For Epstein, the endeavor won't be quite as stressful as some other clubs, given that Boston does hold the second-best record in the Major Leagues at 55-35. To this point, only the Phillies have been better.
That said, Epstein has never been one to rest on success. The 2011 Red Sox have a legitimate chance to win it all, and the front office will work diligently over these next couple of weeks to see if there is anything it can do to increase those chances.
"We will definitely be actively involved in trade discussions, and we'll see," Epstein said. "We may be very active in trades, we may be less active, we may do some smaller things. We're certainly not a perfect club -- that's for sure. There are needs that we have, areas that we're going to attempt to upgrade. Those upgrades might come from guys we have on the 25-man roster playing better and getting locked in."
Right field is a clear dilemma for the Red Sox as the Deadline draws near. J.D. Drew's struggles have been glaring, to say the least. The left-handed hitter has a .229 average, with four homers, 21 RBIs and a .646 OPS, which is 230 points below his career mark.
The 35-year-old Drew is entering the final months of a five-year, $70 million contract. In other words, Drew could be playing for his job over the next couple of weeks.
While a trade to acquire a corner outfielder is always an option, the Red Sox have a most intriguing player already on their roster. Josh Reddick has given the team both production and energy since Carl Crawford went on the 15-day disabled list with a left hamstring strain. In 61 at-bats, Reddick is hitting .393 with two homers and 15 RBIs.
"You'd have to be blind not to notice that we're not getting much out of right field," Epstein said recently. "We're all expecting to get more out of it going forward. As I said earlier, it's a combination of letting the players with good track records play and, sooner or later, finding their stroke to produce and then also, especially while we're banged up, giving other guys opportunities and seeing who we can get hot. These things all work themselves out.
"I guess I am encouraged by the fact that we can be where we are offensively without much, if anything at all, out of right field. It will get better. There's no way we're going to have the same production the rest of the year that we've had so far. We'll improve internally and, who knows, there's a chance we'll improve at certain spots externally at some point, too. It'll get better."
The Red Sox seem to be fine offensively at all the other positions, particularly given the in-season resurgence from the catching tandem of Jarrod Saltalamacchia and Jason Varitek.
In other words, beyond right field, pitching is likely going to be where Epstein's focus is in the final weeks before the Deadline.
The rotation deserves large kudos for continuing to perform, despite a barrage of injuries. Daisuke Matsuzaka is done for the season. Clay Buchholz has been out of the mix for close to a month with back woes, and there's still no set timetable for his return. The Red Sox are hoping to get Jon Lester -- lower left lat strain -- back by July 22.
Tim Wakefield, Andrew Miller and Alfredo Aceves have all stepped in and generally kept the Red Sox in games when given the opportunity to start.
But if there's a chance to upgrade from outside the organization, Epstein will at least explore those avenues.
And, like 29 other teams in the Majors, Boston could always use another viable reliever to work in the mid to late innings. Daniel Bard and Jonathan Papelbon are a nice 1-2 punch at the back end, but it's still hard for the Sox to know quite what to expect from Bobby Jenks. Since Rich Hill went down for the season following Tommy John surgery, the Red Sox have lacked a shutdown lefty.
With so many teams still in contention, Epstein could face an even bigger challenge than normal to add from outside the organization.
"I can't sit here and say we're definitely going to go out and make a blockbuster trade," Epstein said. "For one thing, there's just not a huge market of sellers right now."