I had the misfortune of being nourished by the visions and
dreams of great Americans—the poets and seers.
Some other breed of man has won out.
—Henry Miller, 1945
They had met in a bar on Christopher Street in the Village in 1958. Sandra Dawn Conklin was in the city, visiting her Goucher College roommate, Eleanor McGarr, Gene’s bride. Eleanor had graduated from the all-girls school, and Sandy, still finishing her degree, had come up for Thanksgiving break in New York. Eleanor and Gene introduced Sandy to Hunter at a bar.
“I had a fiancé at the time,” Sandy recalled. Hunter bird-dogged her. “I was flattered but not yet smitten and after all I had a fiancé.”
The next time they met, in 1959, Sandy was on a date with Hunter’s old friend from Louisville Paul Semonin, who was studying in New York and spending a lot of his time living in Hunter Thompson–like isolation in the New Jersey woods. At some point during the evening at the bar, Semonin climbed onto a table and began dancing.
That gave Hunter the opening he needed. He slid onto the seat next to Sandy. She was beautiful: with an open face, blond hair, and tight sweaters and short skirts that flaunted her figure. When speaking to women, Hunter could make them feel as if they were the center of his universe. His eyes bore into theirs, and while they spoke, he drew thoughtfully on his pipe, often nodding in agreement with what they said. It was an act, his friends said, and it often worked.
It had not worked immediately with Sandy. Friends didn’t think calm-and-quiet Sandy could be interested in Hunter. Moreover, there was the fiancé thing. And here she was, on an innocent date with Semonin. She had earlier been set up on a blind date with another Louisville transplant, Ralston Steenrod, studying at Princeton. She joked that everyone she met in New York seemed in some way to be orbiting Hunter Thompson. As a stable young woman, she seemed ill matched with noisy prankster Hunter. After she moved to the city, she was drawn into Hunter’s world. The fiancé was forgotten. That Sandy was quiet and nurturing was in her favor.
Virginia Thompson fronted her son his plane fare, and he arrived in Puerto Rico the first week of 1960, ready once again to start over. It didn’t seem that the job would be that hard, and Hunter thought he might have stumbled into the best situation he could expect, considering his checkered employment history. The Puerto Rican life was good. He rented a beach shack (a pillbox, he called it) and began each day with a bracing swim in the ocean and a stroll down the beach. Unfortunately, he eventually had to go to work.
Kramer had talked a good game during Hunter’s New York interview, but Sportivo didn’t have a chance of being the Sports Illustrated of the Caribbean. It probably couldn’t even be the Sports Illustrated of East McKeesport, Pennsylvania. Bowling was the new fad in Puerto Rico, and Hunter’s assignment was to hang out at bowling alleys and write pieces filled with names of the local bowlers. He was a stenographer, not a journalist. And he was a stenographer for a bunch of bowlers, for God’s sake. It was humiliating for someone with Hunter’s ego and ambition.
After the job, Hunter’s primary concern was clothing. “If I were anything but a writer,” he wrote Sandy, “I couldn’t get away with the way I’ve been dressing down here in this very formal, over-priced Valhalla.” He wrote his mother, begging her to send him his brother Davison’s hand-me-downs or to find any bargains she could scrounge up: shirt size, 15-35, pants, 34 waist.
He wasn’t prepared for the insane cost of living on the island, and the familiar financial panic set in. It was like Cuddebackville all over again, with a warmer climate and the distraction of a tedious job. It took only a few weeks for Hunter to conclude that he had made a monstrous mistake. His initial good impression of Kramer evaporated, and he claimed he was working for “a liar, a cheat, a passer of bad checks, a welshing shyster.”
He got in touch with his friend at the Star, Bob Bone, and showed up at the newspaper office to meet pen pal William Kennedy face-to-face. He also met business editor Fred Harmon, who informed Hunter that there was no candy machine in the office, but he was welcome to kick in the cigarette machine.
