"Yeah, wasn't expecting to see that tonight," Cherington said.
Cherington was at the University of Massachusetts Amherst, along with Neal Huntington of the Pirates and Chris Antonetti of the Indians, for a panel called "Covering the Bases." The event was in celebration of the 40th anniversary of their alma mater's Mark H. McCormack Department of Sport Management.
Just before the panel began, they were talking about the trade.
"Those types of deals are really difficult to anticipate," Antonetti said. "We've talked to both of those teams and had some ideas about different players that may have been in play. But the specifics of it, or mechanics of it, I think we learned about probably about the same time everyone else did."
The Red Sox-Dodgers deal had a similar composition of high priced Major Leaguers being exchanged for young, inexpensive talent. Now, if Cherington helped start some budding trend, he coincidentally has to deal with the repercussions inside his own division.
Cherington said Toronto's movements don't affect his club, however.
"We know we have a plan for this offseason, we're going to see how much we can execute," Cherington said. "I haven't seen whether that [trade] has been confirmed or all the details of it. If that doesn't happen, it's not going to change what our plan is or our ability to execute. We'll have to do that, and we've stated that, and we'll continue to do that."
Although these GMs did not see the deal creeping up in sum, a number of the parts involved did not surprise them.
"Because, as Chris said, you're talking to all the teams, you have a sense for some of the players that may be in play," Cherington said. "Not necessarily those two teams matching up, but not all the names were surprising."
Said Huntington: "A lot of it depends on the magnitude of the deal, the clubs involved. Some clubs are -- the bigger the circle gets, the more likely some things begin to get out. As Chris talked about before, you may have indications that certain players are in play. But some times we get caught by surprise, too."
For Antonetti, watching the Marlins-Blue Jays deal unfold was similar to the experience of watching the Dodgers-Red Sox deal. He had a clue, but not the whole picture.
"We had some, I mean not the specifics of it, but grumblings that there were some some potential deals going on," Antonetti said. "At that point in the year, you're also seeing who's on waivers at different points at time. So that gives you potentially some insight to what players have the potential to move."
The three GMs are close friends, and both Antonetti and Cherington were hired by Huntington early on in their careers. The three have already talked about trades this offseason, and there could be some logical pairings.
If David Ross passes his physical, the Red Sox will have three catchers. The Pirates have one.
Tuesday's event, though, was not about talking shop amongst themselves. They spoke for an hour in an auditorium filled with 750 people, about their time at the school and the climb they took to the top.
"We've all talked already this offseason, I'm sure we will some more," Cherington said. "But we didn't work on any trades in the last two hours."
Said Antonetti: "I'm sure we'll probably have, whether it's later tonight or tomorrow or in the next couple weeks, I'm sure we'll reconnect on some of the trade conversations we've had already."