This one came up a couple of times in the comments. It’s interesting because it’s an example of how, even when Dave Littlefield did something right, it wasn’t by design.
On July 22, 2003 — the day before they traded Aramis Ramirez — the Pirates traded lefties Scott Sauerbeck and Mike Gonzalez to Boston for right-handed relievers Brandon Lyon and Anastacio Martinez. Boston was in a pennant race and wanted a left-handed reliever, and Sauerbeck was an overrated lefty specialist who’d had one really good year in 2002.
Judged at the time, the trade was a poor one for the Pirates because of the inclusion of Gonzalez. He was a hard-throwing lefty, especially back then, when lefties throwing in the mid-90s were rare. He’d just made the conversion to relief in AA and was the most promising talent in the trade. Martinez also had just converted to relief in the minors and also threw hard, but wasn’t as promising as Gonzalez and didn’t have a good track record. Lyon was an undistinguished reliever, but the Pirates had just traded their closer, Mike Williams, the day before as part of the salary dumping necessitated by Kevin McClatchy’s mismanagement. The Red Sox had employed Lyon briefly as a closer and he’d gotten nine saves. I thought at the time that Littlefield, who was the living antithesis of “innovation,” was desperate to acquire a pitcher who had some major league saves on his resume.
Very soon after the trade, the Pirates claimed that Lyon had an injury that Boston had failed to disclose. The Red Sox vehemently denied it, but they also quickly un-did the deal. Lyon ultimately missed the 2004 season, so I think the Pirates’ claim was probably accurate. The unraveling of the trade took the form of a second trade. The Pirates sent Lyon and Martinez back to Boston, along with right-handed starter Jeff Suppan, and got Gonzalez back along with infield prospect Freddy Sanchez. Sauerbeck stayed in Boston.
The whole affair was a disaster for Boston. Suppan, who’d been pitching well for the Pirates, went 3-4, 5.57 for Boston. He signed with St. Louis as a free agent after the season and had three good years there, then had three below-average seasons for Milwaukee. Sauerbeck was awful in 26 games with the Red Sox, then was hurt all of 2004. He resurfaced later with Cleveland and Oakland, but didn’t do much. Martinez pitched just 11 times in the majors and did badly. The Sox sent Lyon to Arizona after the season as part of the deal for Curt Schilling. After missing 2004, Lyon had a number of good seasons pitching in relief for Arizona, Detroit, Houston and Toronto.
The Pirates did much better. Gonzalez had three strong, sometimes dominant seasons for them, eventually becoming their closer. His only real problem was Lloyd McClendon’s rapidly increasing paranoia about young players, as it took a long time before McClendon was willing to use Gonzalez in high-leverage situations. The Pirates ultimately traded Gonzalez to Atlanta for Adam LaRoche. Gonzalez was very erratic after that as he struggled with arm and control problems.
Sanchez ultimately became the Pirates’ starting third baseman, gaining a regular job after fierce resistance from Jim Tracy* and then only because Joe Randa got hurt. He won a batting title in 2006, moved to second, and made three All-Star teams. He was prone to nagging injuries, though, and tended to play extremely badly when he wasn’t 100% healthy. The Pirates traded him to San Francisco in 2009 and he mostly played well for the Giants, but often wasn’t healthy. Due to the injuries, his career ended in 2011 at age 33.
*While Randa was out, Sanchez battled for the league lead in batting. Tracy belittled what Sanchez was doing, claiming that it was only because Tracy was choosing Sanchez’ spots. Tracy was a horrible manager.