At any rate, while I was in New York City I ran into a lad who offered to take my book (the finished part) to a friend of his at Appleton-Century-Crofts. I don’t know what this means, but I sense the vague possibility of an advance. To secure such a thing, there is no doubt in my mind that I’d run the seventy miles from here to Manhattan at top speed in the dead of night with the manuscript strapped to my back.
I want you to know, however, that if these Appleton people show any interest at all in the book, I shall call you immediately. You were very kind to take an interest in my book, and the only reason I haven’t delivered it to you by now is this wretched, degrading, nerve-shattering poverty.
At any rate, if this wino turns out to have no friends at Appleton, or if they mock me and drive me from the building, and if I can sell enough old Ballantine ale bottles to keep me alive until I finish the book, I shall get it to you as soon as possible. If it’s not finished by Christmas, I may give up the ghost and get a job with the Salvation Army.
Until then, I remain, grimly:
Hunter S. Thompson
TO PUERTO RICO BOWLING NEWS:
Desperate for work in the Caribbean, Thompson applied for a sportswriting position at the Puerto Rico Bowling News. Philip Kramer, the editor and publisher, asked Thompson to send more information about himself.
November 25, 1959
Otisville, New York
Gentlemen,
Are you looking for a bowling writer, or a sportswriter? Your ad was a little confusing on this point.
If you’re looking for a sportswriter, I’ll be available on or about January first.
The enclosed clippings aren’t quite up to date, but they should give you an idea of who I am, and how I write. During the past two years I’ve worked as an editorial trainee for Time magazine, and as a reporter for an upstate New York daily. At the moment, I’m working on a novel that should be finished by the first of the year.
It’s a big jump from New York to Puerto Rico, but if life down there is as warm and easy as rumor would have us believe, then it might be worth the trip.
At any rate, please return my clippings when you answer the letter.
Sincerely,
Hunter S. Thompson
TO PHILIP KRAMER, PUERTO RICO BOWLING NEWS:
Not wanting to miss a chance to move to Puerto Rico, Thompson lied about his age in a successful maneuver to land a job with El Sportivo, a new English-language Puerto Rican sports weekly focused on bowling.
December 14, 1959
Otisville, New York
Dear Mr. Kramer:
You said you were leaving for New York in seven days and it took four of those for your letter to get to Otisville. I will make this brief, and try to get it in the morning mail, hoping it will get there before you leave.
I am single, an Air Force veteran, twenty-five, and definitely interested in talking with you about this job. I’ve been sports editor of two Florida weeklies, one Pennsylvania daily, and a command newspaper in the Air Force. More recently, I’ve worked as an editorial trainee for Time magazine, and as a general reporter for a New York (State) daily. For the past nine months I’ve been writing a novel, most of which is now awaiting judgment at a New York publishing house.
You apparently misunderstood my remark about life being “easy” down there. Perhaps I should have said “warm and pleasant,” or something equally inane. In Florida, I was sports editor of two competing papers at the same time, sometimes working twenty hours a day—and I enjoyed it thoroughly. All I ask of any job is that it be challenging, satisfying and at least financially rewarding enough to keep me out of the bread-line.
I’d have to find out a little more about your plans before I could take any definite steps, but I’ll wait till I see you in New York before I ask any questions. […]
Sincerely,
Hunter S. Thompson
TO ROBERT BONE:
Shortly after Thompson was fired from the Middletown Daily Record reporter-photographer Bone also left to find a job in Manhattan. He wound up at the San Juan Star. By 1961 he was working at a financial magazine in Rio de Janeiro.
December 14, 1959
Otisville, New York
Robert:
Just finished reading your article in the Record (“Statehood or Status Quo”) and found it distinctly inferior to the report of the Red hearings. Who wrote that other one for you?
Pardon that jab. It’s not the reason for this letter, but I figured you needed something to make up for all those compliments I tossed off in my last communication. Incidentally, the copy of the Star (front page editorial) that you sent up here was one hell of an improvement over the first one I saw. Looks like Kennedy might have shaken the Rotary Club influence.
