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The story behind Hunter S. Thompson's insane letter pushing the Colts to draft Ryan Leaf over Peyton Manning

Opinions raged about Ryan Leaf and Peyton Manning at the 1998 NFL draft, but none put money in it like Hunter S. Thompson claimed to. (Getty Images)

Right now, Ryan Leaf is widely remembered as one of the biggest NFL draft busts in history, but part of that is the success of Peyton Manning, the quarterback Leaf competed with to become the No. 1 overall pick in the 1998 draft.

It sounds absurd to compare Leaf with the future Hall of Famer now, but it was once an actual debate, and we’ve now learned very few were on Leaf’s side like Hunter S. Thompson.

On Thursday, Leaf tweeted out a copy of the letter written by Thompson to Indianapolis Colts owner Jim Irsay in 1998, in which the writer of books like “Fear and Loathing in Las Vegas” and creator of the gonzo journalism movement tells Irsay in no uncertain terms that he should draft Leaf first overall.

Hunter S. Thompson’s letter to Jim Irsay


There is a lot going on in that letter, including:

  • Thompson claiming that Irsay asked for a $30 million loan to sign Manning and denying him.
  • Thompson saying he will give Irsay the money if Irsay drafts Leaf because Leaf looks “strong” and Manning does not.
  • Thompson openly wondering if the “freak” Warren Sapp was going to break the “china doll” Manning.
  • Thompson claiming he will be very rich thanks to the film rights of “Fear and Loathing in Las Vegas” starring Johnny Depp (which had a budget of $18.5 million and grossed $13.7 million).
  • Thompson cc’ing ESPN executive John Walsh, who is widely credited for turning SportsCenter into an insitution.

It’s a wonder of a letter, and here’s how it happened, as told by Leaf.

How Ryan Leaf received the Hunter S. Thompson letter

Leaf gave further details surrounding the letter and his reaction during an appearance on The Rich Eisen Show, including the story of how a copy of the letter ended up in his email inbox. It all began when Leaf, who has been working as an ambassador for a sober living community called Transcend, went to a Los Angeles Dodgers game.

“I’m a Chicago Cubs fan and they were in town last week, and I was sitting behind the dugout,” Leaf said.” A guy tapped me on the shoulder and said ‘Are you Ryan Leaf?’ I said ‘Yes, sir,’ and he said ‘Man, I’m such a fan of what you’re doing now with the foundation and everything like that.’ We talked for a little bit and he said ‘Have you ever seen the Hunter S. Thompson letter?'”

The man told Leaf he was a former neighbor of Irsay and said received the letter while working in DirectTV Japan, as you do. When asked if he would like to see the letter, Leaf answered an emphatic yes and was soon laughing about it with his fiancee.

“I showed it to my fiancee, who is a huge Hunter S. Thompson fan and we read it,” Leaf said. “The absurdity of the fact that a) Hunter S. Thompson knew who I was and b) that he was trying to convince Mr. Irsay to draft me instead was just comical. And not to see it for 20 years, it’s just nowhere to be found.”

How Hunter S. Thompson met Jim Irsay

Leaf and Eisen added that they confirmed the letter’s authenticity by calling Walsh. The former executive vice president of ESPN said the letter was indeed real and told his old colleague Eisen that Irsay became friendly with Walsh when he bought a first edition of “On the Road” by Jack Kerouac.

In order to authenticate the book, Irsay, naturally, reached out to Thompson, a big fan of both Kerouac and the NFL, to authenticate it. The two apparently hit it off from there, and that’s how Thompson came to write a letter pushing the Colts into what might have been one of the worst decisions in NFL history.

We all know how it worked out from there. Manning turned into a Hall of Fame quarterback for the Colts and began his career with an NFL-record 227 consecutive starts despite being a “china doll.” Leaf played three seasons in the NFL before washing out of the league. And Hunter S. Thompson, well, he just continued to be Hunter S. Thompson.

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