Freddy Sanchez for Jeff Suppan – 2003
Freddy Sanchez was once one of the top infield prospects in the Red Sox system, but with Nomar Garciaparra locked in at shortstop the team felt that Sanchez was expendable. They needed to add an arm to their rotation, so they sent Sanchez and reliever Mike Gonzalez to the Pittsburgh Pirates for a package headlined by Jeff Suppan.
Suppan was originally drafted by the Red Sox, but management must have forgotten the 5.99 ERA he produced during his first three years in Boston. Or the four years after that where the results weren’t much better pitching for the Kansas City Royals. All they looked at was that current season, where a move to the National League improved his fortunes to the tune of a 3.57 ERA through 21 starts.
Prior to that, Suppan had been nothing more than a back of the rotation innings-eater. He did have five straight seasons in which he pitched 200+ innings. They just weren’t good innings.
Boston clearly thought that the then-28-year old had turned a corner, but they were quickly proven wrong. Suppan posted a 5.57 ERA in 11 appearances (10 starts) for the Red Sox to finish the season before quickly scampering back to the NL the following year.
Meanwhile, Sanchez would become a three-time All-Star for the Pirates and won a batting title in 2007. The Red Sox ended up trading Nomar a year later and spun through a seemingly endless cycle of shortstops that lasted until Xander Bogaerts put an end to the revolving door at the position.