3. Chris Carter and Eddie Lora for Billy Wagner (2009)
The level of complexity involved in this deal pales in comparison to number four on the list. That this deal only involved two teams and three players is fortunate considering how late it is while I'm writing this. If this was another three team monster deal I might just end up writing about how great the recent McKendry trade was. Or Epstein's little known trade of Kevin Cash for a sandwich.
The genius in the trade for Billy Wagner came in getting value while giving up what the Red Sox have in abundance, organizational soldiers and financial relief. At the time this trade was made the Red Sox had a 1.5 lead in the Wild Card and were six games behind the Yankees. Wagner was just coming back from Tommy John Surgery and the Mets were languishing 16.5 games back in the NL East. Wagner's four year, $43 million contract was expiring at the end of the season and the Mets, going nowhere as usual, were looking to save the eight and a half cents they'd recoup by dumping him.
That's the background, but the hidden brilliance of this deal was that not only did the Sox pick up a boarder-line left handed Hall of Fame reliever for the stretch run and the playoffs, but they got two first round draft picks as well. Because the Braves draft pick was not protected, the Red Sox received the 20th pick in the 2010 draft and another pick in the compensatory round, pick number 39 for the loss of Wagner. The Sox selected Kolbrin Vitek and Anthony Ranaudo, respectively, with those picks.
By offering arbitration to Wagner, something the Sox knew he wouldn't accept because the closer job was occupied in Boston, the Red Sox got three somethings (Wagner and two picks) for two organizational players who have done nothing for the Mets. In baseball talent doesn't get much more free than that.
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Tomorrow: We're getting close. Trade Number Two on the list...