Josh Hamilton, Texas Rangers
Slugger Josh Hamilton has the dubious distinction of being one of the worst free agent signings in Major League Baseball history. That's because after four seasons with the Texas Rangers, the North Carolina native was paid a whopping $125 million in a five year deal by the Angels, only to almost immediately underperform and quickly find himself sidelined by both a shoulder injury and drug addiction. After a mere three seasons in sunny Anaheim, Hamilton was traded back to Texas. Later shipped off to the minors, the once-promising player was subsequently released by the Rangers earlier this year.