But now to the point. There’s a slim chance that I might hop down that way sometime soon, but I’m going to need a bit of information from you before I commit myself. A guy named Philip Kramer, editor-publisher of something called the Puerto Rico Bowling News, says he’s starting a new monthly sports magazine down there (“similar in style to that of Sports Illustrated”) and he’s looking for sportswriters. He’s located in Roosevelt, Puerto Rico, which I can’t even find on the map. If you can answer the following questions for me and get the answers back by return mail, I will appreciate it no end—and may even stand you a few drinks if and when I get down there. At any rate, I have to see Kramer in New York next week and I hope you can get your reply to me before then. Send it c/o Murphy, 69 E. 4th St., Manhattan.
Here we go:
1) where is Roosevelt? what sort of place is it?
2) do you know anything about Kramer? his letter sounds like it was written by either a fanatic or a crack-pot.
3) from what you know of the cost of living down there, what would be the minimum salary you’d accept if you were in my shoes?
4) have you heard anything about this proposed magazine? it would have to have a hell of a lot of money behind it to be anything but a pipedream, and I don’t want to come down there for something that will fold in a week.
5) do you honestly like Puerto Rico? Also, what are the main drawbacks and/or advantages?
If you can think of any other pertinent information along these lines, by all means send it along. And once again, do not send your reply to Otisville. If you write immediately, and send it to New York, it should arrive about the same time Kramer does. And for god’s sake, don’t mention this to Kennedy (or anyone else at the Star, for that matter). If Kramer ever got wind of my dealings with the Star, he’d avoid me like the plague. As it is, I may have a chance of duping him into thinking I’m normal. The reason I’m writing you is that I don’t want him to dupe me. So … thanks for any help you can give me. May see you sometime soon.
Cheers: H
TO MARK ETHRIDGE, LOUISVILLE COURIER-JOURNAL:
Just before departing for Puerto Rico, Thompson had pitched a story idea to the editor of the Louisville Courier-Journal. Ethridge rejected the idea but asked Thompson to become his newspaper’s Caribbean stringer. Thompson was thrilled at the prospect of seeing his byline in his hometown paper.
December 28, 1959
New York City
Dear Mr. Ethridge:
Last Derby day, while a whiskey-soaked throng of some 100,000 struggled to its feet for the annual Churchill Downs rendition of “My Old Kentucky Home,” six expatriate Louisvillians stood in front of a television set in a small Greenwich Village bar. And that night, there was a “Derby Party” on West 78th Street, about a hundred yards from the thug-infested woodlands of Central Park.
If this interests you, then read on. I think I’ve stumbled on a decent idea for a story for the Courier-Journal: the community of Louisville expatriates in Manhattan. No other city in the United States—and Paul Semonin and I have checked this out thoroughly—seems to have such a conspicuous and close-knit representation here. Offhand, I can think of nineteen people, all roughly the same age (ten boys and nine girls), who have either worked
or lived here within the past year. I cite, as prominent examples, Paul and Debbie Newman at the Art Students’ League, David Bibb publishing IVY magazine from an office in the Biltmore Hotel, Floyd Smith at Columbia, Tad Minnish and Buddy Hayes among the Beatnik set in Greenwich Village, Sally Spaulding working for Time, Olivia Smith working for an executive personnel agency on the East Side, Henry Eichelburger at an Army Intelligence (Russian Language) School, and Ralston Steenrod wheeling and dealing in the dark caverns of Wall Street and the Financial District.
At any rate, this should give you an idea of what I’m shooting at. These people are here for different reasons, most of them move in different circles, and all of them have their own reasons for leaving Louisville (some of them, for that matter, intend to return; and some don’t). Actually, the only thing they have in common is that they comprise a sort of “Louisville colony” here in the middle of New York. I think it’s a good story and I don’t think you should pass it by.
