Matt Harrington, Colorado Rockies, San Diego Padres, Tampa Bay Devil Rays, Cincinnati Reds
Harrington could be the worst holdout in professional sports history. Not only did the No. 7 pick turn down an offer of US$4.9-million from the Colorado Rockies in 2000, he then enlisted the help of Boras, who rejected a $1.2-million signing bonus from the Padres when the star pitcher was re-drafted as the 58th pick in 2001.
As Harrington's value continued to diminish, he entered his third draft, only to be taken in the 13th round by the Devil Rays as the 374th pick. He rejected Tampa Bay's offer of $5,000-$20,000 — standard contracts for players picked in the 13th round. He went back to try his hand at a fourth draft in 2003 and was picked up by the Reds in the 24th round. As the 711th pick, Cincinatti really owed him nothing but a chance to play.
Of course, this was not good enough so he returned for a fifth draft where he was picked 1,089th by the Yankees in the 36th round. Surprisingly, he was not offered a contract by the team.
Did he get the hint? Apparently not, as he was later passed over in the 2005 draft and became a free agent. Harrington attempted to land a spot in 2007 on a Cubs minor league team but was released shortly after.
According to ESPN, he now works for Costco and makes $11.50 per hour in the tire department.