But in terms of overarching, big-picture items, he will forever be held to his spotty success with free agents and the way in which he left the farm system as a bottom-heavy one offering little help for the big club.
The first item has been discussed for years, or ever since J.D. Drew hit his first weak grounder to second base while wearing a Red Sox uniform. In addition to Drew, Epstein has given a lot of money to players who haven't completely worked out. Among the current players are John Lackey, Carl Crawford and Bobby Jenks, although Crawford has loads of time to make good.
Epstein admitted to some cracks in the system when it comes to free agents.
"When speaking about things that aren't exactly the way we want them to be in this organization, our decision-making process on expensive free agents, big-ticket free agents, has not been satisfactory," he said the day after the season came to an end. "Not at all."
However, any team with money to spend is going to throw it in the wrong places from time to time, and not every Epstein maneuver was entirely his. What was his was a concerted mission to build an organization from the ground up, one that supplied Fenway Park with the fruits of a fertile farm system.
He had incredible success in this venture, drafting and producing the core of today's team: Dustin Pedroia, Jacoby Ellsbury, Clay Buchholz, Jonathan Papelbon, Daniel Bard, Jed Lowrie.
Yet, upon his departure, Epstein has left the cupboards a bit bare, at least at the very top. Since Bard made his big splash in May 2009, nobody has made the leap from the farm to the bigs and stuck.
The trade for Adrian Gonzalez was a huge factor, thrusting from the fold two top-of-the-system studs in Anthony Rizzo and Casey Kelly and an electrifying young outfielder in Reymond Fuentes. Epstein got the player he coveted for years, but he tore into his stash of high-end talent, once considered among the most bountiful in the business.
Among those that remain, there is plenty of promise. However, not many of them made significant strides in 2011 and the top end of Boston’s system is left somewhat lame.
Ryan Kalish was hurt for most of the season. Jose Iglesias had his own injury issues and still had the look of a player that needed a bit more seasoning. Lars Anderson had a nice second half, but has yet to put up any eye-popping numbers at the Triple-A level.
The relative dearth of high-level pitching talent was on full display down the stretch, when Kyle Weiland — a solid righty, but not a blue-chipper by any stretch of the imagination — was forced to make critical starts for a fading club. Had Felix Doubront not taken a step back in 2011, some of those starts might've been his.
The most help the club received from the Pawtucket pitching staff came in the form of older arms just looking to land a job: Rich Hill, Alfredo Aceves, Andrew Miller, Scott Atchison.
If not for the major strides made by catcher Ryan Lavarnway and third baseman Will Middlebrooks, this scenario would be more striking.
In the 2010 first-year player draft, Epstein had four of the top 57 picks, and this year he had four of the top 40. That flood of talent joins a pretty good collection of players at the lower levels that may one day stabilize the system. But as Epstein leaves town, his "scouting and player development machine" is in need of some repair.