances are, Boston will pursue Jarrod Saltalamacchia or Taylor Teagarden of Texas. Gerald Laird, who is number one on the Rangers' depth chart, is also a possibility, as is a fourth Texas catcher, Max Ramirez. The Rangers are desperate for starting pitching, and Saltalamacchia and Teagarden are so good that it would be worth dealing Clay Buchholz or Michael Bowden.
2. Should the Sox resign Tim Wakefield? The 42-year-old knuckleballer was 10-11 with a 4.13 ERA, and he was shelled in his ALCS start, but he was also among the league leaders in quality starts, and the bullpen had seven blown saves in his appearances. Pitching depth is important, and Wakefield is ideal as a No. 5 starter. I would be surprised if the Sox did not pick up his perpetual $4 million option.
3. Should the Sox acquire another veteran starting pitcher? I think they should, and they will. Josh Beckett, Jon Lester and Daisuke Matsuzaka are one of the game's top 1-2-3 punches, and Wakefield is a palatable No. 5 option, but the Sox cannot afford to rely upon Buchholz and Bowden next season, and though Justin Masterson would be a solid starting pitcher, he has more value as a set-up man. Nick Cafardo of the Boston Globe wrote that Boston is Derek Lowe's preference. Scott Boras is Lowe's agent. The Sox will likely pursue A.J. Burnett (if he opts out of his contract with Toronto), CC Sabathia and Ben Sheets. It appears that Jake Peavy wants to stay in the National League. The cost for him in prospects would be high anyway. If the Sox would have surrendered the package Minnesota wanted for Johan Santana, they would not have reached the playoffs this year. Guys like Jed Lowrie, Jacoby Ellsbury and Masterson were instrumental in the team's success. I would rather see the Sox sign a free agent starting pitcher than acquire one via trade.
4. What should the Sox do with Julio Lugo? His trade value will be low, especially since he is recovering from a quadriceps injury. Also, he has two years left on a contract that pays him $9 million annually. Though Jed Lowrie hit just .222 from the left side, he batted .338 as a righty and provided strong defense at shortstop. Lowrie also plays a proficient third base, and can even play second. Lowrie will be the starting shortstop in 2009, which leaves Lugo in a utility role if he is not dealt. There are teams that need a shortstop. Detroit is one. The Chicago White Sox are another. There was talk a few months ago that the Sox and Tigers were considering a swap of Lugo for Dontrelle Willis. Like Lugo, Willis is signed for two more years ($10 million in 2009 and $12 million in 2010). I'm not fond of the Lugo-for-Willis idea, but I do think that Lugo will be shipped somewhere, even if the Sox have to pay part of his remaining salary.
5. What about an offensive upgrade? It's hard to admit, but David Ortiz is in decline. Injuries have taken a toll the last two seasons. The Sox are grooming Lars Anderson to eventually step in as the DH, but he will not be ready in 2009. Mike Lowell is also banged up. He had hip surgery today, and it is uncertain how healthy he will be next season. Don't be surprised if Theo Epstein trades Lowell if he can sign Mark Teixeira. Philadelphia and Minnesota both need a third baseman. The lineup would have more pop with Youkilis at third, Teixeira at first, a healthy Ortiz (if his wrist heals) at DH and Jason Bay in left field. Of course, every team with a high payroll is interested in Big Tex, who is a switch-hitter, and a good teammate and clubhouse presence. He could resign with the Angels, accept the Yankees offer or ink a deal with his hometown Baltimore Orioles.
6. Surely the Sox will not deal Coco Crisp? It seemed a foregone conclusion that Crisp would be traded last off-season. It turned out that he was a critical part of the team's success this season due to the up-and-down year of Jacoby Ellsbury and the annual injuries to J.D. Drew. Because of Drew's fragility, Crisp should remain in Boston. He will make $5.75 million next season and the Sox have a 2010 option for $8 million (and a $500,000 buyout). I think the only way Crisp will be traded is if the Sox choose to resign Mark Kotsay, who can play all three outfield positions and first base. I would like to see Boston keep Crisp and bring back Kotsay (as the backup first baseman and outfielder), but that will not likely happen since Kotsay will draw interest from teams that need a starting center fielder or right fielder.
7. Will Alex Cora return? Cora is one of the better defensive utility infielders in baseball, and he is a decent contact hitter, though he has no power and little speed on the basepaths. If Lowell was healthy, Cora would probably be resigned. However, Lowell might not be ready by next April, and the Sox will need a utility infielder with more offensive production. Juan Uribe is a possibility. He is a solid defensive infielder who can play shortstop, third base and second base, and he has some pop. Willie Bloomquist is another option. He can play the infield and the outfield, and though he does not hit for power, he does have speed. I think one or the other will replace Cora. My preference is Uribe.
8. What can Epstein do about the bullpen? Though the offense was less potent this year because of injuries to Lowell, Drew and Ortiz, and the loss of Ramirez, the bullpen was responsible for several Boston losses. Jonathan Papelbon, Masterson and Hideki Okajima form a solid core. The other four spots are open. Manny Delcarmen was inconsistent this season and had trouble finding home plate. He will likely be back, but not in a major set-up role. Javier Lopez is under contractual control of the Red Sox. The left-hander was effective against lefty batters, but he was awful against righties. I don't think a pitcher belongs in the big leagues if he cannot retire hitters from both sides of the plate, but Francona seems to like Lopez. I think he will be back. Mike Timlin will probably retire, marking the end of an impressive career as a middle reliever. If Lopez returns, that will leave two spots up for grabs in the bullpen. The Sox need another strong set-up man. Daniel Bard, a first round pick in 2006, is almost ready, but he will probably begin the 2009 season at Triple-A Pawtucket. Expect Epstein to get two relievers via trade or free agency.

With their nucleus of veterans and youngsters, the Red Sox are well-positioned to win the World Series in 2009, but the front office has some work in the off-season to fill the holes. Epstein is adept at identifying needs and satisfying them with players that fit into their respective roles. Sooner than we wanted, the Hot Stove League is upon us in Red Sox Nation, where baseball is a year-round sport. The sting of last night will be present for awhile, but it's time to shift our focus to spring training. Spark the coals of the Hot Stove!