#7 Tony Armas Jr, 1 year $3.5 million
The Pittsburgh Pirates pitching staff was rather bleak during the Dave Littlefield era. Littlefield could not draft a pitcher if he had to. He passed on the likes of Clayton Kershaw and Zach Greinke in drafts. He also missed by taking pitchers like Brad Lincoln and Daniel Moskos with top selections and them not working out at all.
So when the Pittsburgh Pirates brought in veteran pitcher Tony Armas Jr there was some hope that he would be an upgrade to the team's rotation. In 2007, the Bucs signed him to a 1-year deal with a club option for 2008, which like many of the others on this list would be declined. Armas Jr was a complete bust for the Pittsburgh Pirates.
Armas Jr. signed a one-year, $3.5 million contract with the Pirates on February 1, 2007, with a mutual option for 2008. He was expected to bolster the Pirates' starting rotation, but he struggled from the beginning of the season. In his first three starts, he went 0-3 with an ERA of 8.92.
As a result of his struggles, Armas Jr. was removed from the rotation in late April 2007 and moved to the bullpen. He made six relief appearances before being placed on the disabled list in early May with a strained right forearm. Armas Jr. returned to the Pirates in June 2007 but continued to struggle in both the rotation and bullpen. He finished the season with a record of 4-5 and an ERA of 6.03 in 31 games (15 starts).
The Pirates declined their club option on Armas Jr. for the 2008 season. This essentially ended his career with the Pittsburgh Pirates making him a free agent. He eventually signed with the Boston Red Sox for the 2008 season, where he made six appearances (two starts) before being released in July. Another veteran pitcher brought in who was paid a chunk of money to not produce or be a trade piece.