The confidence comes from the faith he has in his staff, who are working to make the 2008 amateur selection process another successful re-stocking of an already bountiful farm system.
"It's a good feeling sitting in the draft room, knowing we have a sound player development system," Epstein said. "And for me, it's a great feeling as a GM, looking around the draft room and seeing our scouts. We've had a lot of continuity in this department the last few years. I think four or five years ago, we were trying new things and trying to get all on the same page as to what we're looking for, and now we know
The Red Sox certainly found what they were looking for in 2005.
In what has generally regarded as the richest and most productive Draft in recent Red Sox memory, the team selected, in order, Jacoby Ellsbury, Craig Hansen, Clay Buchholz, Jed Lowrie and Michael Bowden with their first five picks in 2005.
"I think what makes a good Draft is hitting on players in the first few rounds," Epstein said. "If you look back on our most successful Drafts, they've been the ones on which we've hit at the top of the Draft. Take 2005 for example, which we point to a lot of times in the room as sort of the idea model of what we're shooting for."
The top four players have already made significant contributions at the Major League level, with Bowden drawing closer with every pitch. The right-hander was perfect through six innings on Tuesday night for Double-A Portland in an 8-1 Sea Dogs win over Erie.
"It looks like we may have hit on the first five players in that Draft," Epstein said. "You'd love to do that every year. If that's where the most talent is available, that's where you don't want to make mistakes."
And mistakes aren't likely when you have a talented group of scouts understanding the mission of the organization.
"Now we just go out, all on the same page and we know what we're looking for, it's just a matter of finding it," Epstein said. "I think the fact that we have a lot of confidence in our player development department allows us to shoot a little bit higher in the Draft in terms of impact.
"When I first became GM, we were focused, as we started to refine both our scouting processes and player development process, we were looking more at high probability players to re-stock our Minor League system, guys who would have a pretty good certainty of carrying value and getting to the big leagues."
As has been the case since 2005, two years after coming over from the Padres front office, Jason McLeod is in charge of drafting the best amateur talent available as the club's director of amateur scouting.
"We put a lot of emphasis and put a lot of responsibility on our scouts," McLeod said. "Coming from San Diego, and knowing as much as I do about a lot of the other organizations, I think we ask a lot more of our guys, in terms of really digging up information, getting information about players, both on and off the field."
After using the Draft to retool the upper levels of the system, including at the big league level, the team has shifted its focus slightly in an effort to deepen the talent pool in the organization.
"As our player development operation has improved, it allows Jason and the scouts to look at players who might be more impactful but carry greater risk because we feel like our environment in the Minor Leagues gives them the best opportunity to improve from the physical, fundamental and mental standpoint," Epstein said.
McLeod and Epstein both recognized the efforts of the scouts, realizing they wouldn't be reaping the fruits of their system without them.
"It's a challenge we put on them and we really believe in what we're doing and that the information that they've gotten to us has been really helpful in the Draft," McLeod said.
So when the Red Sox make their first selection with the 30th pick on Thursday, Epstein has every reason to feel confident.
"That's a good feeling, because there's a lot of uncertainty in the Draft and when you can trust your people and trust your systems and have some continuity, it makes the process go along a lot more smoothly," Epstein said.
Mike Petraglia is a contributor to MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.