Hunter S. Thompson grew up in Louisville, Kentucky, where the city’s most privileged youth were members of a boozy literary club called the Athenaeum. Thompson did not come from an affluent family, so he planned his entry into this society carefully.

With a few friends, he started an athletic club called the Hawks AC and organised various events around the city, which earned him an invitation to Castlewood, a feeder group for the Athenaeum. “Hunter was the first one of our immediate age group to get into Castlewood,” one of his friends later recalled.

This clipping, which I stumbled upon yesterday when researching a forthcoming essay, shows a 14-year-old Thompson promoting Castlewood in a local newspaper. Interestingly, he seems to have his own basketball team. Thompson was mostly a baseball player and later became known for writing about football.

His work proved successful and he was invited to join the Athenaeum. It was the Athenaeum’s journal, The Spectator, that published an often-quoted short essay he wrote. The final line appears often on social media:

who is the happier man, he who has braved the storm of life and lived or he who has stayed securely on shore and merely existed?

Neither his sports career nor his literary career took off at this point. For one thing, one of his legs grew markedly longer than the other, giving him his trademark walk but making sports difficult. For another, he was thrown in jail and kicked out of the Athenaeum (as well as missing his high-school graduation).

Thompson ended up joining the Air Force and worked as a sports editor at Eglin AF Base in Florida, and then blagged his way into various later roles until he had developed enough talent as a writer to make his name.

Although he became famous for writing about motorcycle gangs, drugs, and politics, he started and ended his writing career covering sports.

You can read about Thompson’s teenage crime spree in my recent essay:  huntersthompson.substac… His brief athletic career and efforts at entering Louisville’s high society are well covered in William McKeen’s excellent biography, Outlaw Journalist, chapter 1. It’s also detailed to some degree in my book, High White Notes: The Rise and Fall of Gonzo Journalism.