The visitor had attempted to lounge around the session unnoticed. Upon being acknowledged, he quickly challenged the Red Sox general manager with the toughest question of the week.
"How many games are you going to cost the team as the new general manager?" Cubs president of baseball operations Theo Epstein shouted.
"I already cost them," Cherington said with a smile.
For a brief second, it was a Red Sox reunion. But after a successful nine-year run as general manager in Boston, Epstein is starting anew in Chicago and slowly easing into to his new position.
Emphasis on slowly. Since Epstein commutes constantly from Chicago to Boston — where he still has family – he joked that he's been hounding Cherington to return some favors back his way.
"I'm still working out of [the Red Sox] office like once a week," Epstein said. "I set up at Panera down in Brookline Ave. and I was calling Ben begging to let me use my old office. He didn't answer, so I broke in. I know the interns."
Along the way, the former Red Sox general manager made his first move for the Cubs, inking outfielder David DeJesus to a two-year deal.
Then there's that case about compensation on his agenda. Since leaving Boston for Chicago on Oct. 22, Epstein and Cherington have pushed those negotiations to the backburner. On Thursday, the issue continued to linger on.
"We've loosely defined a strategy of talking at some point in the near future," Cherington said. "We'll resolve it at some point, I'm sure."
During the winter meetings, Epstein split his responsibilities with general manager Jed Hoyer. Like Cherington, the Cubs' brass departed from Dallas quietly, only selecting pitcher Lendy Castillo in the Rule 5 draft.
The difference, of course, is Epstein has a defined legacy, patching together two championship teams. Six weeks into the job, Cherington is still working to piece together his own masterpiece.
But Cherington's challenges aren't much different from Epstein's in 2002. Both transitioned in Boston with the responsibility of surrounding a star-studded cast with capable role players.
"I feel like we have a really good team that just needs complements and needs to be put in a better position to win over a six-month stretch," Cherington said. "That's what we're focusing on."
As for getting Epstein off his case? Well, that's a tougher task.
"He's like an old pair of jeans," Cherington said. "He just keeps showing up."
