He just did what a lot of people thought wasn't possible in trading his three highest-paid players -- Carl Crawford, Adrian Gonzalez and Josh Beckett -- the Dodgers for first baseman James Loney and prospects.
Crawford, Gonzalez and Beckett will make almost $60 million in 2013, and even if the Red Sox are picking up some of the money, they'll still be dropping significant dollars from the payroll.
Instead of spending the off-season trying to free up a dollar here and dollar there, Cherington can now give the Red Sox a dramatically different look.
When he's done, they'll will no longer be Theo Epstein's Red Sox. They'll be his.
Here's some advice, Ben.
Pitching, pitching, pitching.
Begin by signing a couple of starters. Throw in a reliever or two.
Oh, and another word of advice: Think short-term.
The Red Sox got into trouble with a bunch of big-ticket, long-term contracts. There appears to be enough veteran pitching help out there that the Sox can fix their problems without making more than perhaps one long-term deal.
In the end, the Sox will rise and fall on the quality of the farm system. This will be the offseason to fill in around the edges and get the Sox competitive again.
Some experts have said this isn't a strong free-agent class. Don't believe 'em, Ben. There's plenty of guys out there that can help.
Kyle Lohse? Yes, absolutely.
Hiroki Kuroda? You bet.
Zack Greinke? Definitely worth a phone call.
Brandon McCarthy and Ryan Dempster should be hearing from you as well. As for the bullpen, Mike Adams would be a terrific setup guy for Andrew Bailey. J.P. Howell is another interesting name. And there are others.
The point is that Cherington will have the financial freedom to start making calls and finding deals he's comfortable with. If he takes two new starters and two new relievers to spring training, he'll probably be feeling pretty good about his team, especially if David Ortiz and Cody Ross are re-signed.
The Rays and A's have reminded us this season that good pitching will cover all kinds of other holes. The Nationals, Reds and Dodgers have also ridden pitching back into contention. The Mariners have had a great second half because of their pitching.
The Texas Rangers are another example. When this season begin, they had so much pitching it didn't seem there was any way they'd need it all.
Three months later, they were so depleted that they're trading for Dempster and signing Roy Oswalt.
The Yankees thought they had too much pitching. There was no way they needed Andy Pettitte. Heck, they probably didn't even need both Phil Hughes and Hiroki Kuroda.
Smart man, that Yankees general manager Brian Cashman. He kept collecting pitchers and has needed every last bit of it.
It's funny how when you've got pitching, when you have the ability to keep your team in the game and not blow leads and all that other stuff, everything changes.
Clubhouse chemistry improves. There might be less drama, and wouldn't the Red Sox love that? Even the manager would get smarter, the sportswriters less annoying. Okay, scratch that last one.
Besides, the Red Sox have a good place to start. In a perfect world, John Lackey will be healthy and productive for the Red Sox in 2013.
Here's predicting that Jon Lester will be terrific in 2013.
Clay Buchholz may be great in 2013, but he took a step back in 2012. He's young and still learning. At least, the Red Sox hope so.
It'll take a few days to digest what your roster looks like in 2013, but the bottom line is that the Red Sox lost one significant contributor from 2012.
Adrian Gonzalez was a rock in the lineup and the clubhouse. He was quiet and consistent, and the Red Sox could have used a dozen more just like him.
He'll be difficult to replace, but with Ellsbury and Will Middlebrooks healthy for an entire season, Cherington can mix-and-match in the free-agent market. That's how the Rays do it.
If the Red Sox don't make another move, they could open next season with:
Jacoby Ellsbury CF
Dustin Pedroia 2B
Will Middlebrooks 3B
David Ortiz DH
Cody Ross RF
James Loney 1B*
Ryan Lavarnway C
Ryan Kalish LF
Jose Iglesias SS
* Loney is a free agent and may not be re-signed.
When fans scream for Josh Hamilton or Michael Bourn, Cherington should remind 'em that Sox starters are 26th in the Major Leagues in ERA and 20th in innings.
There is no rebuilding in Boston. That's just not how it works. The Dodgers are in a different place. They believe Gonzalez can help them win a championship and are hoping a change of scenery is good for Beckett.
In taking on so much money, the Dodgers are telling their fans that a new era of Dodgers baseball is off and running. But their gain is good for the Red Sox. Real good.
Richard Justice is a columnist for MLB.com. Read his blog, Justice4U. This story was not subject to the approval of Major League Baseball or its clubs.