Hunter S. Thompson Told Jim Irsay to Draft Ryan Leaf over Peyton Manning in 1998

Hunter S. Thompson is a legendary writer and pioneered his own form of journalism. When it came to NFL talent assessment, Thompson was decidedly less legendary.

Former San Diego Chargers quarterback Ryan Leaf shared a letter from Thompson to Indianapolis Colts owner Jim Irsay. Thompson informed Irsay he wouldn't provide a $30 million loan if the Colts were to select Peyton Manning but would do so if the team committed to taking Leaf first overall in the 1998 draft:

The Colts' decision to not take Leaf is one of the more interesting "what ifs" in NFL draft history. At the time, placing Manning over Leaf was far from a universal opinion. But Leaf's and Manning's careers went in significantly divergent directions following draft day.

Colts fans will be thankful Irsay and Indianapolis' front office stuck to their guns and picked Manning, who went on to be one of the greatest quarterbacks in NFL history.