Cherington did extraordinary work a year ago in signing seven mostly unheralded free agents and assembling a worst-to-first club that won the World Series.
Having done that, the easiest thing he could have done this week would be to stay the course even as the club settled into last place. Apply a bandage here, some glue there.
Cherington could have said all the right things about believing in the boys and giving things a chance to work out. Would have made some sense, too.
Instead, Cherington did what only the really good ones do. That is, he saw his club for what it actually is rather than what he'd hoped it would be.
Cherington saw a club that badly needed more offense, especially more power from the corner outfielders. Cherington also didn't see how he could obtain it without doing something dramatic.
Free agency? Nelson Cruz would be one option this offseason, Melky Cabrera another. To think he could land both of them didn't seem reasonable.
In Cherington's mind, he might have seen doing nothing as tantamount to conceding the 2015 season, which he is unwilling to do.
Cherington could see potential in every other area of the team. Maybe Will Middlebrooks and Xander Bogaerts can anchor the left side of the infield for a decade.
Maybe young catcher Christian Vazquez is the real deal. And pitching? The Red Sox have power arms stacked in their system. Henry Owens and Allen Webster. Brandon Workman and Anthony Ranaudo.
In that way, the Red Sox are the envy of baseball. All those arms allowed Cherington the leverage to shore up other areas.
Yet doing so meant changing the fabric of a club nine months removed from winning the World Series.
Still, Cherington didn't hesitate. With a series of sweeping trades, he dealt away his two best veteran starters, Jon Lester and John Lackey, for offense.
When Cherington was done, he had new players dotted up and down his roster. Primarily, though, Thursday was about getting a pair of corner outfielders -- Yoenis Cespedes and Allen Craig.
If Cherington is right about them, the Red Sox have a chance to bounce all the way back into contention in 2015.
If he's wrong, at least Cherington will have tried. At least he didn't sit on his hands. Wouldn't you rather have this kind of general manager?
Cherington could have gone for younger players, but he preferred Major Leaguers, because he believes the Red Sox can be right back in the mix in 2015.
"We wanted to really give ourselves a head start on building again and becoming as good as we can as quickly as possible," Cherington said.
In dealing Lester to the A's and Lackey to the Cardinals, Cherington left the Red Sox without a proven starter.
Clay Buchholz potentially could be the guy, but he has had trouble keeping his ERA under 6.00 this season. All the other Red Sox starters combined have a total of 40 big league starts.
They've all dominated the competition in the Minors. All of them are projected to be solid big league starters.
But Lackey and Lester are not projections. They combined to pitch 402 innings in the 2013 regular season and go 7-1 in the postseason. There are easier things in baseball than replacing that kind of quality.
Still, Cherington took this bold step, and good for him. He's hoping that Craig will rediscover the mechanics that made him an All-Star last season for the Cardinals and that Cespedes will team with David Ortiz to give the Red Sox a big-time power presence in the middle of the lineup.
If that happens, everything can work outward from there. There's less pressure on Ortiz, less on Dustin Pedroia, more balance top to bottom.
Thus begins the next chapter of Red Sox baseball. During these final two months, the Sox hope to find out if Middlebrooks and Bogaerts can handle third and short, respectively, and where super rookie Brock Holt might be the most productive.
"These are now the most important 54 games of our season, because we've got a lot to find out," Cherington said. "We need to start building a team again. We've got to start building a team that can win."
The Red Sox are 12 games under .500 and may very well wrap two last-place finishes around last season's championship.
But Cherington moved aggressively and fearlessly to begin work on 2015. If veteran pitching is needed, it's available in free agency. In that way, the Red Sox may be able to cover the loss of Lester and Lackey.
And if Lester actually re-signs with the Red Sox, they'll be positioned to contend again. They may be there anyway. If nothing else, Cherington pushed them a couple of huge steps in the right direction.
"I think we're in better position than we were a week ago," Cherington said. "We're happy with what we did."