Curt Schilling and Brady Anderson
Every Red Sox fan knows that their trade for Curt Schilling prior to the 2004 season was one of the main moves that helped the team finally win the World Series, but what a lot of them may not know is that the Red Sox had Schilling before. He was drafted by the Red Sox in 1986 and spent two years in their minor league system before being traded to Baltimore.
Along with Schilling, the Red Sox traded another prospect of theirs, Brady Anderson. In return, the team got pitcher Mike Boddicker. Boddicker actually pitched pretty well in his two and half seasons in Boston, going 7-3 in 1988, 15-11 in 1989, and 17-8 in 1990. Along the way he helped the Red Sox win the AL East in 1988 and 1990 where they were swept in the ALCS both times by Oakland.
Schilling went on to find success in Philadelphia, leading them to the World Series in 1993 and then in Arizona where he teamed up with Randy Johnson to help the Diamondbacks win it all in 2001. Brady Anderson enjoyed a fourteen-year career in Baltimore, hitting 210 home runs along the way (including a 50 home run season in 1996).
This trade wasn’t necessarily terrible in the sense that who the Red Sox got in return didn’t pan out. Boddicker was solid and helped the team win during his time in Boston. However, the two prospects the Sox gave up were better than what they got back. Luckily, they got a do-over with Schilling which helped them win two World Series in 2004 and 2007.