Top Five worst trades in Pittsburgh Pirates history

Jul 17, 2015; Phoenix, AZ, USA; San Francisco Giants starting pitcher Ryan Vogelsong (32) throws during the twelfth inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Matt Kartozian-USA TODAY Sports

1. July 30, 2001: Jason Schmidt and John Vander Wal traded to the San Francisco Giants for Armando Rios and Ryan Vogelsong.

This could be a case of selling low out of desperation on a player a bit too early, but Jason Schmidt went from a slightly above league average pitcher with the Pirates to a two-time Cy Young finalist with the Giants. With the Pirates, Jason Schmidt compiled a record of 44-47 with a 4.39ERA, a 4.29FIP, an ERA+ of 102 and was worth 10.8WAR, but after the trade Schmidt transformed into one of the league’s great pitchers. With the Giants, he went 78-37 with a 3.36ERA, a 3.26FIP, an ERA+ of 126 and was worth 22.6WAR.

John Vander Wal was already an established big league player when he got to the Pirates in 2000. For his career he was a very average offensive player. Slashing .261/.353/.442/.795/104OPS+, but in his parts of two seasons with the Pirates, he actually saw a huge increase in his numbers. Putting up a very respectable .290/.389/.522/.911/129OPS+. He was also worth 2.9WAR in his time with the Pirates vs. 3.5WAR for the rest of his 14 year career. While trading him didn’t hurt nearly as much as trading Schmidt, it was still losing a very a solid offensive contributor for very little return.

Ryan Vogelsong was a monumental bust for the Pirates after the trade. In his 5 seasons in Pittsburgh he put together a record of 10-19 with an ERA of 6.00, a FIP of 4.88, an ERA+ of 72 and was worth -2.1WAR. The worst part of Vogelsong being included in the deal was he wasn’t even a top prospect in the Giants system and was coming off a 2000 season in Double-A where he went 6-10 with a 4.23ERA and a WHIP of 1.429.

Armando Rios was injured during the time of the trade because Dave Littlefield apparently didn’t believe in physicals. When he was healthy with the Pirates he was pathetically below average on both offense and defense. During his parts of two seasons with the Pirates, his numbers were not particularly impressive as he slashed .265/.323/.332/.655/72OPS+ and was worth -0.6WAR. Couple Rios’ and Vogelsong’s numbers with how successful Schmidt was with the Giants, then you have all the makings of one of the worst trades in Pirates history.

Dave Littlefield made many poor trades involving pitchers, but number four on our list might be the most mind numbingly annoying…

Next: Number 4