Why trading Jason Bay didn't work out like the Pirates had hoped

BRADENTON, Fla. – Ordinarily, deals that involve the movement of superstars in exchange for prospects require years to analyze. Yet just 20 months after the Red Sox altered their dynamic at the 2008 trade deadline by acquiring Jason Bay and shipping away Manny Ramirez (and his remaining 2008 salary) and a pair of prospects, a near-final evaluation of the deal from Boston’s perspective is already possible. 

That is because the book is likely closing – or at least entering a new chapter – on the two prospects whom the Sox included in the deal. The two minor leaguers whom the Sox sent to the Pirates as part of that deal have seen their careers head south with Pittsburgh.

For the Pirates – who retain the four prospects acquired in the deal – and the Dodgers – who still have Ramirez – the evaluation is somewhat more open ended. But for the Sox, the muted impact of the two minor leaguers they shipped to Pittsburgh, combined with the fact that Bay has now moved on in free agency, has made it possible to get a read on the total impact of the deal on Boston. 

“Obviously, it worked out great for Jason and great for Boston,” Pittsburgh GM Neal Huntington reflected on Friday, after watching the Pirates beat the Red Sox, 9-7, in an exhibition game. “It’s still a work in progress for us.”

Indeed, with the benefit of hindsight, Huntington suggests that the Pirates now believe that they had a better deal on the table for Bay than the one that they ultimately swung. He also recognizes that his team might have received a greater haul than the four players (Brandon Moss and Craig Hansen from the Sox; Bryan Morris and Andy LaRoche from the Dodgers) whom it acquired had it waited until the offseason to deal Bay.

Clearly, had the Pirates elected either of those alternatives, it could have altered the shape of four or more franchises (Sox, Pirates, Dodgers, and whatever other team(s) involved in a deal for Bay). But hindsight is an imperfect science, and the “what if” game is an endless one. 

“Until 10 minutes before the deadline, we’d made the decision to hold [Bay],” said Huntington. “I think if the rest of the industry had been able to predict that he was going to go do what he did in Boston, we’d have gotten a lot more for him. 

“[But] at the time, we felt like we were getting a guy with a chance to be an everyday third baseman; a guy with a chance to be an everyday right fielder; a young, upside starting pitcher prospect; and a [guy with a] chance to be a closer. We felt pretty good about the return at that point. …

“As we look at other deals on the table, there was probably one other deal that we looked back on that in hindsight would have been a better deal. For the same information we had at that point in time, yes, we want a better return. But hindsight evaluations aren’t always fair. If we look at all the information we had, we still don’t feel like we missed anything big.”

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The Pirates will need years to determine the final shape of their haul. On the other hand, there are several parts of the deal on which a final assessment is already possible. 

THE STARS: BAY VS. MANNY

The Sox gave up Ramirez, money (the remained of Ramirez’ ’08 salary) and prospects Brandon Moss and Craig Hansen in order to import Bay. 

Had the deal not been made, according to a team source, the Red Sox remained unsure of how they would proceed with the mercurial Ramirez. It was unknown whether bridges could possibly be rebuilt following his campaign to force an exit. The team hadn’t decided whether it would be worth exercising the $20 million option for the 2009 season. Had the team declined to do so because of a preference to part ways, it was likely but slightly short of certain whether it might offer him arbitration and roll the dice that he wouldn’t accept so that it could get a pair of draft picks. 

Ramirez represented uncertainty. He might or might not quit on the