Cherington wanted players with grit. OK, that's a cliche, but still. He wanted players at a certain point in their careers, players who would put the team first, players who would set a tone in terms of expectation and professionalism.
And that's how Jonny Gomes, Shane Victorino, Mike Napoli, David Ross and Ryan Dempster came to play for the Olde Towne Team during the offseason. Cherington filled holes in his lineup, but he filled that hard-to-define thing that really good teams have. Among other things, it's work ethic and focus and a commitment to one another.
Those of us on the outside may never fully grasp it, but those on the inside absolutely do. As A's outfielder Seth Smith said in Spring Training, "I never fully understood leadership in baseball until I watched the work that veterans like Jonny Gomes and Brandon Inge did with our young guys last season. They set a tone in terms of professionalism, and our young guys knew to follow."
Cherington had already taken a huge step in that direction with the hiring of John Farrell as manager. Farrell carries himself with a certain presence, and because he'd been there as pitching coach and because the veterans trusted him and respected him, he was an absolutely perfect fit.
When all was said and done, the Red Sox were changed in a way a lot of people didn't think possible. Dustin Pedoria is their leader, and these Red Sox play the game with some of his energy and determination.
Other things are easier to measure. Because veteran right-hander John Lackey is again a front-of-the-rotation starter, because young lefty Felix Doubront has taken a huge step forward in his development, the Red Sox have gotten enough starting pitching to spend 103 days atop the American League East.
Even with injuries to right-hander Clay Buchholz and closer Andrew Bailey, even with left-hander Jon Lester struggling at times, the Red Sox are a cool 20 games over .500 at 64-44 and nicely positioned to make the postseason for the first time since 2009.
Their real need would seem to be in the bullpen, but with the uncertainty surrounding Buchholz and with this entire season becoming an opportunity to make a championship run, Cherington finalized a deal to acquire Peavy from the White Sox in a three-team deal also involving the Tigers late Tuesday night.
It's a fascinating, logical trade on so many levels. The Red Sox add quality and depth to their rotation in Peavy. Meanwhile, the Tigers begin preparing for the possible Biogenesis-related suspension of shortstop Jhonny Peralta by acquiring Jose Iglesias from the Red Sox.
Iglesias came up as a shortstop and is most comfortable there. But he's played a lot of third base this season, and until his bat went cold during the last month, he was very productive.
Finally, the White Sox acquired one of the Tigers' best young players, 22-year-old outfielder Avisail Garcia, as they continue rebuilding. In one deal, three teams filled needs.
It's a trade not without risks. Iglesias is 23 years old. He's hitting .330 despite batting .200 in July. With Peralta likely gone from Detroit after this season no matter what, Iglesias could turn out to be a cornerstone type of player.
Peavy, 32, has struggled at times to stay healthy and has been hit hard a few times this season. But don't sweat the small stuff. In making this deal, the Red Sox are sending their players a message that management believes in this team and is going to try to give it every chance to win.
They're getting the right guy, too. Peavy is an old-school warrior, a guy who has had enough serious injuries that he's thrilled for every single day he still has in the game. He's relentless in his preparation and approach.
Peavy will give the Red Sox quality innings and will be unflappable in the pressure of a pennant race. While the Rays have rushed to the top of the division with baseball's best rotation, the Red Sox made their own rotation better and deeper with this deal.
To have Lackey, Lester, Peavy and Dempster in one rotation is to convene the graduate school of pitching. At their best, they're a rotation comparable to any in the game. When they're not at their best, they're smart enough and competitive enough to figure out a way.
For these last few weeks, the Red Sox have resisted discussing their best young prospects, and Iglesias certainly qualifies. On the other hand, sometimes seasons evolve into chances to do something special.
In Boston, where the standard is high and the fans savvy, this trade will probably be seen as both painful and necessary. Iglesias may go on to have a spectacularly successful career, but the Red Sox weren't about to let this opportunity pass. Nor should they have.