It is also requested that Airman Thompson be officially
advised that he is to do no writing for any kind for internal
or external publication. . . .
—Air Force memo, August 23, 1957
He was afraid of electricity, and they wanted to turn him into an electrician.
To Hunter, it symbolized his problem with military service . . . or of any confrontation with authority. Whatever they wanted, he opposed. Considering the confines of indentured servitude in the armed forces, Hunter might have wondered whether it was a better choice than jail.
But he had had few options in Jefferson County Jail. He got a month knocked off of his sentence for good behavior, but this good news was delivered by Judge Jull with an ominous warning: “We’ll be watching you.” He served notice that until Hunter was twenty-one, he would be allowed to breathe but not do much else in Louisville, Kentucky. Hunter got a job driving a truck for a furniture store and almost immediately backed the truck through a showroom window. The cops showed up and Hunter decided it was time to begin his military career. It was either that or jail, he figured. He walked to the Army recruiting office, but was told he’d have to wait. At the Air Force recruiting office down the street, there was no cooling-off period and he could enlist immediately. Finally, he was leaving home. “Louisville is a good place to grow up and a good place to get away from,” he said.
Hunter first put on the crisp khakis of the U.S. Air Force in the late summer of 1955 and arrived drunk at Randolph Air Force Base, in San Antonio, impressing his drill sergeant by vomiting during his first roll call. During basic training, he rose early, ate bad food, answered to his supposed superiors, and quickly mastered the art of simmering resentment.
The Air Force decided he would make an excellent electronics technician.
But I want to be a pilot, Hunter told them. Why else would I be in the goddamn Air Force?
You will make an excellent electrician, the Air Force decreed.
And so after basic training he was sent to Scott Air Force Base, near Belleville, Illinois, across the Mississippi River from St. Louis. He spent a miserable six months at Scott, but squandered many of his off hours in the Pine Room Tavern in Mascoutah, a village just south of the base. He’d drink a pitcher of frigid beer and dine on fifteen-cent hamburgers supplied by a laissez-faire bartender who kept the bar open, even with Hunter as the only customer. Hunter spread his supplies over the counter—books, papers, pens, cigarettes—and wrote letters to his friends and family. Some friends were still back in Louisville, and some off at Ivy League colleges. He’d made friends in the Air Force, but he was still lonely, missing his old running buddies and their adventures. He sat at the counter of the miserable bar in the middle of Bumfuck, Illinois, and wrote sentimental letters to his lost friends, angry diatribes at the mongrel dogs who controlled his life, and pleas for forgiveness to his mother. Back in jail, filling pages of notepaper, he’d discovered the therapeutic effect of writing. In jail, he wrote his mother daily, admitting that he had gone too far and brought her shame. He also wrote to his friends and composed assignments for a correspondence course.
There was volume and desperation in his writing. He wanted to keep his friends, and he worked hard at it, writing several long letters a week. “I find that by putting things in writing I can understand them and see them a little more objectively,” he later wrote. “I guess that’s one of the real objectives to writing, to show things (or life) as they are, and thereby discover truth out of chaos.”
He maintained the letter-writing habit his whole life and, sitting at the Pine Room’s bar, wrote his mother newsy letters, full of optimism. If he resented his friends going off to college, he didn’t write it down. Hunter could not be described as being content with his life, but he was ripe with ambition and fully prepared to deal with the obstacles a military stretch threw at him. He faced problems by drinking. He later told a friend he was intoxicated for much of his six months in the Land of Lincoln. It didn’t help matters that he was fairly close to Louisville and could go home to drink with his friends who had stayed in town and to entertain those same friends when they drove to Illinois.
Hunter was picked as a promising electronics technician because he aced the Air Force radio-tech exam. Hunter shrugged off the triumph. Tests were easy. You didn’t need to know about radios and electronics; you just needed to be savvy in answering multiple-choice questions. He scored so high, the military thought he was the second coming of Marconi. But Hunter hated working with any kind of electronic or electrical component because he feared electrocution. In all-night classes in intelligence electronics, Hunter tried to deal with his fear by giving surreptitious electronic shocks to his classmates—and himself. The minor pain he felt was offset by watching his fellow airmen jump. This warped joy was his introduction to his new friend, electricity.
