Furiously awful lead in his article
http://www.providencejournal.com/sports/20170630/red-sox-release-allen-craig
1) We needed to trade Lackey, and this was the best deal
2) Joe Kelly has probably been the best guy in the bullpen this year not named Craig Kimbrel
Except:
1. Cherington specifically said they took Craig and Kelly over prospect packages because they were rebuilding on the fly, which was absurd given how the actual rebuild of this team from his 2014.
2. Taking just Kelly and not Craig at all would have made this a better deal. Funny thing is at the time I basically called this deal exactly as it played out: Craig was a flier who wasn't likely to pay off and Kelly's real value was in the bullpen. But Cherington wasted two years of team control letting him fail as a starter.
3. Getting literally any of the then prospect OFs that St. Louis didn't expect to have playing time for out of Piscotty, Grichuk, or Pham would have had them substantially better off. In fact, Pham was resigned as a mLFA the year before and the Cards didn't think he'd ever amount to much. He's now looking like the best of the three. Funny enough he's a guy I said the Sox should have been trying to get in this exact deal. A Pischotty/Grichuk + Kelly + Pham deal would have actually been pretty viable from St. Louis' perspective and would have completely removed the need to sign Rusney Castillo.
To summarize: Ben went into the trade market with a clear need for young OFs while Bradley was in the middle of his .531 OPS campaign and Betts was only just on the verge of being ML ready, no other OFs worth mentioning were on the entire ML roster. He had an asset the Cardinals needed. The Cardinals had the most organizational OF depth in all of baseball at the time with the three mentioned above in the minors along with super prospect Oscar Taveras, Matt Holliday under contract through 2016, and Jon Jay and Peter Bourjos under team control through 2015. They also had John Ramsey who they'd traded just the day before to Cleveland for Justin Masterson, a deal they'd likely have changed/not made if needed to get the clearly superior and longer controlled Lackey. He comes away with the guy with the big money contract, the nosediving production, and a lingering foot injury that basically assures he's no longer really capable of playing the OF.
This when the entire city of St. Louis (I lived there at the time) still loved Allen Craig, putting local PR firmly on the side of them moving an unkown prospect from Memphis over him.
This might be the worst GM move of Cherington's career, and that's by the guy who signed Castillo, Sandoval, Hanley, and Porcello, traded Reddick for Bailey after Reddick had hit ML pitching for nearly half a season, and who traded Lester for another short term fix in Yoenis Cespedes, who he then flipped the next winter, only to see Cespedes produce like one of the best power hitters in all of baseball since leaving Boston. Oh, and if instead he'd just kept Cespedes until mid-year instead of trading him in the winter the return would have been Michael Fulmer instead of Rick Porcello.
But still Lackey for Craig + Kelly was a worse deal, because all the rest could be explained away as market dictated values and making the moves needed to fill the holes on the roster (even if he created a good number of them himself). Lackey for Craig + Kelly was a downright bad deal the day it was made and the only value we've extracted from it was produced by doing exactly what Cherington didn't attempt the entire time he still had the ability to do so - moving Kelly to the bullpen.
