Pick: 2nd overall
While he may not be winning at anything else, Ryan Leaf won the title of "Biggest NFL Draft Bust of All Time."
The San Diego Chargers had the second overall pick in the 1998 draft, right behind the Indianapolis Colts. After the Colts took a young Tennessee quarterback named Peyton Manning, the Chargers jumped at the opportunity to select Leaf, a QB from Washington State. Worst. Mistake. Ever.
Leaf only spent two years with the Chargers before being shipped off to the Dallas Cowboys for his final season. He only completed 48.4 percent of his passes and threw 14 touchdowns. He did, however, rack up 36 interceptions.
Leaf's problems on the field don't even compare to his problems off the field. The disgraced quarterback is currently in custody at the Cascade County Detention Center, where he faces two felony counts of burglary and two felony counts of of criminal possession of a dangerous drug.