Looking Back on Ben Cherington’s Time as Red Sox GM

After that disastrous September 2011 that was filled with stories of fried chicken, beer, and a terrible clubhouse atmosphere, Ben Cherington stepped into a situation that would seem so enviable to some – a big market team with lots of dollars to spend and a love of advanced stats – but subpar to others because of the long tenured contracts that the Sox had and the aforementioned culture problems.

Let’s look year by year at his important transactions, starting with the winter before the 2012 season and any moves made during the year.


  • Hired Bobby Valentine
  • Traded Jed Lowrie and Kyle Weiland for Mark Melancon (more on this in the 2013 section)
  • Traded Josh Reddick and others for Ryan Sweeney and Andrew Bailey
  • Signed Cody Ross
  • Traded 2011 overachiever Matt Albers and Scott Podsednik for Craig Breslow
  • Executed the humongous trade with the Dodgers that sent Gonzalez, Crawford, and Beckett (and Nick Punto, haha) out west for Ruby de la Rosa, Allan Webster, and others.

I’m ok with these results, mainly because of the Dodgers trade of course.  Cherington realized that the team had to move away from guys like Crawford and Beckett, and the clubhouse needed some fresh blood.  John Henry and co. weren’t gonna let Cherington spend an unlimited amount.  We all know that trade was great, and signing Cody Ross and getting Craig Breslow worked out well also.  But the Reddick trade definitely misfired, although he couldn’t have predicted an injury to Bailey, and the Bobby Valentine signing deserves to be on Cherington’s record forever, even if Valentine wasn’t the first choice.


  • Signed Ryan Depmster (I started off with him to get the bad one out of the way early), Jonny Gomes, Shane Victorino, Mike Napoli, Koji Uehara, Stephen Drew and David Ross.
  • Made a small trade for Mike Carp — I still have no idea who he traded for Carp and honestly it doesn’t matter enough for me to look it up
  • Traded Mike Aviles and others for John Farrell
  • Traded Mark Melancon and others to Pittsburgh for Joel Hanrahan and Brock Holt as a throw in.

A++++++++++.  Nothing else needs to be said. Even the Melancon trade, which looked horrible in 2013 because they had sold low on Melancon and bought high on Hanrahan, has worked out because of Brock Holt.


  • Didn’t offer Saltalamacchia the $14.3 million qualifying offer and replaced him with AJ Pierzynski.
  • Let Ellsbury walk to the Bronx for an obscene price.
  • Botched the Lester negotiations in Spring Training, offering him $70 million over 4 years.
  • Then traded Lester and Gomes for Yeonis Cespedes once the team was done by July.
  • Traded John Lackey for Joe Kelly and Allen Craig.
  • Traded Andrew Miller, who was an upcoming free agent just like Lester, for E Rod.
  • Signed Rusney Castillo for 6 years $72 million.


  • Signed Hanley and Pablo to huge contracts that have… um… not worked out so far.
  • Traded Cespedes for Porcello
  • Signed Justin Masterson and traded De la Rosa and Webster for Wade Miley.

And this is where it really makes sense that he’s gone.  Technically, he chose to not be GM anymore, but DOmbrowski was given more control of the actual baseball decisions and Cherington didn’t want a reduced role, which he seemed to deserve after these moves.  What I don’t get is how much emphasis the Red Sox put on guys who really wanted to play in Boston and really wanted to be part of a great team culture, which Cherington admitted the team tried to do in 2013, only to go against it in the following seasons.  Sign a bunch of buy low guys who loved playing here and cared a ton about the clubhouse environment and win a World Series because of it?  Great, now sign free agents who might not fit either in the clubhouse or on the field in terms of position, as with Hanley.

And Cherington should get wayyyy more blame than he does for the Lester signing.  I’d much rather have Lester than Pocello anyway.  Even when you get past age, team control, and cost, the Red Sox screwed up their dealings with lester massively, not once but twice.  Lester was willing to listen a year and a half ago to extension offers, but hung up the phone when they lowballed him right after coming off an amazing postseason performance from their ace.  Error 1.

And according to what Dustin Pedroia, Lester himself, and others have said, part of Lester’s decision to sign with the Cubs this offseason was about the fact that he had already played for another team.  Lester wanted to be the kind of guy who stayed with one franchise through thick and thin and only had 1 team on the back of his baseball card when he was done.  When they traded him, that lure was all gone, making it much easier for him to leave.  That’s been said, Pedrioa saying it the most explicitly in a few different mediums, which I can find for anyone who wants to see the proof.  (I remember Pedey saying it in an interview, and he was one of Lester’s closest friends, I just can’t remember exactly where.  But I’m more sure about it than I am sure that I hate the Yankees.) So Lester left because they traded him instead of riding out the season and re-signing him, indicating they didn’t know how their ace’s mind worked.  Error 2.

A few times, especially with Lester, it seemed like Cheringotn was trying to outsmart himself.  That’s the main negative that I’ll remember from his tenure.

But of course, that stretch in the 2013 offseason where he got so many useful guys who stepped up all season long, as well as manager John Farrell, deserves to be at the top of his legacy here in Boston.  Professional sports are about championships after all, and those moves he made brought us one.  So thanks for the memories, Ben Cherington.  I’m ok with it being time for you to go, but you brought us a title for which I’ll always be grateful.

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