Hunter S. Thompson predicted, in the most general sense, the coming of Donald Trump, or at least the flourishing of the reactionary, retaliatory, mutually-assured-destructive base that put him and his ilk into power. (He also noted, as early as anyone, that the American experiment had peaked and perhaps failed.) But, seer or meerly perceptive, Thompson was no match for the vagaries of NFL talent evaluation; he was just as much an idiot as the rest of us.
Thompson was (unexpectedly and yet entirely logically) a friend of Colts owner Jim Irsay, and a month before the 1998 draft, Thompson weighed in on the burning question of the time: Peyton Manning or Ryan Leaf? In a letter to Irsay, copied to both ESPN head John Walsh and Johnny Depp, Thompson advised Irsay that Leaf was the safer draft pick because “he looks strong & Manning doesn’t.”
Thompson was wrong about Leaf and wrong about getting very rich from “this [D]epp movie”—Fear And Loathing In Las Vegas was a commercial failure.
Two years after the letter, Thompson would begin his column for ESPN’s Page 2, which he wrote up until his death by suicide in 2005. (His suicide note was titled “Football Season Is Over.”) In 2001, Thompson advised Irsay to purchase the original 119-foot scroll on which Jack Kerouc wrote On The Road, for which Irsay paid $2.4 million, then a record for a manuscript.
Leaf, of course, would become an all-time draft bust and descend into a morass of legal problems and substance abuse. But he’s been out of prison since 2014, apparently sober, and he now hosts a Pac-12 satellite radio show.