“Electricity is neutral,” he wrote years later. “It doesn’t want to kill you, but it will if you give it a chance. Electricity wants to go home, and to find a quick way to get there—and it will. Electricity is always homesick. It is always lonely. But it is also lazy. It is like a hillbilly with a shotgun and a jug of whiskey gone mad for revenge on some enemy. . . .”
Squadron commander Ted Stephens battled with Hunter over his pranks, his work ethic, his attitude, and his drinking. Although he could have busted Hunter, he chose to give the eighteen-year-old airman a second chance . . . and a third . . . and they lost count after five. Hunter was stunned. If Stephens had followed the manual, the insubordinate airman would have been in the stockade. But Stephens kept giving Hunter more chances, which he eventually screwed up. Still, Stephens didn’t throw the book at him.
Stephens was a rarity. Hunter quickly earned a reputation as an attitude case around the base. He didn’t fit into the military mold, and since he was popular with fellow airmen, officers began to worry that he might spread his malcontent ways.
Hunter also went through military-intelligence training at Scott but refused to accept a security clearance from the Air Force. “I didn’t honestly consider myself a good security risk, because I disagreed so strongly with the slogan ‘My Country, Right or Wrong.’ ” Nevertheless, he graduated from that program and somehow managed to pull the seemingly plum posting at Eglin Air Force Base, the huge installation in the Florida Panhandle between Tallahassee and Pensacola. Eglin was almost the size of a New England state. The nearest civilian outpost of any size was Fort Walton Beach. The beach near Eglin was desolate and beautiful. The base was just south of Alabama and closer to the Deep South than other parts of Florida, which was still more than a decade away from becoming the theme park capital of the world. Much of the Panhandle was wild and the beaches were dangerous; airmen who went swimming were sometimes pulled into the Gulf by the riptide.
Hunter was posted to Eglin in July 1956. He had feared ending up a fail-safe toggle-switch jockey in the Arctic Circle, controlling mankind’s destiny, like his friend from Scott Air Force Base, Ted Peterson. Peterson had outscored Hunter on all of his tests and yet ended up in Anchorage. How did Hunter pull the Eglin gig on the glorious and balmy Gulf Coast? He’d rolled in shit and landed in a field of yellow daisies. Hunter couldn’t help rubbing it in. He wrote Peterson, pretending to beat himself up for not requesting an assignment to Alaska; then he interrupted himself: “That raucous noise you just hear was probably my screech of laughter, floating through the northern pines and across the northern wastelands, and into the smelly confines of your shack.”
That isolated stretch of the Gulf Coast had played a strategic role in the Second World War. The Army and Navy rehearsed for the D-Day landing at Carabelle Beach and the Army Air Corps (it would not become the Air Force until 1947) practiced for General Jimmy Doolittle’s raid on Tokyo by bombing the hell out of the 384,000 acres of Florida woods that made up Eglin. After the war, Eglin’s remote locale made it attractive for weapons and aircraft testing. Locals said it was the East Coast version of Area 51. That sparse region of the Panhandle led the nation in UFO sightings. It was one of America’s largest military bases in terms of pure acreage, and there was a feeling that it was a good place to hide things.
But the plum assignment did not improve Hunter’s mood. He was still surly, resentful of military wheel-spinning. Driving his beat-up clunker back to base one night with a bottle of booze for company, he grew angrier as he neared Eglin. When he reached the front gate, instead of stopping, showing his badge, and saluting the geek drawing night duty, he slowed only enough to give himself a good shot with the bottle of gin. It went sailing past the checkpoint airman and shattered in the guardhouse. The bottle-throwing soon became part of the lore that followed Hunter. Colonel Frank Mears, the base commander, was furious and wrote a stinging reprimand. But Hunter figured, What’s the worst that could happen? They kick me out of the service?
Eglin had an education office, and Hunter thought it might help him crawl out of the hole the Air Force had thrown him in. He signed up for night classes at Florida State University, then still a sleepy college up the road that had recently begun admitting male students. He thought a literature course might be fun, and maybe a psychology course. The director of the education office thought it was interesting that Hunter wanted to take the literature course. They started talking, and Hunter said he hated everything he was doing at Eglin.