In the meantime, Hunter managed to interest Mark Etheridge, editor of his hometown paper, the Courier-Journal, to list him as a Caribbean correspondent. He also sold a couple of pieces to the New York Herald-Tribune, and single pieces to the Milwaukee Journal and Baltimore Sun. He sold and resold essentially the same tourist story to editors of travel sections in mediocre newspapers across America. He even earned a few bucks here and there as a male model.
Still, despite the work and Kennedy, Bone, and his other new friends, Hunter was lonely, so he reached out to Paul Semonin and encouraged him to make the jump to the Caribbean. Semonin landed a job as a proofreader on the San Juan Star, and he and Hunter rented a concrete-block beach house for fifty dollars a month, in the remote village of Loiza Aldea, seventeen miles from San Juan. The roads were so bad and the swamps so fetid that it took an hour to get into San Juan. Hunter and Semonin were the only gringos in the village, and the place had lots of drawbacks. But the little shack had a great selling point: it was in a paradise, right on the beach.
Semonin’s company was not enough to assuage Hunter, and he peppered Sandy with letters, urging her to join them. She had steady, if unglamorous, work as a secretary, but she liked adventure. Hunter found that the distance was eating at him. He was used to women throwing themselves at him and offering testaments of devotion. By this time, Sandy had learned to adore Hunter, but she didn’t want to limit herself. He wrote to her, making it clear that although he had no problems telling her about the many women in his universe, he expected different behavior from her. If she had these adventures, he wrote, “have the simple goddamned decency not to write me about it.” When there was a lapse in correspondence, or when he couldn’t reach her by phone at four in the morning, he flew into a rage. She had grown into him, and he shook with jealousy. At first, he’d had a do-what-you-want attitude about her coming to Puerto Rico. That soon turned into a demand. “I want you to come down here and, if you do nothing else, merely lie naked with me on this living room bed and stare at the sea until I get carted off for jail.”
By May, Sandy was living with Hunter and Semonin in the Loiza Aldea shack. Hunter introduced Sandy as his common-law wife. They were comfortable with that for now. Clothing was optional in their beach shack, and they drank rainwater, ate rice and spaghetti, and downed as much rum as they could manage.
The quarters were so tight and Hunter and Sandy were so relentlessly sexual that Semonin was uneasy. After all, he had dated Sandy first. Considering the circumstances, Hunter and Sandy could have used an infusion of couth, he thought. He was grateful that his job on the Star allowed him to escape five nights a week to San Juan on his motorscooter.
Disenchanted with Sportivo, Hunter worked the freelance market and sold the Courier-Journal a story on Paul Semonin, favorite son of Louisville, working in an island paradise to perfect his craft as a painter. He did this without Semonin’s knowledge or cooperation. When Semonin learned of the piece, he was furious. There had been no formal agreement between them to write an article, particularly something that would be read by friends and family back home. The quotes were only distant ancestors of things Semonin had said in casual conversation at the shack, and some were entirely fabricated. When he confronted Hunter with both the invasion of privacy and the faked quotes, Hunter merely shrugged. To him, it was no big deal.
Stiffing a restaurant on a tab and spending a night in jail also was no big deal to Hunter, but it was to Semonin. “He had a need for histrionics and embarrassment,” Semonin said. “I went to jail with him in Puerto Rico because we jumped a check in a restaurant. Hunter took me out to dinner. We went to this restaurant and ate. He didn’t have any money to pay for it. I didn’t have any money at the time. So we left the restaurant, and finally the owner called police and they found us walking back to our beach hut and arrested us. They put us in the jail in San Juan. And the thing I remember about this is Hunter, at three o’clock in the morning, standing before the judge and answering the judge’s request about whether we had something to say. And Hunter was talking about how the police were Nazis and that it was an outrage that we were treated this way. He immediately projected it into an extreme, fascistic act. Looking back, that was the model for what I’d call his paranoia. But it’s much more active than paranoia, because he creates the drama and escalates everything to a point that’s far beyond the realm of reality. It goes back into that impulse he had for street theater.”
Luckily Hunter had Bill Kennedy as a friend. “I got a call and got some money to the people in authority and bailed those guys out in the middle of the night,” Kennedy said. But the incident infuriated Semonin, and he began to fight Hunter’s gravitational pull.
