Ben Cherington Could Be On Pirates’ Front Office Radar

On August 18th, the Red Sox somewhat surprisingly hired ex-Tigers GM Dave Dombrowski to be the new President of Baseball Operations. Their current GM, Ben Cherington, could have stayed on but instead resigned his position. Perhaps it was an ego-related move or perhaps he felt threatened that his power would be diminished or his decisions second-guessed by Dombrowski. Or maybe he saw the writing on the wall after three last place finishes in four years (with one World Series title in 2013, don’t forget!).

Cherington instantly became one of the top “free agents” among front office candidates for subsequent GM openings. It appears that Seattle could move on from Jack Zduriencik. The Los Angeles Angels have Bill Stoneman installed as an interim GM after Jerry Dipoto quit, but since Dipoto was brought on by Cherington as an advisor to the Red Sox, you have to figure that Cherington has been warned about that situation. Milwaukee will be searching around for a new GM and want a young, analytical mind in the decision-making seat. Cherington, age 41, meets both criteria. The Reds may or may not dismiss Walt Jocketty. Philadelphia is almost assuredly canning Ruben Amaro, Jr.

But what if those teams all go in different directions? Maybe they see Cherington’s tenure from 2012-2015 and see just those three last place finishes. Maybe they see the terrible free agent signings this past offseason of Pablo Sandoval and Hanley Ramirez, coupled with the as-of-now disastrous extension to pitcher Rick Porcello.

But what if Cherington himself doesn’t want to jump right back in the hot seat of a franchise? Heavy is the head that wears the crown, as the axiom goes. Maybe Cherington, in his quietest of moments, realizes that he isn’t cut out to be a GM. Perhaps his ceiling is as an assistant GM that can focus on one facet, like player development or scouting. This is where the Pirates can enter as a dark horse for his services.

Both Cherington and GM Neal Huntington are native New Englanders — Huntington and Cherington are both from New Hampshire. Both of them attended (at different timelines) and graduated from Amherst College, a small private college that has produced an outsized number of Major League GM’s. In addition to Huntington and Cherington, Orioles GM Dan Duquette is the third graduate of Amherst that is a general manager. For a school with a undergraduate class of about 1,700, it’s impressive that up until last week 10% of all Major League GM’s were alumni.

Huntington and Cherington appear to have had a good working relationship, as they teamed up on three trades during Cherington’s four-year tenure, including the big trade of Joel Hanrahan/Brock Holt for Mark Melancon/Ivan de Jesus/Jerry Sands/Stolmy Pimentel in December 2012. That trade locked down the back end of the Pirates’ bullpen during this run of excellence of the past three seasons.

Baseball is a network of relationships. If Neal Huntington wanted to bring another strong, analytical voice into Federal Street, it’s not inconceivable that he would help up a fellow Amherstian (I have no idea if that’s an actual term or if I just made it up). A position could be carved out for Cherington where he acts as a liaison between the analytics department headed by Dan Fox and Huntington. Or maybe he could further develop analytical models for minor leaguers. Or maybe it would be a different tack altogether.

Of course, all of this spirit of camaraderie could also apply to Cherington being hired by Dan Duquette with the Orioles. Duquette originally hired Cherington in 1999 when he was then-GM of the Red Sox. And what better way for Cherington to stick it to the Red Sox, if he’s so inclined, then by helping out their division rival.

So if Cherington wants a soft seat for a year or two as he re-evaluates his desire to be a GM, it makes all the sense for the Pirates to scoop up a good “free agent” before the offseason even starts. In an era where every advantage counts, why wouldn’t a team like the Pirates try to corner as much brainpower as possible, especially considering that the financial outlay would be less than the salary of a rookie making the league minimum.