“Know anything about sports?” the officer asked abruptly.
“Sure,” Hunter said. “I was editor of my high school newspaper.” He also ad-libbed that he’d covered high school sports for the Courier-Journal. It was a lie, of course.
“Well, we might be in luck.”
An Air Force base was a closed society with its own rules and customs. Huge billboards out on the civilian highways surrounding Eglin were decorated with pictures of looming B-52’s and the slogan “Peace Is Our Profession.” But why advertise or tantalize civilians with messages of welcome? In that paranoid Cold War era, Air Force bases were locked tight.
At five o’clock every afternoon, life stopped on the base as loudspeakers in palm trees blared the national anthem. Drivers pulled over, got out of their cars, and stood at attention. In the base movie theater, where admission was thirty-five cents, the whole audience stood before the main feature, while the anthem played as a black-and-white flag rippled on the screen. After the previews but before the main film started, a short film was shown of an F-105 in flight as a stentorian voice read “High Flight,” a poem written by Gillespie Magee, a pilot killed four days after the Pearl Harbor attack. The poem reveled in flight (I have slipped the surly bonds of Earth) and concluded, “I’ve touched the face of God.” Sometimes the theater was quiet enough to hear young airmen sniffle.
Most of the officers and many of the enlisted men had families, so the Air Force base provided them with shopping, schools, playgrounds, swimming pools, and all the usual accessories of home life. The housing was often wretched, but it was free—part of the package deal of military family life. Mosquitoes swarmed in the Panhandle, but the base helped by sending around a pesticide truck on Friday afternoons, blanketing the neighborhoods in thick clouds of DDT. Children rode their bikes into the fog and imagined they were at war.
And then there was the newspaper. The weekly delivery of the base paper was an event. Children were plucked from school to ride in the back of a pickup truck, roll up copies of the paper, and fling them into the yards as they passed.
After the education officer told Hunter about the sports-writing job, it was a matter of days before he was on the Command Courier staff. He hadn’t been in Florida a full month when Hunter S. Thompson’s first byline appeared in the Command Courier, on August 30, 1956. The transfer to information services changed his life.
For Hunter, working for the newspaper meant freedom. He no longer had to wake to reveille and jump when his squadron commander barked. He had the most valuable commodity an American enlisted man could have: some measure of personal freedom. He set his own schedule. Being a journalist for the base paper was as close as he could come to being a civilian.
“I now have the best deal I could possibly have in the Air Force,” he wrote to Gerald Tyrrell, who was starting at Princeton that month. “Acting the part of the experienced, competent journalist day after day has been quite a strain on my nervous system.”
He had been raised on a diet of old newspaper movies—Cary Grant and Rosalind Russell in His Girl Friday, Jimmy Stewart in Call Northside 777, Edward G. Robinson as the crusty editor in Five Star Final. Too young for legitimate crust, Hunter did his best to act the part: cynical on the outside, idealistic on the inside. I can fake that, Hunter thought.
He flipped through a journalism textbook he found in the base library and learned a few key phrases to help him pass: lede, nut graf, 30. . . . His bosses fell for it. No one checked out his claims of having edited his high school paper or covering sports for the Courier-Journal back in Louisville.
Hunter learned on the job. The writing was easy for him. He loved all the strong verbs, the language of the sports writer, and his stock phrases, his “sportugese.” Hunter wallowed in the terms of the genre. Bowlers were keglers, basketball players were cagers, and football players were gridders. A quarterback was a field general, and a demanding coach was a fiery mentor. He slung his clichés well:
ARMY CAGERS COP 7 OF 1O SPOTS ON TALENT
LADEN ARMED FORCES ALL-STAR HOOP QUINTET
He did a great job of fooling his superiors. In his first few weeks with the Command Courier, Hunter broke most rules of American journalism and the English language. He seemed unaware of Associated Press Style, his spelling was atrocious, and when in doubt, he tossed in random bits of punctuation. His stories were fecund with clichés and sports jargon, and he was innocent of the simple verities of publication design. He edited the sports page as if he were a human shovel, squeezing as many stories as he could into his allotted space. He wrote about golf, motorboating, tennis, boxing, and the base Little League teams. He was egalitarian—officers’ wives and children shared space with airmen’s exploits. The women’s softball team, the Eglinettes, were spotlighted when its “ace hurler” stomped Fort Benning’s WACS, 11–1.