Hunter started to shape a story around his life in the shack and the three roommates, the sleazy world of cheap journalism on the island, the night life at bars, and the inherent racial conflicts. He made notes and, even though he had no success with his first novel, was beginning to plot his second
Semonin fled to the Virgin Islands to hook up with another Louisville friend, Harvey Sloane. Tired of Puerto Rico and looking for another adventure, on a whim Hunter and Sandy joined them. Hunter and Semonin then hatched a plan in St. Thomas to travel by freighter to Europe. They were mulling this plan over drinks when they met charter boat captain Donald Street. He had a 55-foot sailboat and asked Hunter, Sandy, and Semonin whether they wanted to crew with him as far as Bermuda.
It sounded like a good idea at the time. Sandy and Semonin jumped in, doing whatever Street asked them to do. Hunter, on the other hand, did not cooperate. He’d had enough orders in the Air Force to last him a lifetime and didn’t need Street barking at him. They were at odds from the moment they set sail. The Isle Aire was a 55-foot schooner, and the presence of two sulking men trying to avoid each other made it the most uncomfortable 55 feet in the hemisphere.
By the time the voyage ended in Bermuda, Sandy had had enough, and returned to New York. Hunter and Semonin stayed, trying to get on a freighter for Europe, but no captain considered them seaworthy.
Marooned in Bermuda with no money to escape, Hunter passed his twenty-third birthday, feeling older than most of the people he knew. “If I could think of a way to do it right now,” he wrote his mother, “I’d head back to Louisville, sit on the porch drinking beer, and drive around Cherokee Park for a few nights, and sink back as far as I could into the world that did its best to make me. . . . [T]hanks very much for giving me a good home and a happy, hectic childhood that I never tire of remembering.”
Hunter was able to turn his plight into a piece for the Royal Gazette Weekly (“They Hoped to Reach Spain but are Stranded in Bermuda”). Desperate after three weeks—and by that time living in a cave on the outer reaches of Hamilton—Hunter wrote to the McGarrs, who were in Spain. Gene was on a Fulbright grant, studying Spanish culture. He wasn’t rolling in dough, but still managed to send $200, asking that Hunter pay him back in a year, when he needed to come home.
Hunter, Sandy, and Semonin reunited in New York. Sandy got a job with United Airlines, Semonin resumed his art studies, and Hunter drew a couple of freelance assignments from the Herald-Tribune. On August 1, Hunter appeared as a contestant on Johnny Carson’s game show Who Do You Trust? winning $50, though losing the big ($300) money by being unable to identify the inventor of penicillin.
He began writing a novel drawn from his months in Puerto Rico. The Rum Diary also paralleled his experiences, but strayed more from the strict autobiographical territory of Prince Jellyfish. It gave him a chance to write about the sleaziness he’d found in the bowels of journalism and to set the story in an exotic, though not idealized, island locale.
Once again, though, no one was paying him to be a novelist. He hadn’t given up on Prince Jellyfish, which he sent to Grove Press with a note calling his book “at best, a minor novel.” Again rejected with a form letter, Hunter was furious, not just that his manuscript was rejected but that his solitary nocturnal hours didn’t merit a personalized reply. Though each rejection stung, Hunter felt greater pain when William Kennedy was blown off by a publisher. While putting himself through the daily grind on the San Juan Star, Kennedy, like many journalists of his generation, took a day job in journalism to pay the bills until he would be able to live off the income of his real writing. Hunter admired Kennedy’s work, and when Kennedy’s The Angels and the Sparrows was rejected, Hunter became cheerleader. He was a treasure trove of rejected-writing statistics and told Kennedy not to despair; Patrick Dennis’s Auntie Mame had bounced around like a ping-pong ball before finally finding a publisher.
Perhaps because Kennedy was already over thirty, Hunter felt more desperation for his friend than for himself. Hunter saw himself as not quite ready for the big leagues; Kennedy, on the other hand, was. Kennedy was an artist, and each of his rejections hurt Hunter as much as—if not more than—one of his own. “I’ve compromised myself so often that I can’t honestly see myself as a martyr anymore,” he wrote Kennedy. “You approach your writing more honestly than I do mine.”
