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Pirates GM Neal Huntington still losing sleep over Jason Bay trade to Red Sox

11.14.11 at 12:40 pm ET

This is the life of a GM.

It has been more than three years since the Red Sox, Pirates and Dodgers enacted a head-spinning three-way trade at the 2008 deadline that sent Manny Ramirez from the Sox to Los Angeles, Jason Bay from Pittsburgh to Boston and four prospects to the Pirates. And yet, it is a deal that continues to haunt one of the principals involved in reaching it.

Pirates GM Neal Huntington, in a baseball roundtable discussion with Yankees GM Brian Cashman, Cubs president of baseball operations Theo Epstein and Red Sox scout Galen Carr in Randolph, Vt., was asked to describe what it was and is like to negotiate with Epstein, who orchestrated the Bay deal as the GM of the Sox. Huntington responded with gallows humor.

‘€œWith Theo, he always knew the players we gave up, we weren’€™t going to get a lot for, so he wasn’€™t willing to give up very much, so that’€™s probably why we never finished a deal unless we were taking your money,’€ Huntington joked.

‘€œJason Bay?’€ said Epstein.

‘€œYeah, you orchestrated the Jason Bay trade, which I’€™ve really tried to block out of my memory,’€ said Huntington. ‘€œI really had forgotten that one, or tried to. Now I’€™m done for the night. Thanks.’€

It was meant as a joke in passing, but on multiple occasions, Huntington referred back to that deal — a wild success for both the Dodgers and Red Sox (both of whom advanced to the League Championship Series in 2008) and a failure for the Pirates. The Pirates had arguably the most valuable commodity in the deal, a power-hitting outfielder in his prime who was performing at his All-Star peak. He was under team control not just for the 2008 season but also the following one at a contract that made him a bargain.

The Pirates were not going to be competitive in Bay’s remaining tenure in Pittsburgh, and so they dealt him on the assumption that the return would be greatest at a time when he could impact two championship seasons. The Pirates thought that the deal could impact them for years to come, as they acquired outfielder Brandon Moss and reliever Craig Hansen from the Sox and third baseman Andy LaRoche and Single-A starting pitching prospect Bryan Morris in the deal.

“We thought we were getting a guy with a chance to be an everyday right fielder (Moss). We thought we were getting a guy who had a chance to be a back-end bullpen guy (Hansen), a guy who had a very good chance to be a quality major league third baseman (LaRoche) and a starting pitcher (Morris),” said Huntington. “And right now, it looks like we’€™ve got a chance to have a reliever out of that trade.”

At another interval, when the GMs were discussing their worst trades, Huntington required neither time nor the actual names involved to make clear his sentiments about the Bay deal.

‘€œI think my answer is pretty obvious, unfortunately,’€ said Huntington.

Moss signed a minor league deal with the Phillies after the 2010 season. Hansen pitched just 17 professional games over the 2009 and 2010 seasons before being released by the Pirates at the end of spring training this year. The Pirates non-tendered LaRoche after the 2010 season and let him sign with the A’s.

Morris, now 24, is the lone player from the deal who remains in the Pittsburgh organization. He was converted to the bullpen in Double-A this year.

Even at a time when the Pirates have started to show promise (they were in first place as late as mid-July in 2011 before finishing the year in a 21-46 swoon), and when it appears their organization has started to develop the prospect base that could serve as the foundation of a contender, Huntington acknowledges that he is haunted by the missed opportunity to accelerate that process three years ago.

“It is one that I do lose sleep over, because I try to analyze the process time and again,” acknowledged Huntington. “We also need to understand how we were successful, whether it’€™s an amateur free agent drafting or a scout who saw something that no one else did. Where did you overvalue? Where did you undervalue? Truth be told, most trades are continual works in progress and it takes five to seven years to really accurately evaluate whether the trade that was made helped you.”

Unfortunately for Huntington, it has taken only half that time to get a gauge on the Bay deal, and to recognize it as a missed opportunity. There have been other successful deals — Huntington mentioned a trade with the Yankees from that same 2008 summer that netted a key starter (Jeff Karstens), reliever (Daniel McCutchen) and outfielder (Jose Tabata) — but for a GM of a team trying to build, it is clear that memories of failed deals do not fade easily are not eradicated by those that were successful.

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