While Epstein will have a number of issues on his plate as it pertains to the 2009 team, the one hot-button topic surrounds the uncertain status of Jason Varitek, the team's invaluable catcher and captain.
Coming off what was easily his worst season offensively (.220 average, 13 homers, 43 RBIs), Varitek, who will turn 37 in the first month of next season, is a free agent.
But despite the reality of his birth certificate and his struggles offensively, Varitek was still a key asset for the Red Sox in 2008, providing immeasurable leadership for the pitching staff and serving as a rock-like presence behind the plate.
In the near future, Epstein will sit down with Scott Boras, Varitek's agent, and see if the sides can find common ground.
"He's an important part of the organization -- there's no doubt about that," Epstein said. "Obviously he's coming off a year that wasn't his best, but he's important, nonetheless. Now, he's a free agent and we'll be talking to him. We have an obligation to explore all our options. We do that with every position."
It's a little different, however, behind the plate, where there isn't a ton of depth throughout the industry.
"There's not a lot of elite catching out there," Epstein said. "But at the same time, that changes the standards for what you're looking for. What we like to do is be league average at every position, and then be way above league average at as many positions as we can. We try to have no weak links and be at least league average at every position. It's well-documented that there's not a lot of elite catching out there, but we'll figure it out."
As far as the players are concerned, they hope that Epstein's solution is to go with the status quo and bring back Varitek, who wasn't at Fenway Park during Monday's media access period.
"If I walk into Spring Training and don't see Jason Varitek, it will be a day that will be very eye-opening and very sad," said Red Sox first baseman Kevin Youkilis. "He's a guy that I've come to know and come to play next to all the time. I've spent five seasons around him. To not have him there will be a tough thing for me personally and for a lot of guys in this room."
Varitek chose not to discuss his future late Sunday night after the 3-1 loss to the Rays in Game 7 of the American League Championship Series. But the fact that he had tears when a reporter asked if it could have been his last game with the Red Sox demonstrates the emotional ties Varitek has to the team and the city, which he's been a part of since 1997.
Clearly, Epstein is keeping all options open.
"Jason's an important guy here, and we'll sit down and explore if there's a way for him to come back that will help be a positive solution for our catching situation," Epstein said. "If there is, I'm sure he'll end up coming back. If there are obstacles we can't overcome, sometimes that's beyond our control. It's an important one. He brings a lot to the table here despite not having one of his most productive years. We'll sit down and talk about it."
Catcher is the position the Red Sox are most unsettled at as it pertains to next season. Here is a look how other areas of the club shape up for 2009:
Starting pitching: The Red Sox probably have more options at this spot heading into the winter than any other team. The big three of Josh Beckett, Jon Lester and Daisuke Matsuzaka will all be back. The Red Sox can bring back Tim Wakefield, the veteran knuckleballer, at a mere $4 million option, which is a bargain for a pitcher who is good for double-digit wins virtually every season. The 42-year-old Wakefield has left no hints about being ready to retire. Young Clay Buchholz, who got rocked in multiple stints in the rotation, is currently gaining his confidence back in the Arizona Fall League.
And the Sox also have the option of moving Justin Masterson back to the rotation, though the sinkerballer might be too valuable in the bullpen at this stage of his career.
Even with all the security, don't be surprised if Epstein makes a play for Jake Peavy, or any other elite starters that go on the trade or free-agent market.
"You look at our starting pitching. We can bring back our starting core and make minor tweaks, and I think we can be strong with that," Epstein said. "That said, is there an opportunity potentially to improve our starting pitching? Absolutely. We'll probably spend a great deal of our time this winter trying to figure out how to improve."
Veteran Curt Schilling, who didn't pitch at all in 2008 because of right shoulder and bicep woes, is a free agent. He's likely to retire. Schilling said he might consider pitching for half a season for somebody, but the Red Sox don't seem to be a fit. Paul Byrd, the finesse righty who helped stabilize the rotation after his arrival in August, is also a free agent and unlikely to be back.
