A lot of the discussion naturally tended toward Epstein, the Massachusetts native who was making his first public appearance in Red Sox territory since leaving Boston's GM job for Chicago's presidency.
"It's a part of me; it will always be part of me," Epstein said of his former haunt. "I'm not going to try and fake it ... I think we're all allowed one [American League] team to pull for."
Epstein also tried to temper reports that the Sox clubhouse was out of control during September's swoon.
"If you compare the 2011 team to the [World Series champion] 2004 team, they were a bunch of choir boys," Epstein said. "The difference is we won the last game in '04."
Cashman, who has a newly inked three-year deal to stay with the Yankees, was compelled to attend the event after reading Olney's story, while Huntington grew up in New Hampshire.
Cashman joked that the decision to remain in New York's spotlight was puzzling even to him. "I'm working on that with my therapist," he said.
Cashman also said the Yankees are looking at a relatively "conservative winter" as the team pursues pitching: "We've gotten better at adding patience into the franchise. I'm pretty happy with our offense. I don't feel any need to make changes there. But I'm not satisfied with where we are pitching-wise. We're the Yankees. We're going to get connected to every [free agent] out there. But it will probably be a conservative winter."
The possibility that Cashman and Epstein could actually become trade partners now wasn't lost on either man. That's as far-fetched a pairing as there was when Epstein was in charge of the Sox.
According to WEEI.com, Epstein could recall just one instance in which they even discussed a trade. After he became GM in 2002 he suggested to Cashman in passing that the Sox send Shea Hillenbrand to New York for Nick Johnson.
"It was kind of half-joking, half-begging," Epstein said.
"We don't really deal with the Red Sox, they don't deal with us," Cashman said according to the AP. "You don't see Yankees and Red Sox doing business too easily. Unless it's for something like this."
The discussion was followed by an online auction of baseball memorabilia donated by players and teams. The funds raised will go to the Vermont Farm Disaster Relief Fund.