As for terms, I leave that to you. I think you’ll be fair. I can offer either a single shot (Louisville Expatriates in New York) or a series of contrasting interviews—with photographs of different apartments and pastimes. Naturally, I’d prefer whatever arrangement would bring me the most money. […]
Sincerely,
Hunter S. Thompson
c/o Dick Murphy
69 E. 4th Street
Manhattan
William J. Kennedy (right) with (left to right) Rear Admiral Daniel Gallery, commander of U.S. Navy base in Puerto Rico; Vice President Richard Nixon; and Luis Munoz Marin, governor of Puerto Rico. (COURTESY OF HST COLLECTION)
Thompson earned money while in Puerto Rico working as a male model. (PHOTO BY PAUL SEMONIN; COURTESY OF HST COLLECTION)
While in Puerto Rico, Thompson began taking photography seriously, selling many of his prints—such as this one—to San Juan travel magazines. (PHOTO BY HUNTER S. THOMPSON; COURTESY OF HST COLLECTION)
Sandy Conklin—soon to be Thompson’s wife—moved to Puerto Rico to live with him. (PHOTO BY HUNTER S. THOMPSON; COURTESY OF HST COLLECTION)
Sandy Conklin, Hunter S. Thompson, and Paul Semonin marooned in Bermuda. COURTESY OF HST COLLECTION)
1. Laurie Hosford, who attended the University of Florida at Tallahassee while Thompson was stationed at nearby Eglin, often accompanied Thompson on double dates.
2. Bradley Smith, Escape to the West Indies (New York, 1957).
3. Pilar was a Doberman pinscher puppy Thompson had purchased the day before he was fired by the Record.
4. A small town between Jacksonville and Orlando, Florida.
5. Peyton is the main character in William Styron’s Lie Down in Darkness.
6. Arthur Hays Sulzberger, owner of The New York Times.
7. Jo was Roger Richard’s wife.
8. The good story was “The Cotton Candy Heart,” the useless one “The Almost Working Artist.” Both remain unpublished.
9. Excerpts from the novel, “Prince Jellyfish,” which was never published in its entirely, did appear in Songs of the Doomed.
10. June Christy was a popular Chicago jazz singer in the 1940s and 1950s.
11. See epigraph on page xv.
12. Bill Forbes was Thompson’s friend and neighbor at 57 Perry Street.
13. Thompson had included on his résumé that he had been fired from the Middletown Daily Record for kicking a candy machine.
14. Styron’s home was in Roxbury, Connecticut.
15. “Come join the Pepsi Generation” was a popular advertising slogan of the late 1950s.
16. Avare, a dimwitted publisher, was the lead character in Thompson’s one-act play, The Dry Rot of American Journalism.
1960
NEW LIFE IN THE TROPICS … NAKED, CRAZY, AND RICH ON LUQUILLO BEACH … THE BOWLING DISASTER, THE BEATING, THE BEAUTY, AND THE NEW YORK HERALD TRIBUNE … ESCAPE FROM PUERTO RICO, DEPORTED FROM BERMUDA … LONG RUN TO SAN FRANCISCO, LONG CHAIN OF FAILURE … BAD NEWS FOR THE SWINE FAMILY …
All manner of fearful deviations thrived in that muggy air. A legion of pederasts wandered the narrow sidewalks of the Old City of San Juan, giggling at every crotch. The bars, the beaches, and even the best sections of town literally crawled with rapists and crab dykes and muggers and people with no sex or sanity at all. They lurked in the shadows and foamed through the streets, grasping and grabbing like crazed shoplifters driven mad by the Tropic Rot!
—Hunter S. Thompson,
“The Rum Diary” (unpublished novel)
TO HOME (VIRGINIA THOMPSON):
Just after the New Year Thompson left New York for San Juan, Puerto Rico. His plan was to make enough money working at El Sportivo (aka Bowling News) and writing free-lance pieces to finance a new novel set in the Caribbean.
