James Loney 3yr/$21M (2014)
James Loney is the first player on this list where the contract did not work out in the Rays favor. After signing his extension, Loney hit .290 for the year and had 600 at bats for the first time in his career. That is really the only stat that stands out when it comes to James Loney. He was sidelined for almost half of the season in 2015 due to injuries only playing in 104 games. In 2016, Loney did not make the opening day roster and the Rays released him, eating the rest of the contract for 2016. Overall, Loney came to the Rays, secured a big pay day and left without providing much value.