But now, with the Dec. 8 start of the Winter Meetings at the Bellagio hotel in Las Vegas imminent, expect Epstein to start sinking his teeth into some impact moves.
Despite the glitzy setting of this year's Meetings, Epstein won't be one to mingle in the lobby and make small talk.
If past Winter Meetings are any indication, he will stick to the bunker of his suite and contemplate his options.
Perhaps the most glamorous among them is free-agent first baseman Mark Teixeira. Although the price tag figures to be enormous -- perhaps as high as $20 million annually -- what is not to like about Teixeira?
He is 28 years old, not to mention a powerful switch-hitter who gets on base and plays excellent defense.
It's for that reason that Epstein will have plenty of competition if he decides to go all-out for a man who hit .308 with 33 homers and 121 RBIs last season.
The Red Sox have Kevin Youkilis at first base, Mike Lowell at third and David Ortiz at designated hitter. However, five years ago, Epstein had Nomar Garciaparra -- then a superstar -- at shortstop and that didn't stop him from nearly acquiring Alex Rodriguez in a trade with the Texas Rangers.
When it comes to the Winter Meetings, Epstein doesn't always pull off the blockbuster move, but he is almost always thinking about one. Such was the case last year, when he feverishly pursued Johan Santana, who ultimately was traded from the Twins to the Mets.
One thing that helps Epstein immensely is that he is bargaining from a position of strength. Without making a single move, the Red Sox already have options at every position heading into 2009. And, without another move, they would probably be considered one of the favorites to win the 2009 World Series.
"We have the ability now to be selective in free agency," Epstein said recently. "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."
Because Manny Ramirez and his $20 million salary are off the books, the Red Sox have some financial flexibility.
If it isn't used on Teixeira, the Red Sox could sign a starting pitcher. CC Sabathia, the most expensive of this year's free-agent pitchers, doesn't appear to be on Boston's wish list.
But the Red Sox have had discussions with agent Darek Braunecker about ultra-talented righty A.J. Burnett. Those talks could pick up in Las Vegas, where Burnett figures to get plenty of interest after winning 18 games and striking out 231 for the Blue Jays in 2008.
Then there is Derek Lowe. The sinkerballer was a fixture for the Red Sox from 1998-2004, playing the role of postseason hero in his final few games with the club. After four years with the Dodgers, Lowe, who has perhaps the best track record of durability of any starting pitcher in the game, is again on the market.
Lowe has already stated his interest in coming back to Boston, but the Red Sox have yet to divulge how mutual those feelings are. At the very least, Epstein will probably keep tabs on Lowe through agent Scott Boras.
In fact, Epstein will likely spend plenty of time with Boras, considering the power agent also represents Teixeira and catcher Jason Varitek.
Varitek has been a fixture for the Red Sox since becoming the team's primary catcher in 1999, but now he's on the market.
Complicating the situation is Varitek's age -- he'll be 37 in April 2009 -- and the fact that he's coming off the worst offensive season of his career.
Perhaps the Red Sox could find common ground with Varitek if the team's captain since 2005 agrees to a somewhat reduced role where he could help mentor a young catcher Epstein might be able to find somewhere on the market this winter.
"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."
Varitek, according to Boras, would not be high on playing less.
"Jason wants to catch every day; he wants to play every day," Boras said. "He has a lot more left in his career."
As in any Winter Meetings, Epstein and his staff will examine a number of different areas of the club.
Though Ortiz recently suggested adding another 30-homer hitter to the lineup, some players don't think the Red Sox need a lot of tinkering after winning the World Series in 2007 and going all the way to Game 7 of the American League Championship Series in '08.
"My advice to Theo and them is to have a good offseason and have fun," said Youkilis on Nov. 18. "Some guys on this team have said, 'We need this; we need that.' We've got a great team. We'll be good."
Epstein will continue to explore ways to make the Sox an even better team.