Sobering Truths in The Rum Diary

Hunter S. Thompson is one of those writers who everyone seems to have read a hundred times over. I’ve had a number of phases in my life when the crazed king of Gonzo journalism has reigned over my bookshelf. However, while his most popular works are certainly worth picking up, it is one of his lesser-known books that has been on my mind ever since I first read it when I was sixteen. That book was The Rum Diary. 

Set on the sun-soaked shores of Puerto Rico, Hunter S. Thompson’s The Rum Diary is a curious novel that offers an unparalleled insight into the misanthropic mind of one of America’s most well-loved countercultural writers.

Thompson’s early years writing in Puerto Rico.

Written in the 1960s, during Thompson’s early 20s, the writer dreamt that his first literary excursion would become a contender for the canon of “Great American Novels”. However, his first work instead went down a different pathway of literary clichés – it became his long-lost novel.

With Thompson eventually finding his fame with books such as Hell’s Angels and Fear & Loathing in Las Vegas, his little Puerto Rico novel was put on ice until 1998 when it was picked up by Simon & Schuster in the US and Bloomsbury in the UK.

The events of the novel take place during the early 1950s, a few years after the US decided to make Puerto Rico an unincorporated dependent territory. This historic context injects the novel with a volatile political backdrop where cultures clash and crooked business booms.

Thompson’s boozy protagonist, Paul Kemp, is a “vagrant journalist” who has roamed all around the world in search of work. In Puerto Rico, Kemp finds a twisted idyll that offers fortunes and riches in exchange for one’s own morals.

Kemp characterises a certain state of shaky masculinity. He is a self-proclaimed “suckfish” – a slack, easy-going bottom feeder who is happy to benefit off the greed of others. A lustful cynic, Kemp is ultimately petrified of ageing, something shared with almost all of his colleagues.

Working at the San Juan Daily News – an English language newspaper in Puerto Rico’s capital – Kemp is introduced to an array of eccentric “winehead” creatives who are thought to be looking for an easy ride. With a lazy workforce and a poor turnover, The Daily News is far from a stable venture, but the whole operation is tied together by Managing Editor, Lotterman, an ex-communist on the warpath to expel all “wineheads” and “perverts”.

Following Kemp’s arrival on the island, the novel essentially documents his drunken exploits, lustful misadventures and the downfall of some of his closest associates. Yet, beneath the rum-soaked surface of Thompson’s work, there are a few sobering truths to be gleaned.

Putting Puerto Rico Under the Microscope

Like any skilled novelist, Thompson’s use of setting is layered and well-researched. An island of tropical rainforests, 16th century fortresses and a number of glorious Caribbean beaches, Thompson is quick to analyse Puerto Rico’s curious cultural backdrop.

Designed & illustrated by Roman Stevens

The island’s unincorporated status means it is both closely bonded to the US and also kept at arm’s reach. Puerto Ricans are US citizens and are permitted freedom of movement but cannot vote in the US Congress, due to the island not being a formal state. The same sense of kinship and distance can also be applied to Puerto Rico’s status as part of the West Indies. Spanish and English are both spoken in Puerto Rico and there are a huge number of different ethnic groups.

With all of that in mind, where better to write a novel featuring a medley of ignorant American expats?

Thompson primarily explores America’s relationship with Puerto Rico. Often seen as an island brimming with “potential”, Thompson creates characters who are almost unable to see the country as anything other than a blueprint for an array of glittering shorefront hotels.

Kemp is quickly introduced to Hal Sanderson, an influential businessman who is essentially a walking embodiment of American capitalism. Sanderson enrols Kemp’s help in his plan to turn the neighbouring island of Vieques into the Caribbean’s next biggest tourist resort. Employed to write up the plans for the resort, Kemp notes, “I was being paid twenty-five dollars a day to ruin the only place I’d seen in ten years where I’d felt a sense of peace.” Kemp’s Caribbean escapades often resemble something of a morality check for the character.

Thompson, writing in front of a new hotel development.

Regarding those who work at the Daily News, Puerto Rico becomes something of a last chance saloon for downtrodden yanks. Yet, it’s also a no-chance saloon for the locals. The height of ignorance comes when the journalists are trying to figure out why Puerto Ricans are leaving for the US mainland. Thompson’s expats are unable to understand that there’s not a lot of locals who are able to benefit from American development projects.

The Island Bites Back

It’s fair to say that Thompson’s expat characters maintain a certain sense of disrespect for the island and its inhabitants. Surprisingly perhaps, Thompson doesn’t always let them get away with this. On more than one occasion, the novel exhibits a level of intensity and terror that make the story feel a lot more like a Paul Bowles novel.

After a drunken escapade in which Kemp and his colleagues, Yeamon and Sala, incur the wrath of a local bartender, the three become involved in a violent episode with a number of Puerto Ricans. They are subsequently incarcerated for a night and beaten by police. During sentencing, however, they are saved by Sanderson – an action which speaks volumes for the influence of the Yankee dollar.

This episode is much more akin to the events portrayed in Thompson’s later work. A gun-toting advocate of almost every drug under the sun, Thompson was well-loved for his questionable antics. The video below, “An Evening at Owl Farm” is evidence enough of that:

At a later moment in the novel, at the carnival in St Thomas, Yeamon’s girlfriend is abducted by locals after she and another man are seen raunchily dancing. While she eventually makes her way back to Puerto Rico, this episode and the one before are evidence of Thompson’s portentous worldview – this is not a playground for giddy American expats.

Sounds of a San Juan Night

The novel’s fatal conclusion is Thompson’s final message that no-one can escape decline and degradation, and everyone is capable of consuming too much rum.

I believe that Thompson’s early novel is ultimately a jaded masterpiece. A Hemingwayesque attempt at the “Great American Novel”, Thompson instead achieves something far more akin to his own literary flair and skillset.

The book concludes with one of my all-time favourite passages of fiction:

“Voices rose and fell in the house next door and the raucous sound of a jukebox came from a bar down the street. Sounds of a San Juan night, drifting across the city through layers of humid air; sounds of life and movement, people getting ready and people giving up, the sound of hope and the sound of hanging on, and behind them all, the quiet, deadly ticking of a thousand hungry clocks, the lonely sound of time passing in the long Caribbean night.”

For more information about Hunter S. Thompson, The Rum Diary and its 2011 film adaption of the same name, check out this brilliant documentary. Go for the details and stay for the flute (of which there is far too much…)