1. Josh Hamilton: Five Years, $125 million, 2012
One season after signing Pujols, the Angels signed Josh Hamilton to a five-year deal. The years and money weren't as extreme, but it was an absolute disaster.
Hamilton won the MVP award for the Rangers in 2010. He then helped lead the Rangers to an AL Pennant in 2011, and finished top-five in the MVP voting in 2012. He was without a doubt one of the best players of baseball. Of course, immediately after the Angels signed him, things went south.
Hamilton's first season with the Angels wasn't anything close to what they were expecting. He slashed .250/.307/.432 with 21 home runs and 79 RBI. He had a 108 OPS+ in 151 games. Not great, but at least he played.
The following season, Hamilton was limited to just 89 games. He slashed .263/.331/.414 with 10 home runs in those games in a season ruined by injuries.
Hamilton, who had a long history with drug addiction, suffered another relapse. The Angels then traded him back to Texas and took on most of the remaining money on his deal.
Hamilton played one full season on the Angels and wasn't anything more than a slightly above-average hitter. Injuries and the drug relapse ruined his time with the Angels.