For several minutes in excruciating detail, the man asked Epstein's advice in dealing with a son struggling to make his baseball team. Practicing what he preaches to fans, Epstein patiently listened to someone out there who still thought the Cubs president had all the answers.
"I'd like to help but I don't know the situation,'' Epstein said politely.
Refreshingly, Epstein knows what he doesn't know. As Epstein closes in on 40 next December and distances himself from his rock-star persona in baseball, self-awareness remains the self-deprecating executive's biggest strength. So Epstein didn't dare predict how a 2013 season he framed as a playoffs-or-sell-off proposition will unfold — but interestingly did share his pragmatic plan in case it unravels.
"What I want to avoid is the middle ground,'' Epstein said. "It'd be nice to make the playoffs or get a protected draft pick (awarded the bottom nine teams). We're not hiding that. There's no glory in 78 wins instead of 73. Who cares?
"We're going to see where we are and take a real cold assessment in the middle of the season. If we have a legitimate chance to push for a playoff spot then 2013 can become our primary focus. If we think a playoff spot's not in the cards, there will be no concern for appearances or cosmetics whatsoever. We'll continue to address our future and trade off some pieces that would keep us respectable.''
Consider yourself warned, Wrigleyville. If you thought last September was bad, this could look worse. This could result in a month ugly enough to make rooftop owners want to block their own views.
"Those are the type of things we have to be tough enough to withstand,'' Epstein said. "I hope we surprise some people. There is definitely more talent here than people give us credit for.''
If you believed in baseball Theocracy when the Cubs hired Epstein in October 2011, nothing has shaken that belief. Not 101 losses. Not dumping Ryan Dempster or delays in Wrigley Field renovation. Not anything.
Epstein still has the right answers because he asks the essential question nobody in charge ever dared: Why not try building a winner from the bottom up by revamping the minor league system? If anything has changed about Epstein since he arrived in Chicago billed as the savior, it might be the 39-year-old has become less guarded and even more introspective as he embraces the city's "Midwestern sensibility.''
That term came up during an easygoing conversation when Epstein explained why Cubs fans readily accept sacrificing seasons in the name of winning in 2015. Why can Epstein get away with placing minor league development ahead of major league success in a major market?
"We're being transparent and they're responding by giving back faith, belief and energy,'' Epstein said.
Credit fans who enjoy watching young players grow up and the Cubs' failure to win the other way by investing in overpriced free-agents, Epstein reasoned. It says everything about the state of the Cubs that the highlight of Epstein's tenure came last fall in Arizona when he attended an instructional league workout and finally detected "The Cubs Way.''
"It was really invigorating,'' Epstein said. "I know this sounds silly coming off the year we had but we are really clicking on all cylinders in scouting and player development.''
Baseball America agrees, ranking four Cubs prospects among the game's top 100. One baseball executive projected the Cubs could have six by next spring. Everybody in Cubdom has heard of phenoms Jorge Soler, Albert Almora and Javier Baez. Most days, Epstein stares at his computer watching video of minor leaguers in search of the next Starlin Castro or Anthony Rizzo.
Speaking of Rizzo, Epstein invoked his name during one of those intermittent bouts of introspection. Apparently trading for Rizzo, a former Red Sox draft pick, represented one of two things every new executive does after taking over a team.
"Typically, they make a pretty good trade with a player they're familiar with (Rizzo) and, two, they'll screw up a trade because they won't have the first-hand knowledge you need with some players in their own organization,'' Epstein said. "We definitely did that.''
The rare mistake Epstein admitted came in December 2011 when the Cubs traded outfielder Tyler Colvin and infielder D.J. LeMahieu to the Rockies. Another happened when the Cubs left Ryan Flaherty unprotected in the Rule 5 draft and the Orioles signed the second baseman, who started in the playoffs.
"We fell into some familiar traps,'' Epstein said.
They will fall some more, Epstein acknowledged. But the encouraging difference in Epstein's regime is he focuses less about the Cubs getting up than staying on top once they do.