Hunter said writing sports had a huge effect on his development as a writer. “Look at the action verbs and the freedom to make up words,” he said. “As a sports editor, you’ll have twenty-two headlines and not that many appropriate words.” After a while, it grew tiresome to say “Team A beat Team B.” Hunter loved coming up with euphemisms. “At the Air Force base, I’d have my section: flogs, bashes, edges, nips, whips—after a while, you run out of available words. You really get those action verbs flowing.”
The centerpiece of the sports page was Hunter’s column, “The Spectator.” In it, he could write about whatever pleased him: the Kentucky Derby, the last season of the Brooklyn Dodgers, and even the injustice of preventing the best team in college football, the University of Oklahoma Sooners, from playing in the Orange Bowl because of a prohibition of back-to-back appearances. That piece even had a title that would sound at home in Hunter’s writing twenty years later: “Voodoo in the Orange Bowl.” He debuted in “The Spectator” a technique he later used in Fear and Loathing in Las Vegas—the fake editor’s note. To buy himself a three-day leave, he wrote a column as if it had been pieced together in his absence. “The Spectator is on a well-deserved three-day pass. During his absence, flotsam and jetsam of the sports world found its way to the Spectator’s desk. The Courier staff put it together for your perusal. Peruse—on us.”) In Fear and Loathing, he would insert notes in the narrative: “At this point in the chronology, Dr. Duke appears to have broken down completely. . . . We were forced to seek out the original tape recording and translate it verbatim.” The fake editor’s note provided anonymity and allowed Thompson to work an attitude into “The Spectator” that he couldn’t with his regular byline, such as some thoughts on international sports and sharing a golf joke.
“The Spectator” also allowed Hunter to develop another trademark: turning a minor subplot involving himself into an epic. Missing his first Kentucky Derby in years was worth historical comment, and Hunter cast himself in the self-deprecating role he wore so well in his later work:
For the first time in eight years, peace will reign in Box 152 at Churchill Downs on Derby Day. No cries of disappointment, no overturned chairs, no crowd of garrulous fops will trouble that spot. A pair of red-rimmed eyes, throbbing after the inevitable revelry of Derby “gatherings”; a rumpled tan cord suit, misshapen from overwork; a pair of nicotine-stained hands, gripping the rail for support; an enormous collection of mint-julep glasses cluttering the floor—these familiar trademarks will be absent when the crowd of 100,000 stands to sing “My Old Kentucky Home” as the horses parade to the post.
But the historic event will go on, even in the absence of the Spectator, whose previous commitments make it impossible for him to join in the annual ceremonial by the banks of the Ohio. . . .
Home still had a strong gravitational pull. In letters to family and friends, he described the detail of his daily life, writing with Southern-gentleman graciousness to his aunt Lee, and with a more conversational, yet still formal, style to friends. He could be a chameleon. He bulletined a letter to Tyrrell as if his life at Eglin were a lost passage from Dos Passos’s U.S.A. With Menckenesque flourish, he wrote his mother about his job and his classes at Florida State. He wanted her to know he was too busy to get into trouble. He wrote Judy Stellings to ask whether she had his Male High School ring and that if she would send it back, he would steal a model airplane for her. He also asked for her picture.
Aunt Elizabeth worried about him, but he tried to put her at ease. “I have found something which will keep me busy and which is also enjoyable,” he assured her in a letter. “I have been able to keep out of mischief and finally settle myself on an even keel for once.” He even confessed nostalgia. “I’m beginning to feel like my wilder days are behind me.”
He controlled his schedule and made sure it was grueling. No one stood over him to demand that work be done. The freedom made him work harder. During his first two months on the job, he lost twenty pounds and much sleep. He estimated that each day he drank twenty cups of coffee and smoked more than three packs of cigarettes. His pay was $130 a month, which allowed him to announce his presence with authority at the Seagull Bar on the narrow spit of Okaloosa Island, the barrier between the Gulf of Mexico and the mainland. There he drank, smoked, and made off-the-wall bets with the sun-burned regulars.
