A few made an earnest attempt, a few laughed and a few blushed, embarrassed that they couldn't come through.
"I owe you one," one higher-up told him.
But Theo, of course, wouldn't have pulled this little stunt if he, himself, had nothing to offer. And so there was the newly crowned king of the Cubs -- Yale-educated, Boston-bred and, now, Chicago-credentialed -- busting out his best attempt at a Bulldog ballad.
Thus began the Epstein era on the North Side. One man singing loud and proud, hoping those around him will one day be singing the same tune.
This is a tall order that Epstein, introduced as president of the Cubs on Tuesday afternoon at Wrigley Field, has inherited. He now finds himself at the helm of a ship well past sunk. The history here is at times tragic, at times comical and, like all things true to life, most often a little bit of both.
That 86-year aridity Epstein helped erase in Boston? Child's play. Heck, 16 years before Theo was handed the Red Sox's general manager's reigns, Boston had been a half-inning away from a World Series title.
Would that the Cubs could come so close. The last time they were even in
the Series was mere months after the U.S. had dropped a bomb on Japan.
Yeah, it's been a while.
And at least the Red Sox's "curse" -- if such a thing exists -- could be tied to a human being. A Hall of Famer, at that. Cubs fans have a lowly goat and, in particularly pitiful moments, an unfortunate fan named Bartman to blame for their misfortune. And only because that's more fun than simply pointing to the many missteps and mind-blowing bumbles that have paved the way to more than 100 years of futility.
Remember that one of Epstein's predecessors in such an appointment with the Cubs was E.R. "Salty" Saltwell, who, prior to being named the GM in 1976, had been serving as the club's concessions manager. If we look at this from that perspective, Theo doesn't exactly have a high standard to live up to here.
But he does enter with enormous expectations, given the reputation he's earned as a true buster of ghosts. It's why, in the weeks leading up to this official unveiling, reporters staked out Starbucks hoping for a sight of him after a hot tip (one Epstein acknowledged to be accurate), why "Welcome Theo" signs run rampant around Wrigley and why the merchandise store across the street from the famous marquee is selling "Epstein 12" jerseys (with Alfonso Soriano left to wonder how the new guy stole his digits).
Epstein is aware of the savior status he's been branded with, unfair as it might be. He'll do his best to temper emotions and expectations around here, but the fact that Tuesday's presser was the most exciting event at Wrigley in at least three years is telling, in and of itself.
"I should probably have another press conference right now to resign," Epstein joked, "because my popularity is definitely going to be at an all-time high right now."
It will undoubtedly dip at the first misfire, major or minor. Sports fans are inherently insatiable. And Epstein, even with the bling of two rings, is no stranger to slipups. Or haven't you heard about the Carl Crawford and John Lackey contracts?
In an effort to improve the percentages, Epstein is expected to execute the baseball equivalent of getting the band back together. Once an adequate compensation package is agreed to, he'll import Padres GM Jed Hoyer and his assistant, Jason McLeod, reuniting three men who made magic near the Back Bay Fens. And with his elevated assignment as president, with Hoyer and McLeod in charge of the day-to-day, Epstein will have the opportunity to take a broad-based approach to an organizational overhaul that will encompass both the baseball and the business sides.
As is typical in sterile press conference settings, Epstein talked about these things in grand generalities - careful, of course, to note that a GM move has not yet been made and that Mike Quade's status has not yet been decided. He talked about building a foundation rooted in scouting and development for the long-term while also trying to craft a contender in the short.
But Epstein knows, in his heart of hearts, that the work that must be done to make the Cubs a contender is inherently more intricate than the situation he inherited in Boston. The 2002 Red Sox won 93 games and had Manny Ramirez, Johnny Damon, Jason Varitek, Nomar Garciaparra, Pedro Martinez and Derek Lowe all at prime ages. This Cubs team, on the other hand, lost 91 games this year, encumbered by the weight of unwieldy contracts and underachievers.
"In Boston, my first year there, we took the payroll down 10 or 12 million dollars or so and improved the team on the field," Epstein said. "That doesn't happen every time. The big thing in Boston was we had a great core when we first got there. We had future Hall of Famers on the roster. But we also, I think, did a pretty good job and got really lucky those first couple offseasons. We hit on every player -- David Ortiz, Bill Mueller, Kevin Millar, Curt Schilling, Keith Foulke, Mike Timlin, guys like that. Those players, along with the core that we inherited, put it together on the field. That doesn't recreate itself all the time."
No, it does not, which is why the foundation is the most important element of all. The Cubs made great strides in that department with an aggressive Draft and Latin American approach this summer, and that's one of many facets of this job that caught Epstein's eye.
As far as resources are concerned, Epstein has a lot to like here. The Cubs' drawing power is owed to the allure of its home park, and that pumps blood into the payroll. But further efforts to maximize that advantage can and must be made, much in the same way the Red Sox successfully refurbished Fenway Park for the current century. Get it right on the baseball and the business side, and the Cubs could be a premier powerhouse. Imagine that.
That's what excites Epstein. That's what has him singing.
"After 10 years [in one place]," he said, "no matter how passionate you are, you see the same issues day after day, you're around the same people day after day, you have the same landscape day after day. Eventually, you'll benefit from a new landscape, fresh problems. The goal for the individual is to have some re-invigoration, some rebirth. And I certainly feel that. I feel energized."
He doesn't yet feel the weight of 103 years of history. Maybe he never will.
"I don't believe in curses," he said.
That's the message Theo Epstein brings to Wrigley. For now, he's a soloist singing an old college tune. But someday soon, he expects to be making sweet music with the many faces comprising the Cubs.