By the end of summer, Hunter was ready to blow the city and had enlisted Semonin as partner in a plan to go cross-country for a Kerouac On the Road experience. Semonin arranged the job: driving a Ford Fairlane to Seattle for its new owner, picking up hitchhikers along the way. Hunter saw the trip as being rich with story potential. Sandy, for her part, decided to head to Florida in the fall to work in her mother’s travel agency and join Hunter, once he’d found refuge on the West Coast.
By the end of September, Hunter and Semonin were on the road, taking the Fairlane through Louisville on their way through the Great Plains and the mountains, before finally reaching the Pacific Northwest. The country was in the middle of the Kennedy-Nixon presidential campaign, and Hunter witnessed a Kennedy campaign speech during a stop in Salt Lake City. Later, he took a freeway exit to watch the first Kennedy-Nixon debate on TV in a tiny village near Salem, Oregon. It proved to be a watershed moment. “That was when I first understood that the world of Ike and Nixon was vulnerable . . . and that Nixon, along with all the rotting bullshit he stood for, might conceivably be beaten.” Until that moment, Hunter later recalled, it had never occurred to him that politics in America had anything to do with real human beings.
After delivering the car, Semonin and Hunter hitchhiked south to San Francisco, where they stayed in John Clancy’s apartment. Clancy had finished up at Columbia Law School, where he had served as a temporary landlord/roommate for Hunter, and worked in the Bay Area. He had moved to Berkeley, preparing for marriage and military service. He was happy to let Hunter and Semonin use up the last few days of the lease on his San Francisco apartment. Hunter inhaled the remaining seeds and stems of the beatnik movement, going to City Lights Bookstore, North Beach, and other ports made famous by Kerouac, Ginsberg, Corso, and the gang.
“I have still not decided if San Francisco is good or bad,” he wrote Sandy. “Whether it is or not, I’m hitting the streets Monday in search of a job. My fortune now rests at $9. If you have any extra money, please send it along.”
He was across the continent from Sandy and felt that he had merely exchanged poverty in New York for poverty in San Francisco. It was a foolish move, he thought, but then most of his moves had been ill advised. “I wake up each morning without more than a vague idea of where I’ll sleep that night,” he wrote Gene McGarr, while begging an extension on repaying the $200 he borrowed to flee Bermuda. “I am continually hungry, I have been arrested for shoplifting (a package of cheese—my only attempt at theft, so far), and, as far as I can see, I still have no prospects for a job.”
Hunter spent a month trying to find a writing job, but San Francisco was as talent rich as New York, and he didn’t see many alternatives besides killing himself (spectacularly, of course, in a planned dive off the Golden Gate Bridge) or a midwinter hitchhike across the continent that would throw him into an irretrievably foul mood.
Semonin was worn out from nearly a full year with him, so Semonin vowed to stay in San Francisco and scrounge. “Whatever happens will be all right,” Hunter assured Sandy. “I do not care and I have no plans. I’ll go as far as the rides take me, sleep on the beach and beg, if necessary, for food.” But Hunter had been reading Henry Miller and was full of the romance of what he saw as the ideal writers’ colony of Big Sur, 150 miles south of San Francisco, pushed up against the Pacific by a narrow band of mountains.
Hunter was the product of all of his influences: the big guns, like Hemingway and Fitzgerald, were fairly obvious as major shadows over his writing. The stark Hemingway style (“He walked back to the hotel in the rain”) echoed through Hunter’s writing all of his life. As a social critic, Hunter learned from Henry Miller’s writing. A generation earlier, Miller had documented his love-hate relationship with America, much as Hunter would at the end of the twentieth century. Throughout his expatriate years in Paris—during the Great Depression, not during the glamorous twenties of Scott, Zelda, and Ernie—Miller wrote Tropic of Cancer, the book that was banned in his home country until 1961. (It was published by Obelisk Press in Paris in 1934.) The deep eroticism of the novel made it notorious, but stylistically it was a combination of fiction and fact that Hunter would adopt in his own writing.
