After making a splash by signing shortstop Marco Scutaro, Epstein heads to Indianapolis, where the Winter Meetings will take place from Dec. 7-10.
"It will be typical," Epstein said recently. "Some stuff will happen at the Winter Meetings, and things will fall into place after that."
After solving the shortstop situation by signing Marco Scutaro last week, the Red Sox need to figure out if Jason Bay is coming back or if another left fielder -- Matt Holliday? -- will need to be signed or acquired to take the slugger's place.
Unlike the past two winters, when Boston's lineup and pitching was fairly well set and additions seemed more of a luxury than a necessity, Epstein has some vital moves to execute over the next few weeks.
But aside from filling the obvious holes on the roster, perhaps the most fascinating thing that will take place at the Meetings is how engaged Epstein gets with other teams in regard to a blockbuster trade.
The Blue Jays have made it no secret that Roy Halladay is available. And now that the big righty has made it clear he has no intentions of signing with Toronto long term, there's a likelihood that he will be moved, perhaps even by the end of the Meetings.
Sure, the Red Sox have a formidable rotation of Jon Lester, Josh Beckett, Clay Buchholz, Daisuke Matsuzaka and Tim Wakefield. But Epstein never shies away from going after elite players. The question is this: How much would Boston be willing to trade for the 32-year-old Halladay, who will command a long-term contract in addition to top-of-the-line talent.
The financial investment would not be as hard for the Red Sox to stomach as being forced to package Buchholz with another top young arm such as Daniel Bard or Casey Kelly.
Two winters ago, the Red Sox went to a certain point in talks for the Twins for Johan Santana, and then walked away when the price -- Lester and Jacoby Ellsbury -- was too high for their liking. Expect Epstein to go in with a similar strategy this time around.
It could be that Epstein spends more of his time talking with former assistant Jed Hoyer, the current Padres' general manager, about a trade for Adrian Gonzalez. The left-handed-hitting first baseman has a swing that seems made for Fenway Park. At 27 years old, he is just now entering the prime of his career.
"Everybody always will welcome a 30-home run hitter," said Sox slugger David Ortiz. "At any time, any day, any situation. To compete with [the Yankees], you better bring it, period. We always need help. We always need guys capable to produce. Not only us, everybody. That's why everybody is chasing guys in the offseason who can provide power, RBIs, you know. This is a team that's playing in the [American League] East. Everything is powerful right here."
For nearly a year, Boston has had conversations with agent Joe Urbon about a long-term deal for Bay. It stands to reason that the Red Sox and Bay -- now a free agent -- should know by the end of the Meetings if their relationship will continue.
Meanwhile, in addition to their interest in bringing Bay back, the Red Sox have also been gauging the market for Holliday, a comparable free agent who plays the same position. Holliday is represented by Scott Boras, the power agent Epstein has had several major dealings with -- some which have ended well and others that haven't -- in his time as general manager.
Will the Red Sox make major moves this winter?
"I think it could go a number of different directions. I think we're always open to change, because I think you need change to improve as part of the natural cycle in baseball and in life," Epstein said earlier in the offseason. "Sometimes the market doesn't bear that out. Sometimes there aren't the right fits, sometimes it's not the right free-agent market and sometimes you end up with more status quo than you want.
"If that's the case, if we look back three or four months from now and say, 'Wow, there weren't major changes,' then I think next year will be perhaps the last year of this main group of players. We have a lot of players going into contract years next year -- I think it might be one more chance with this group to go out and win the whole thing."
Then again, with Epstein involved, don't rule out some major changes. Bold moves have never scared him in the past.
"If we are able to make changes, maybe that transition we talked about will happen earlier than some people expected. I think it could go one of both ways," Epstein said. "I think we have a nice set of about 10 pre-prime or prime players that we're going to build around and eventually we'll get more. Whether that happens this winter or in subsequent winters or when that group of really talented 18-20 year olds is ready, that remains to be seen. We're open to all possibilities. We'll see how it develops."