For the year he worked on the Courier, Hunter was on his own to figure out how to run the sports page. He read the major newspapers’ sports sections that came into the office and soon pared back on hyperbole. Rather than go over the top, he erred on the side of subtlety. He gathered information from several national newspapers, and “The Spectator” column showed no allegiance to Eglin-only sports.
Hunter wasn’t above bragging about his home-state sports heroes (he loved to celebrate Adolph Rupp’s run as head basketball coach at the University of Kentucky) or even bringing his friends into the column. He cadged a trip home to Louisville from the brass in order to cover the Bluegrass Festival, which inaugurated the city’s new coliseum with a basketball tournament. The University of Louisville beat fifth-ranked St. Louis University in a piece Hunter titled “Appointment in Waterloo.” He included an interview with another veteran sports sage—Porter Bibb, sports director of New Haven’s WYBC. He used the worldly-sounding Bibb to heap lavish praise on the Louisville Cardinals.
The weekly grind lubricated Hunter’s prose, and soon he began hacking through the thick sentences and awkward structures. Clichés were trimmed, and he rarely hesitated to unfurl his opinions in his column.
He did more than write. He also had to lay out pages, fit headlines, and take pictures. He became so interested in layout and the need to fight the genetic vertical design of the page—a newsprint page being taller than it was wide—that he designed photographs and stories in horizontal units. He began to take feature pictures to match the spaces he needed filled in on the page, not because they had any real news value.
Hunter was popular with most, but not all, of the staff. “He was a wise guy,” said Joe Gonzalez, who worked alongside him. “He smoked a cigarette in a cigarette holder. And he was quite good at making up stories about things that would happen—that didn’t exactly ring true, of course. I didn’t like him. He was an egotist. He was always one for telling you, ‘In twenty years, you’ll still be writing for a base newspaper, and I’ll be writing best-selling novels.’ That was the type of person he was. He was also kind of a leech. He was always borrowing money from other people and taking trips on their money, and he never paid anybody back.”
Hunter also irritated Colonel William Evans, chief of the information services office, with his rebellious attitude. But that attitude made him a hero to many of his fellow airmen. Instead of the malicious mischief from his Louisville days, his pranks and practical jokes now took the form of fake news releases. In one, Hunter presented fellow airman Gene Espeland as the hot new prospect for the Boston Celtics. In a farewell tribute, as Espeland left the service to return home to Montana, Hunter went over the top:
One of the most colorful athletes to ever wear an Eglin uniform, Gene was what they would call in France “un type.” Here, we call them “characters,” but they tend to be the same the world over, and without them, life would be intolerably dull.
And so, as “The Ace” heads out to Montana, where the dog tracks will undoubtedly welcome him, the list of athletes departing the base gains another name.
Espeland was embarrassed by the attention Hunter foisted on him. “He made up the craziest stories,” Espeland recalled. “A little something would happen in the gym and he’d make a great big story. He had one story where I hit nine forty-foot jumpers, and then he took a picture of me reenacting a ninety-foot jumper that I threw the length of the floor.”
Being a sports writer meant travel and getting off base on someone else’s tab, a godsend gig. He covered practically anything, even sports he knew nothing about. Back then, large military bases fielded football teams, and they traveled to away games in style, and Hunter got to go along. The Eglin team was especially good in 1956, since it featured three future stars of the Green Bay Packers: quarterbacks Bart Starr and Zeke Bratkowski and receiver Max McGee, all of whom had been called up for duty for the Suez Crisis. That year, Eglin beat the Scarlet Knights of Rutgers.
There was enough freedom in the job that Hunter and some of the other Command Courier staff moonlighted for the Playground News, the weekly newspaper in Fort Walton Beach. Later, Hunter liked to amplify his legend, saying he’d pissed off superior officers by breaking a no-moonlighting rule. Not true, said Joe Gonzalez and Bill White, two other airmen on the Courier staff who moonlighted at the civilian weekly. “We both got onto the newspaper exactly the same way,” Gonzalez said. “We both worked on the base newspaper at Eglin and took part-time jobs on the Playground News. You had to get permission from the brass, but moonlighting was okay.”