Yet the frank sexual language and images in the book overshadowed Miller’s statements of philosophy, his manifesto as an American writer. If we didn’t know this was Henry Miller writing, we might think this was a job description for being the young Hunter Thompson:
I am a free man—and I need my freedom. I need to be alone. I need to ponder my shame and my despair in seclusion; I need the sunshine and the paving stones of the streets, without companions, without conversation, face to face with myself, with only the music of my heart for company.
Miller returned to America just as the Second World War was beginning in Europe. In a cross-country trip, he examined the remnants of the country he’d left a decade before and wrote The Air-Conditioned Nightmare, a book explicit not about sex but about the faults he found in his fractured homeland. Hunter would come to share Miller’s belief in America’s potential in the face of the disappointing reality. As Miller wrote,
I had the misfortune to be nourished by the dreams and visions of great Americans—the poets and seers. Some other breed of man has won out. This world which is in the making fills me with dread. . . .
The most terrible thing about America is that there is no escape from the treadmill which we have created. There isn’t one fearless champion of truth in the publishing world, not one film company devoted to art instead of profits. We have no theater worth the name, and what we have of theater is practically concentrated in one city; we have no music worth talking about except what the Negro has given us, and scarcely a handful of writers who might be called creative.
At the end of his cross-country trip in 1940, Miller found Big Sur, which he called his “first real home in America,” even though he was born and had grown up in Brooklyn.
Although Hunter admired Miller’s writing and was his neighbor across the steep cliffs on the coast, they never met.
A tapered wilderness strung along State Highway 1, the Big Sur peninsula had a history of attracting writers and rebels, from Robert Louis Stevenson and Jack London, up through Miller and John Steinbeck.
It was rough country, and not just the land could be inhospitable. Some of the residents were cranky. There were wild boar in the woods. People like Henry Miller came to Big Sur mostly to hide out. Strangers usually remained that way. Hunter had moved to Big Sur because of Henry Miller, but despite waiting by Miller’s mailbox daily, hoping for a casual encounter, he never met the writer.
Hunter found a cabin for rent and then, as 1961 was beginning, fell into an opportunity as caretaker for property owned by the Murphy family. The land included an assortment of hot sulfur springs offering Pacific vistas and several shacks tossed into the woods. There was the big family house and the caretaker’s cabin, where Hunter would live and fulfill his duties as guard for the wilderness estate.
Having a Big Sur return address raised his literary profile. Though he had no real success, he had the isolated lifestyle of the working artist and he was among them—not just Miller, who lived nearby, but also Dennis Murphy, whose novel The Sergeant had been a raging success and quickly sold to Hollywood. Murphy was pals with Jack Kerouac, and Big Sur was the weekend refuge of the Beats. Hunter felt he had currency from the address to write a how’s-it-going note to J. P. Donleavy and ask what he was up to. There was no answer.
Finally, after a year on the road with ever-changing addresses, Hunter had found a home. He sent for Sandy.
“It was one room on top of the other and with a big window that looked out onto the ocean, out and down, just right on the edge of a cliff,” Sandy recalled. “Fifteen dollars a month. It was paradise. And he worked and he worked and he worked. He absolutely worked every night and every day. He was very serious . . . very serious.”
Hunter also took his caretaker duties seriously. The open-air baths on the Murphys’ land had drawn homosexuals from San Francisco for years, and Hunter took it upon himself to roust them from the baths—just as the night was settling down and the couples felt themselves at peace with nature. Suddenly, a howling, jibbering, gun-toting madman would emerge from the woods and frighten them off.
As caretaker, Hunter also felt he needed to be armed. Through Jo Hudson, a local sculptor, he’d developed an interest in weapons. Like most boys growing up in Louisville, Hunter had a small rifle. But he never hunted until he met Hudson. The artist knew where to find game. Guns seemed a natural accoutrement of a gentleman-crazy in Big Sur. So did dogs—the larger the better. He and Sandy got a Doberman pinscher named Agar and beheld the sunsets from their vistas in the Santa Lucia Mountains over the Pacific, where occasionally they could watch whales migrating south. Clothes were largely optional in Big Sur, a policy Hunter and Sandy embraced.
