24 Dec 2000: Quarterback Ryan Leaf #16 of the San Diego Chargers passes the ball during the game against the Pittsburgh Steelers at Qualcomm Stadium in San Diego, California. The Steelers defeated the Chargers 34-21.Mandatory Credit: Stephen Dunn /Allsport

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Letter Reveals Hunter S. Thompson Pressed Colts to Draft Bust Ryan Leaf Over Peyton Manning

Leaf found the letter Thompson wrote to Colts owner Jim Irsay in 1998 before the NFL Draft.

Hunter S. Thompson knew a lot about evaluating the quality of uppers, downers, screamers, and laughers, but he didn’t apparently didn’t know much about evaluating NFL quarterbacks.

Prior to the NFL Draft in 1998, the Fear and Loathing in Las Vegas author penned a letter to Indianapolis Colts owner Jim Irsay regarding his upcoming selection. Picking at No. 1 overall, the Colts were thought to be deciding between quarterbacks Ryan Leaf or Peyton Manning.

Thompson, a friend of Irsay’s as well as a football fan, wrote a letter encouraging his pal to go with Leaf instead of Manning because he thought he was better equipped to make it in the NFL.

“Dear James,” Thompson wrote. “In response to yr. addled request for a quick $30M loan to secure the services of the Manning kid – I have to say No, at this time. But the Leaf boy is another matter. He looks strong & Manning doesn’t – or at least not strong enough to handle that ‘Welcome to the NFL’ business for two years without a world-class offensive line. How are you fixed at left OT for the next few years, James? Think about it. You don’t want a china doll back there when that freak Sapp comes crashing in.”

Manning, of course, went on to win multiple Super Bowls and has a number of all-time passing records.

Leaf, who posted the letter on Instagram, is regarded as one of the worst busts in NFL history.

At least he has a sense of humor about it.

Read the full story at ESPN