In this era of citizen journalism and social media and “fake news” I can’t help but wonder what Hunter S. Thompson might have had to say.

What if Hunter S. Thompson had spent 2016 riding on Donald J. Trump’s campaign bus? What if he spent 2017 wandering the woods with Hilary? What if he’d been along for the ride in Helsinki? Roaming the halls of the Internet Research Agency in St. Petersburg?

I can only imagine what he might have had to say, and the magical way he would have said it.

Thompson, one of Louisville’s most famous sons, pioneered a literary genre known as “gonzo journalism.” The bold style tossed out traditional journalistic detachment and discipline in favor of immersive, first person narrative that crackled with sarcasm and played fast and loose with definitive facts.

There’s no small amount of irony in the fact that in the midst of the personal narrative and hyperbole and shenanigans there’s an element of truth. Thompson’s style stood in sharp contrast to the carefully constructed, balanced, thorough stories of fellow journalists, who took great pains not to “become the story.” Thompson gleefully cast himself as the central character, then gave the reader full access to his every inner thought and opinion. The result was an authentic, countercultural voice that resonated with an entire generation.

It takes moxie to define a whole new perspective, and Thompson had it. Here’s how:

Moxie shows up early.

Thompson was born and raised in Louisville, the oldest of the three sons of Jack and Virginia Thompson. The family lived in the Cherokee Triangle, and young Hunter made his way through Bloom Elementary, Highlands Middle School, Atherton High School and eventually Male High School. (Ironically, as a native Lousivillian, I attended all of these institutions of “higher learning”-except for Male High School). His school career was marked by an early interest in athletics, recognition of his literary prowess and social status, and a serious brush with the law.

Thompson was charged as an accessory to robbery, an incident which landed him in jail for 31 days and cost him his opportunity to graduate from Male and his membership in the Athenaeum Literary Association, a school-sponsored literary and social club populated by elite, upper class Louisvillians.

After his sentence was up, Thompson enlisted in the Air Force and headed off to basic training. While in the military, he began attending college and writing about sports for local newspapers on the sly, as military members were forbidden from having side gigs. It didn’t take long for the Air Force to recognize that Thompson was not a good fit. He was talented, but he had a bad attitude and wouldn’t follow the rules, and his rebellious nature seemed to influence others to do the same.

Given that, can we even be surprised about the trajectory of his career?

People with moxie aren’t always appreciated.

Thompson’s early career was marked by more dismissals. He was fired from his position at Time magazine for insubordination. He was fired by The Middletown Daily Record for damaging property and arguing with an advertiser. He made his way to the Caribbean to work as a sports reporter in Puerto Rico but the publication folded, and he had a hard time finding steady work after. He submitted dozens of stories to various publications, most of which were rejected.

The period of his life was far from productive, however. He wrote two novels, one of which, The Rum Diaries, found its way to publication.

In the late 60s and 70s after a decade grinding away writing for various publications, he began to break through and do his most notable work. In 1967 he published his book Hell’s Angels, written after he spent a year immersed in motorcycle gang life. In 1970 he returned to his Louisville roots and wrote a magazine feature entitled The Kentucky Derby is Decadent and Depraved which cemented his reputation as a leading counter cultural voice. He wrote a series for Rolling Stone magazine that became his celebrate book Fear and Loathing in Las Vegas, published in 1971.

It was hard to find a great fit for his talent, but was unrelenting in honing his craft and refining his voice.

Moxie has a dark side, too.

Despite his many notable works, Thompson didn’t always deliver. His literary career is littered with blown deadlines and unfinished work.

Perhaps he was undone by his own rebellious nature, his rise to fame, or his prodigious and well chronicled consumption of drugs and alcohol.

In the end, his life had an unfinished feel, too. At the age of 67, he committed suicide after a string of health problems brought on by aging and hard living left him frustrated and depressed. His suicide note reveals much:

“No More Games. No More Bombs. No More Walking. No More Fun. No More Swimming. 67. That is 17 years past 50. 17 more than I needed or wanted. Boring. I am always bitchy. No Fun — for anybody. 67. You are getting Greedy. Act your (old) age. Relax — This won’t hurt.”

He was wrong, of course, it did hurt. The loss of Thompson hurt those who loved him most, and hurt the culture shaped by his revolutionary style.

If you had the chance to ask Thompson anything, what would you ask?

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