When Hunter had tired of covering the area’s Class-D baseball team, his Courier colleague Bill White said he wanted the job. “It’s yours,” Hunter pronounced. But White needed something more official in order to get press credentials. With a flourish, Hunter pulled out a piece of Playground News stationery and rolled it into his typewriter. “ ‘To Whom it May Concern,’ ” it started, “ ‘Please admit Bill White’ . . . and so on and so forth, and he signed it ‘Hunter S. Thompson.’ That was my press pass. I carried it in my wallet for years, and I’ve still got it. I never had any idea that Hunter would become as well-known as he did.”
Life was busy. Hunter made weekly trips to Tallahassee to attend classes at Florida State and to romance Ann Frick, a fellow student. He was smitten, and they maintained their long-distance relationship even after his Florida tour of duty ended.
Hunter chipped away at a college degree, two classes each semester, knowing he would never catch up with the Ivy Leaguers he’d gone to high school with back in Louisville. But in his letters there was no resentment of well-heeled friends, and he freely gloated about the life he’d cobbled together as sports journalist in sunny Florida.
However, his superior officers thought he abused his freedom. Statement of the obvious: Hunter S. Thompson and the U.S. Air Force did not get along. Tossing bottles at the guardhouse had irritated the electronics squadron leaders. The fake press releases and news stories infuriated Colonel Evans, chief of the information services office. After several months of Hunter’s horseplay, Colonel Evans began to clamp down.
Hunter embellished his antics for Judy Stellings. He wrote to her in March 1957 that nine sergeants had cited him for insubordination, that he had been arrested for driving a scooter recklessly, and that he had been found drunk on duty. After an “all-night orgy,” he wrote he’d fallen asleep on Colonel Evans’s office couch and was surprised by his commanding officer on arrival the next morning.
There was probably some truth in the story; more likely, though, he was trying to entertain his old girlfriend with an elaborate tale. But his acting-out indicated that he was tired of the military. He told a friend he was weary of service-life hassles. He did not fit into a rigidly structured organization.
But he did well enough on the Command Courier and with most of his Air Force buddies to contemplate trying to advance himself in the military. If he did well on the Courier, he figured, no reason he wouldn’t be a good candidate for the Armed Forces Press Service. That would mean a posting to New York with its bars, bohemians, and women. His first six months as Courier sports editor were productive. But thereafter he started getting into trouble again: drinking, carousing, insubordination born of the freedom that came with the job. He began alienating some of his Eglin friends. Isolated and restless, Hunter fell into a funk.
Good news arrived in the mail. The Athenaeum Literary Association informed him that he had been reinstated as a member of the class of 1955. The news boosted Hunter’s spirits. He gushed his gratitude in a letter addressed to all Athenaeum members:
Of all the things for which I am grateful to the Athenaeum, I think the most important thing I learned was the importance of thinking. Had I gained nothing else, the acquisition of this quality would have made those three hectic years worthwhile. A man who lacks the ability to think for himself is as useless as a dead toad, while the thinking man has all the powers of the universe at his command.
As his relationship with the Air Force spiraled downward, he wrote to a friend, “I don’t feel that it’s all necessary to tell you how I feel about the principle of individuality. I know that I’m going to have to spend the rest of my life expressing it one way or another, and I think that I’ll accomplish more by expressing it on the keys of a typewriter.”
Hunter could say a lot without opening his mouth. He had a smirk, thick with condescension. Elvis would have envied his sneer. His eyebrows rose like arching leeches as each new idea crossed his face. He could maintain the façade of saluting-and-obedient Airman Thompson, but his superior officers were not stupid men, blind to Hunter’s insolence. Hunter thought it best to add some space between them.
Hunter found an abandoned beach house on the Gulf and moved in, dubbing his new pad “Xanadu,” both after the empty and tragic Citizen Kane castle and the stately pleasure dome of Coleridge’s Kubla Khan. (He also adopted “Cuubly Cohn” as one of his pseudonyms for the Playground News, making it appear from the variety of bylines that the News had a large staff.) When Hunter invited friends over for rivers of booze, he did his best to make the rickety house live up to the second meaning.
