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Come Fan with UsWednesday, June 24, 2026

Hunter S. Thompson told Colts owner Jim Irsay to draft Ryan Leaf over Peyton Manning

Bad at NFL scouting. Great at drugs, though.

Ryan Leaf and Ryan Leaf
Ryan Leaf and Ryan Leaf

Legendary writer Hunter S. Thompson loved many things. Drugs. Renaissance fairs. Chivas Regal. Culture-creating journalism. Dove Bars. Several other kinds of drugs.

And also former San Diego Chargers quarterback Ryan Leaf. Way more, in fact, than he liked Leaf’s 1998 draft-mate Peyton Manning.

Leaf unveiled a 1998 letter from Thompson to Indianapolis Colts owner Jim Irsay Thursday, detailing the counterculture writer’s preference of the Washington State quarterback over the more polished Manning with the No. 1 overall pick in that year’s draft. By Thompson’s account, Leaf was the stronger prospect of the two, and more likely to survive behind Indianapolis’s porous offensive line as a rookie:

Dear James,

In response to yr addled request for a quick $30M loan to secure the services of the Manning kid — I have to say No, (sic) 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 (sic) doll back there when that freak [Warren] Sapp comes crashing in.

Okay. Let me know if you need some money for Leaf. I expect to be very rich when this [Johnny] depp (sic) movie comes out.

Yr. faithful consultant,

HUNTER

Thompson’s love of sports was an overarching theme that ran through his writing career. He covered the Eglin Air Force Base’s football teams while serving in the military and began his journalism career as the sports editor of a small Pennsylvania newspaper. He bookended that service as a columnist for ESPN.com’s now-defunct Page 2, a position he held from 2000 until his death in 2005.

But while Thompson had a well-researched background in the field, his preference of Leaf over Manning would be one of his least successful reports. Manning became the greatest player in Colts history, leading the team to its only Super Bowl win after the 2006 season and earning league MVP honors an astonishing five times. Leaf, conversely, won four NFL games as a starter and was out of the league by 2002.

The bigger question is when Thompson found time in his busy schedule to break out his typewriter and fire off a letter to Irsay:

Probably sometime around 4:54 and 5:05 p.m., in between the “cocaine” and the “cocaine.”

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