Ryan Leaf
Ryan Leaf.

Chargers quarterback Ryan Leaf prepares to throw a pass against the Pittsburgh Steelers in December 2000.

Stephen Dunn/Getty Images

Like Ricky Williams, Ryan Leaf was one of the top college prospects in the U.S. when the San Diego Chargers traded three draft picks and a four-time Pro Bowl player to the Arizona Cardinals for the right to grab the young quarterback in the 1998 draft [source: Spratt]. In a flash of fortuitous brilliance, the Indianapolis Colts passed on Leaf to draft another highly touted quarterback, Peyton Manning.

Leaf signed a four-year, $31.25 million contract with the Chargers, including a guaranteed $11.25 million signing bonus -- the largest ever paid to a rookie at the time. Blame it on the big-money pressure, but the poor quarterback's career was doomed from the start. A shoulder injury kept him sidelined for a whole season and when he was back in the game, he only managed a 4-17 record as a starter. An eventual trade to the Dallas Cowboys was the beginning of the end.

The former multimillion-dollar draft selection went on to work as an assistant golf coach at West Texas A&M before being convicted of eight felony counts of illegal prescription drug possession and getting canned [source: Johns]. In December 2010, Leaf received yet another contract, to write three books about winning, losing, addiction -- and what it feels like to be one of the biggest busts in NFL history [source: Spratt].