There were other friends as well. Singer Joan Baez was also a new arrival in Big Sur, where bargains could be had. “For thirty-five dollars a month, we rented a cabin consisting of one bedroom (doubling as a living room), a tiny bathroom, no closets, and a kitchen,” she wrote in her autobiography. “We had four dogs and many cats.” Primitive life meant no telephone—and that made booking concert dates difficult.
Baez and Hunter were not friendly neighbors at first. Ever the pacifist, she was put off by his guns and boisterous behavior, and the more he realized that his behavior irritated people, the more he ratcheted up his antics. Eventually they developed a fondness for each other, but it took a long time.
Hunter also befriended Lionel Olay, a middle-aged freelancer eking out a hand-to-mouth existence on Big Sur. He had written the thirty-five-cent paperback pulp fiction classic The Dark Corners of the Night. Olay’s life-given-over-to-writing inspired Hunter deeply. Olay never seemed to worry about money. The work came first. Olay also gave Hunter the model of a don’t-give-a-shit writer who didn’t worry about offending sources or stepping on editors’ toes.
For the first half of 1961, Hunter and Sandy shared their cottage on the edge of a cliff overlooking the ocean. The Murphy property was being reinvented that spring as the Esalen Institute, which was to be a nonprofit think tank where out-of-the-mainstream writers, artists, and philosophers could come together, hang out in the hot baths, and solve all of the world’s problems. Esalen would end up drawing Aldous Huxley, Joseph Campbell, Kerouac, Ginsberg, Baez, and others who gathered there to “explore human potential.” That’s what Michael Murphy—member of the property-owning family—and his friend Dick Price had in mind. Esalen took its name from the Esselen tribe that used to live on the point. As the touchy-feely think-tank idea was being developed and renovations made to some of the structures on the property, Hunter and Sandy looked after the day-to-day maintenance.
“We were living in the servants’ quarters of the big house at the Esalen property,” Sandy remembered. “On the Pacific. It was wonderful.”
It was wonderful, of course, as long as she maintained her role of being subservient to Hunter. Their relationship had fallen into a pattern in which all aspects of their lives were directed toward Hunter’s work. He saw the job as caretaker as an entitlement to live on the spectacular California coast. Hunter wrote all night, slept much of the day, and when he woke, Sandy’s job was to take care of him. So any true caretaker duties also fell to her.
For the first several months, his writing contributed nothing to the family income, so Sandy spent those hours when Hunter slumbered working as a maid. She also made the three-hour drive to San Francisco twice a week to do temp work. Some neighbors found her role as Hunter’s slave offensive. He acted like a man who expected servitude. They fought, and sometimes Hunter slapped Sandy. Since he slept through much of the day, her job was to keep the world away. When he awoke, usually after noon, she’d make breakfast and he would sit overlooking the ocean, smoking, drinking coffee, reading newspapers, and often reading what he’d written during the night. He sometimes asked Sandy to read aloud what he had written, but did not expect criticism, only vindication.
He’d begun referring to The Rum Diary as “the Great Puerto Rican Novel,” believing he was into semivirgin terrain, since the only Western writer mining Latin America was Catholic-obsessed Graham Greene. Hunter believed he could look at that part of the world with his new sensibilities and unflinching eye, avoiding the sort of religious moralizing that marked Greene’s books.
But the publishing world took no notice of his work. He had written off Prince Jellyfish after it bounced all over Manhattan, but he felt that by going to somewhere foreign, The Rum Diary had more chance of success. He constructed a story with more scope and ventured outside the raging and superior interior monologues of Wellburn Kemp, the “Jellyfish” protagonist.
“The big money is just around the corner,” he wrote to Ann Schoelkopf, “and it won’t be long until I get my hands on it.” Given his faith in himself and now with the luxury of time and reliable, spectacular shelter and a nurturing environment, Hunter felt poised for success and recognition.