Despite his crush on Ann Frick at college, he was keeping up other relationships as well. While at a Gulf Coast bar, he’d met and begun a scorching romance with a former Illinois beauty queen named Kraig Juenger. She was married (though separated when she met Hunter) and a worldly woman of thirty-four. Hunter was eighteen. They spent two weeks together at the beach and along the banks of the huge Choctawhatchee Bay, separated from the Gulf of Mexico by the narrow spit of Santa Rosa Island and Destin. The bay, ringed with decaying Southern mansions, was a good place for a couple to lose itself. After her return to Illinois, Hunter pointed his car due north, to visit her home in Collinsville, not far from Scott Air Force Base. But much of the affair was played out in the passionate letters they exchanged, and their obsession endured long after they stopped seeing each other.
Back in Illinois, Juenger was pestered with doubts about her relationship with Hunter and all of its baggage. Was she foolish to think he might be serious about her? Did Hunter care about her at all? In his letters, he opened up to Juenger and tried to shatter any misconceptions she might have: “I don’t think you have any idea who Hunter S. Thompson is when he drops the role of court jester,” he wrote. “First, I do not live from orgy to orgy, as I might have made you believe. I drink much less than most people think, and I think much more than most people believe. . . . I am basically antisocial.”
All the while, Hunter continued his affair with Ann Frick in Tallahassee.
After a year of wrestling with Hunter, Colonel Evans, who supervised Eglin’s information services and faced the Thompson Problem daily, finally wrote to the base personnel office. “This Airman, although talented, will not be guided by policy or personal advice and guidance. Sometimes his rebel and superior attitude seems to rub off on other airman staff members. He has little consideration for military bearing or dress and seems to dislike the service and want out as soon as possible.”
Colonel Evans was right. Hunter certainly wanted out, but he didn’t want a dishonorable discharge. In his own way, he was proud of his military service and believed his experience was good—in theory at least. “I’m for the draft,” Hunter said late in his life. “I think everybody should be in the military. It civilizes the military.”
In mid-October 1957, as he careened toward a discharge—not fast enough for Colonel Evans—he met with an officer to discuss his situation. Hunter used the opportunity to talk about his religious beliefs and his political philosophy. By his account, the officer listened to this soliloquy and then said, “I don’t know exactly what it is about you, Thompson, and I didn’t understand much of what you said; but I can see at a glance that there’s not much sense in trying to make you either act or think like an airman should. I’ll let you know within two days—twenty-four hours, if possible—how soon you can be discharged.”
By early November, he was on his way out. As he wrote Juenger, “The case of THOMPSON V. THE USAF had come to boiling, bubbling climax. The mule train of military bureaucracy, with the help of a few expertly placed jolts of high-detergent oil, has been rolling in high gear for the last two weeks and, believe it or not, has finally come to a logical conclusion: that being that ‘a square peg cannot exist in a round hole.’”
The honorable discharge became official on November 8, 1957, but Hunter couldn’t leave without a parting shot. On purloined Eglin stationery used for official press releases, Hunter wrote, “An apparently uncontrollable iconoclast, Thompson was discharged today after one of the most hectic and unusual Air Force careers in recent history. According to Captain Munnington Thurd. . . . ‘I almost had a stroke yesterday when I heard he was being given an honorable discharge. It’s terrifying—simply terrifying.’ ”
Hunter sent the mock press release to friends to announce his separation from the Air Force. The release was also printed in the Command Courier.
As Hunter drove through the scrubland of the Panhandle and away from his military career, he was starting his second beginning. His childhood ended in jail. His new beginning came in the military, where he discovered journalism. Now he was out of the service, ready to start again. He could point the car toward St. Louis and Kraig Juenger. But he was wise enough to know that a year on a base paper wouldn’t get him a job at the St. Louis Post-Dispatch. What he wanted was New York, but that was probably even more out of reach than St. Louis. There was always college, but after the freedom he’d discovered as a journalist—even one attached to a branch of the armed forces—the life of a college student wouldn’t be satisfying, even if he could find a college that would accept him.
For now, the pull of home was strong. He headed to Louisville—to his family and to Thanksgiving. Everything would follow from there.