The Yankees general manager was invited to the home of his arch-rival and the team that has won two World Series titles in the last four seasons by his Boston counterpart Theo Epstein to help the Red Sox general manager promote the "Hot Stove, Cool Music" concert on Sunday night in Boston.
"I live in Connecticut," Cashman said. "It's not a far drive. I was asked if I would be interested in coming up and spending a little time here. So it was a lay-up. I hope everyone had a good time."
Cashman was one of the featured speakers on a panel that included Epstein, Blue Jays general manager J.P. Ricciardi and baseball luminaries Bill James, ESPN's Peter Gammons and agent Scott Boras.
"Based on the Northeast, from New York through Maine, these people live and die every day with their teams," Cashman said. "The passion is there. I'm not surprised. It's great to sit down with people like Theo, J.P., Peter and Scott and Bill James, who I don't have a chance to talk with much at all, but I certainly know him through his writings over the years. So that was a treat."
Everyone in attendance wanted to know the status of the Johan Santana talks after Hank Steinbrenner told the Associated Press that he is "leaning toward" going through with a trade for the two-time A.L. Cy Young winner.
"Mostly, especially in our big markets, you get challenged on the short-term stuff so much you can make a mistake if you get caught up in the winds of the pressure of making a [trade]," Cashman told the audience.
"Like right now, the Red Sox and Yankees, at least, are in the middle of this Johan Santana stuff. What's the right thing for the now? What's the right thing for the future? These are the wrestling matches that go on in the organizations and you have very spirited conversations about what's right and what's wrong."
Cashman said he still believes in a strong and productive farm system.
"At the end of the day, if you have an opportunity to build something and be a leader in that situation, you stick to it. It's your way and you find a way to stick to it, despite the media pressures, the ownership pressures, the fans' pressures and realize, 'You know what? I believe in what I'm doing and I'll stick to it as long as you give me the opportunity and then get judged on the results at the end of the day.'"
Following the panel discussion, Cashman fielded questions on everything from dealing with the Steinbrenner brothers to Roger Clemens and the Mitchell Report.
"Everybody has their own style," Cashman said of the Steinbrenners. "And Hank has obviously taken charge on behalf of his father, along with his brother, Hal. They have different styles. Hal is more quiet and Hank is very available, but my job is to continue to line up the structure of the organization that can find the amateur talent."
On the eve of Clemens' interview on "60 Minutes," Cashman offered his perspective on what to expect from baseball going forward from the Mitchell Report.
"All of it's difficult," he said. "There's no doubt about that. It is what it is. The Mitchell Report came out and there was some shocking information that was in there, and now we're seeing it play out after the fact and what you have to do, unfortunately, is sit back and watch it unfold."
Peter Gammons said Cashman is weathering yet another storm in New York.
"Brian Cashman faced a lot because the Mitchell Report was so based on basically two sources, both out of New York. There were a lot of New York names in there," Gammons told reporters. "I think the more we have to deal with Clemens and Bonds under oath, it takes away [from baseball]."
Cashman told the hundreds of fans in attendance and media afterward that the most successful general managers stick to a game plan, in good times and bad.
"You're not going to always be right, but in the end you have to stick to your convictions and then you get judged on the results in the end, for better or for worse," he told the audience.
Mike Petraglia is a contributor to MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.