Semonin had given up on California and landed in Aspen, Colorado, just before Christmas 1960. He wrote Hunter, beckoning him to the mountains, where he would find the beauty and isolation he needed to write. Hunter made a brief visit, having cadged a small assignment that paid his way: delivering material to a decorator. He showed up at the home of local writer Peggy Clifford, with whom he began a friendship. “It was snowing, and I showed up on Peggy’s doorstep,” Hunter said, “a freak from Kentucky with a pile of trash on top of a car that had to be delivered to some decorator in Aspen. I thought Peggy would be horrified. . . . Peggy fed me, gave me a place to sleep, money for the train when the decorator quibbled, and a ride to the train in Glenwood Springs. Here came a vagrant through town, a Neal Cassady kind of freak, traveling with a giant Doberman and a monster crate that was heavy and made to be a home for the dog on the train, if we ever got on the train, and she took care of everything.”
Hunter filed it away; Aspen was good, but he and Sandy were on a roll in Big Sur—living in the servants’ quarters, raising a Doberman, writing, seeing the sunset over the Pacific . . . it was all too good—for Hunter, at least.
“When we were in Big Sur, I got pregnant,” Sandy recalled. “I had two abortions. In Mexico. There was never any question in my mind, both times. We were very poor. We were not at all ready. Had I had either of those children, Hunter would have had to have left me.”
While Sandy tiptoed around Hunter, waited on him, made sure he had a quiet, child-free home in which to work, rejections piled up. Unhappy that he wasn’t getting any publications, he decided the problem was with his agent. On Olay’s recommendation, he wrote Sterling Lord, agent for both Kerouac and Mailer, sending him a sampling of his writing, offering details of his lack of success, and bemoaning that he was sinking into a bog of poverty.
For a quick paycheck, Hunter retreated to journalism. If the publishing world was ignoring his fiction, he thought he could build a track record in magazines and work from there. He realized he was in the middle of a world about which the rest of America might be curious, so he began pitching an article on Big Sur to Playboy. Infuriated when his article was rejected, Hunter pitched the piece to a rival men’s magazine, one that was a whole lot sleazier, and was shocked when it was accepted.
Hunter had his first publication in a national magazine and $350 to show for it. When Sterling Lord rejected him, Hunter fired back a brutal letter (he called him pompous and moronic) and crowed that he was finally on his way.
“Big Sur: The Garden of Agony,” appeared in Rogue in the summer of 1961. Although it didn’t have gratuitous first-person references, it was clearly Hunter’s voice and attitude. Mostly, he dealt with myths and realities of Big Sur: the free love, the wild sex, the baths, the orgies, the general wildness of the continent that had been shaken down at this ragged edge by the sea. He used his friends as sources and put his observations into the mouth of a character he called “the writer.”
The piece also dealt frankly with Henry Miller and the shadow he cast over the area. Several of Miller’s books, including The World of Sex, had yet to be published in America. But Tropic of Cancer was available overseas and was carried in haversacks back into the states. It was enough to encourage literary groupies and sex nuts to trek cross-country to knock on the writer’s door in the middle of the night. Miller was a prisoner of his audience, many of whom came to him as the one who lived out their fantasies.
The Big Sur article pissed off the community, as if Hunter had disclosed family secrets—and, in a way, he had. He’d referred to the community as “a Pandora’s Box of human oddities.” There were also those who felt the article would increase the influx of sex-crazed morons into the area (Rogue, after all, didn’t have the literary credibility of Playboy). There was the stuff about the popularity with homosexuals, which was not considered a good selling point in 1960. “He wrote about some baths which were on the property, which was a haunt for gay people,” Sandy said. “And in those days it was hard—it was hard for the landlady to hear.” And by painting the area as a sex-and-deviance theme park, Hunter had deeply offended the dominant family and added more fuel to the fire.
The Murphys’ grandmother, Vinnie, owned the estate and was not pleased. The Rogue article was a mixed blessing: it was Hunter’s first national publication, and it was also the reason used to evict him.
