Unquestionably, working his way up the ladder was difficult, but the 37-year-old Cherington had no hesitation when asked about the most difficult challenge of his career.
"[I'm] still trying to get through it," Cherington said to laughter from the crowd of 750. "[It was a] tough year in Boston, and I think we really are still trying to get through it. But I think what we've learned is ... you have to fall back on the things that you can count on the most."
Trust was a theme in almost every discussion during the hourlong panel, which also included Neal Huntington and Chris Antonetti, the GMs of the Pirates and Indians, respectively.
"I know when I call Chris or Neal that we may disagree about something, but I know I trust them," Cherington said. "And I know I trust what they're telling me. At the end of the conversation, it might not lead to a deal, but I know the information I'm getting is accurate. They're being honest. The more relationships like that -- whether it be with another GM, or an agent, or one of your owners or a player, whatever -- the more relationships like that, I think the better chance you have of making successful decisions."
The three can also rib one another, even publicly. When a question about selecting a manager arose, Cherington, sandwiched between his counterparts, got stares from the two, and more laughs from the crowd, as a nod to the Bobby Valentine travails.
The Red Sox have the cleanest slate to work from, in terms of salary commitments, in a long time. As Cherington reloads following a 69-93 season, he has money to play with, and like everyone else running a team, a philosophy for dealing with agents. What's rare is having a public forum in which to explain that philosophy.
In well-functioning relationships, GMs and agents are really on the same side.
"You have to protect your own interests, you have to protect the team, and you're trying to do something for the Red Sox," Cherington said. "Once you have a player in your organization, there's a common goal. When you're negotiating over a player, you may have disagreements as to what's right and what's wrong, and what's fair and what's not, and you're just trying to get a deal done. But once a player is in your organization, you really want the same thing. The best outcome for everyone is for the player to succeed. That helps the team, it helps him eventually earn more money and it helps the agent get a bigger commission."
The agents who remain hands-on with their players after the negotiations are over are the ones Cherington values the most.
"My feeling is that the best agents are the ones that really grasp that. Once the player is in your organization," Cherington said, "they're as committed as you are to making sure the player does what he needs to do off the field [and] on the field to get the most out of him."
Overlooked by most is how much GMs have to deal with outside uniformed Major League personnel. For example, the Red Sox recently restructured their medical staff, naming Dr. Laurence Ronan as their medical director.
That part of the job is actually fun, too. And seriously time-consuming.
"Some of the actually more enjoyable parts of the job have nothing to do with [players]," Cherington said. "It's finding the right guy to scout in the southeast. It's finding the Minor League free agent that no one has ever heard of who ends up helping. ... It's finding a better way to structure our medical staff -- the things that are not quite as visible that we know in the long run make an impact. We spend a lot of time on those parts of the job, just as much on those parts of the job as trying to make trades or sign free agents. Maybe not today [during the height of free agency], but most parts of the year."
When Cherington talked about people he can count on the most, first was his wife, Tyler Tumminia, who also works in sports. The two celebrated the birth of their first child this summer. GMs take it personally when a team loses, and having family support is necessary.
If there are no stable voices in your corner, correcting problems becomes a lot harder. Like closers when they blow a save, GMs need people who can put blinders on the next day and get the necessary work done.
"My wife's a big part of that," Cherington said. "The people that you work with, that you trust and you know have your back, show up every day and go to work and try to figure this out. We're fortunate that our ownership group in Boston is fully committed. So when you have those things in place, we try to see through the fog and get to the things that will get us back on track as a team.
"[It's] hard to watch it when things aren't going well, so we take it personally when things aren't going well. We ... put it on ourselves to get it pointed in the right direction, and we need to do that in a way that works over the long term. That's one of the biggest challenges: 'OK, what have we done wrong? How do we fix it?'"