Bullpen: Again, the Red Sox are in good shape here. Dominant closer Jonathan Papelbon is eligible for arbitration, but he will be back. The 1-2 setup punch of Hideki Okajima and Masterson will also be back. However, if Masterson gets moved to the rotation, Epstein will look for another key righty. Manny Delcarmen, who might have the best pure stuff of all of Boston's relievers, will be another returnee. The Red Sox also have contractual control over lefty specialist Javier Lopez, who had an underrated season.
"If we brought back our bullpen, would we have a pretty good bullpen? Yeah, I think it'd be pretty darn good, as evidenced by the way they pitched after coming together the second half of the season and into the playoffs," said Epstein. "That said, will we look to improve the bullpen? Absolutely, we're going to spend countless hours trying to improve the 'pen."
Mike Timlin, the 42-year-old righty who has been with the Red Sox since 2003, is a free agent and likely to announce his retirement in the near future.
Infield: Three of the four starters are set. Youkilis, who filled in admirably at third base during the postseason, can go back to first base. The Red Sox expect a full recovery from third baseman Mike Lowell, who underwent right hip surgery on Monday. The team hopes that Dustin Pedroia, its little sparkplug, will be the second baseman for years to come.
The question mark is shortstop. Julio Lugo became a forgotten man after tearing his left quad just before the All-Star break and not playing for the rest of the season. Switch-hitter Jed Lowrie, yet another solid find from the farm system, played steady defense and had some pop at the plate, particularly right-handed. But he struggled to get hits late in the season and into October, though his walk-off single to clinch the Division Series will be a lasting memory from this postseason.
"I think we have some depth and some options, which is not a bad place to be," Epstein said. "We'll monitor Julio's recovery. There's no reason to believe he'll be any way affected by the injury. He was going to potentially be available for the World Series had we won [Sunday] night. I think he's got a lot to offer. I think he's also got a lot to prove. I think he and Lowrie can also complement each other very well. We'll see what the offseason brings, what direction is best for the organization or if it's best to let it play out on the field."
Outfield: Jason Bay, who fit in seamlessly after being acquired for Manny Ramirez, will again patrol left field. J.D. Drew, hopefully over his back woes, is the right fielder. The question is whether the Red Sox will again rotate between Jacoby Ellsbury and Coco Crisp in center, or if one of those players will be dealt this winter.
Because of injuries to other areas of the outfield, both players wound up getting plenty of playing time. They also finished the opposite of the way they did a year ago. This time, it was a surging Crisp supplanting the slumping Ellsbury in the middle of the ALCS.
"We feel we're really bullish of the future of both of those players -- Jacoby and Coco," said Epstein. "Coco's year was a testament to his perseverance. Look at where he was and where he ended up. I think a lot of people in this room and a lot of people a lot of places would be surprised how far he came and how much he contributed in the end, given the situation he found himself in at the start of the season. There's no reason he can't do it again next year. And Jacoby is a good young player who is going to get better every single year."
Center field is definitely a position of strength for the Red Sox, which means it could be used as a chip to strengthen another area of the team.
DH/bench: David Ortiz, the big slugger, will benefit from a winter of rest so he can get his left wrist back up to par. After suffering a partial tear of his tendon sheath and missing seven weeks, Ortiz was never fully able to get back to 100 percent. But Epstein said there's no reason Ortiz can't be back to relentlessly mashing opponents next season.
As for the bench, Kevin Cash should again be part of the catching equation, assuming Wakefield's option is picked up. Alex Cora has been an important contributor in the infield since coming over from the Indians in July 2005, but he's a free agent. Cora enjoys playing in Boston. His status could be affected by whether Lugo is traded. Sean Casey lived up to his reputation as one of the friendliest people in the game, and did a solid job off the bench during the first half. But his role became diminished after Mark Kotsay was acquired in August. Casey and Kotsay are both free agents.
Epstein said that Kotsay will probably first pursue opportunities to play every day somewhere else. The 34-year-old Casey said he'll spend time with his family before deciding what is next in his career path.
The big picture: The Red Sox had an unusually quiet winter last year, as Casey was one of just a precious few new faces in Spring Training. Expect Epstein to make more changes this winter. It's just a matter of what they are.
"We have the ability now to be selective in free agency," Epstein said. "That could be the case, but we could also do something big. We have the ability to survey the field, play the offseason game and do what we think is right without having to do any one thing."
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.