It had been nearly a year of peace and solitude, longer than he had any right to hope for, considering his track record. Unable to find another cabin to rent, he decided to return home, to his mother, to the peace and sanctuary that he needed to finish The Rum Diary. Sandy went ahead to New York. She planned to stay with friends and work as a secretary to contribute to the Hunter Thompson Survival Fund.
Back home on Ransdell Avenue, Hunter labored to finish his book. He’d sold a short story (“Burial at Sea”) to Rogue, his first published fiction, but he was angered when the editors chopped hundreds of his words. He’d accepted their suggestions with the Big Sur article, but he was fiercely protective of his fiction. Louisville was “grey and wet and full of so many ghosts and memories that I get the Fear whenever I go outside.” He secluded himself with his novel and pitched articles on conservative politics and bluegrass music to various national magazines, most of which declined the honor of publishing them. He made a brief trip to eastern Kentucky for a winter music festival and sold a piece to the travel section of the Chicago Tribune, another major-newspaper publication to add to his résumé.
He stayed home through the holidays but by January was back in New York with Sandy, plotting his next move. He felt that Latin America was underreported (or ineptly reported) in the North American press, and he likewise felt that he was the man to rectify the situation. And he had the means to do so. His grandmother, Memo, had died, leaving Hunter $15,000. He immediately bought a camera and booked passage to South America, prepared to unleash himself on the world as a foreign correspondent.
Before setting up to leave, Hunter spent the winter and early spring of the year finishing The Rum Diary (he called it “a book of flogging and fighting and fucking”) and handed the manuscript over to his new agent, Candida Donadio. By the time he was finished, he had come to think of the book as a waste of time, especially after reading Isak Dinesen’s Out of Africa, which he considered a masterwork. He and Sandy had farmed out most of their possessions and were sleeping on a mattress on the floor of a shabby apartment.
He wondered why he chose to put himself through such a life. “I’m damned if I can figure out why people keep at it,” he wrote Lionel Olay. “Like most young writers, I am a natural ingrate and will always think that my work and my views are above and beyond advice—at least until I finish one thing and can get far enough away from it to see it clear and mean like a girl who drives you mad when you’re drunk and then looks like hell in the morning.”
He had Sandy, but he was addicted to womanizing. Time, as he saw it, was the enemy. “I am plagued with a mounting suspicion that time is going to force me to leave a lot of women undone,” he told Olay. “There is just too goddam much to do and too many places to be all at once. There are nights when I want to be in San Francisco and New York and Rio and Madrid at the same time, and it seems unjust that I can’t. If I had my way, I’d be in love all the time all over the world with a rifle in one hand and a typewriter in the other and a bellyful of good whiskey.” To Bill Kennedy, he wrote, “A beautiful woman is such a wonderful creation as to make all novels seem like scum. It is enough to make a man believe in god.”
Hunter had accumulated another trunkful of letters and manuscripts, which he sent home to Louisville. He asked a fellow Doberman lover to take care of Agar (“When a person spends as much time on the move, as I do,” he wrote, explaining his concern for the dog, “he becomes more than normally attached to the few tangible things he can call his own.”) Boarding Agar became local news, and the Courier-Journal ran a story about Hunter’s concern that the dog’s separation from his master could be emotionally detrimental. “It can be tough to have a globetrotter for a master,” the newspaper reported, calling Hunter “a writer whose wanderlust sometimes takes him . . . on short notice.” Sandy was staying in the city, providing some stability for his life thanks to her secretarial job with Nuclear Research Associates, a firm based in Queens. Scientists there manufactured amphetamine on the side. Considering what Hunter had in mind for Sandy’s role in their partnership, it would come in handy. Hunter’s plan was to write travel stories that he could send off to a variety of American newspapers, where travel editors lived on freelance copy. Hunter intended to send his stories to Sandy, have her type several copies of each, and serve as his freelance manager. With all that typing, the speed would be vital.
Finally, on the evening of April 24, Hunter set off for South America. It would be from that far-flung locale that Hunter’s voice was finally heard in American journalism.