January 14, 1960
San Juan, Puerto Rico
Dear Home:
Damn, how far away I seem—even to me, who is used to being far away. I trust you got my card, and hope this letter will fill you in a bit more.
Still, oddly enough, very little concrete news to report. This could be either the best or (no, not really the worst, because even at its worst it couldn’t be too bad) perhaps the most outlandish thing I have ever done. It all depends on how this magazine goes. If it folds, I will be out on a limb; but if it goes, I will be in on a very lucrative ground floor. As of now, I’m very definitely the “number one boy.” Kramer told me tonight that I didn’t have to worry about the trial period as long as I kept turning in things like the two stories I did this week. The original plan was for me to work for three months on this ridiculously low salary, and then—if I “worked out”—I would get a fairly sizable raise and a “permanent writer” status. Tonight he said I probably wouldn’t have to wait that long. So things are going as well as they could be under any circumstances.
San Juan is a strange combination of old and new. The cost of living here is incredible, yet some Puerto Ricans live on ten dollars a week. Very definitely a dual economy. One night I am having dinner at the Caribe Hilton, the next at a native bar on a street ten feet wide. Bob Bone—ex-compatriot on the Daily Record—has been a tremendous help. He’s working for the Star, the new English-language daily. Kramer is decent, but a little crazy; and the job is so easy and pleasant that I don’t see how it can last. I have no hours, no office, one story assignment a week, and I am 98% on my own all the time. The other writer—hired in New York at the same time I was—is a good lad, but not much of a writer. Perhaps this accounts for Kramer’s enthusiasm for me. Whatever it is, I am not worrying at the moment. I’ve sent off a few queries for free-lance assignments, and if I get those my financial situation should take a definite turn for the better.
The main problem here is clothes. Everything is frightfully expensive and no one on the island can tell me where to get a cord suit. All suits are $60 and $70 and I know they have them at Rhodes1 for $25. Would it be possible for you to buy one there and send it to me? Make it my birthday present. All I have to my name now is a very ratty and well-worn tan cord coat that I got at Lad-a-Dad three years ago—too small and a nasty frayed collar. I will send you my measurements on a separate sheet and if you can get the suit for me I will be most happy. Or else I will have to order it from Brooks Brothers or something like that in New York.
[Paul] Semonin should be down here in a few weeks and Kramer said he might want to hire him as a staff artist. Hope so—that would be a good deal. I meant to tell Paul to come by the house while he was in Louisville. He’s a real champion, but I don’t think you know him very well.
Thanks again for the plane fare. You-all have been wonderful in these periodic financial emergencies. No word yet on the novel, but I’ll let you know as soon as I hear something.
All in all, I think this was a wise move. Of course, except for the Jaguar money, that fiasco in Middletown turned out to be a good thing, too. It took a thing like that to actually get me writing.
Before I go, let me give you a typical day. Rise at ten, go
to La Rada (very fashionable) Hotel for lunch and interview with owner-chef, spend afternoon on beach with some people from Philadelphia, out to Kramer’s house for conference on La Rada chef story, back to quarters to write story and few letters. Time out after Kramer conference to eat dinner with Douglas, the other writer. Then to bed and up again for another grueling day.
That’s about it. I’ll write again when I know more. In the meantime, let me hear from the homestead.
Love, Hunter
Measurements: size 44 coat; shirt size 15 (neck) 35 (sleeve); pants size 34 waist, don’t worry about length; I will find a tailor here and have him put cuffs on the things.
I want a grey cord suit—same color Davison has. If possible, send me his now and get him a new one with the money you would have spent for mine. I don’t necessarily need a new suit; I just need something to wear. The same coat everyday gets a little tedious. Yes, that’s an excellent idea. Send me Davison’s suit as soon as possible and tell him I’ll pay him back by putting him up during spring vacation. On the other hand, that suit of his may be in pretty bad shape by this time. If so, try to get me a new one. If not, send it on. And if you can’t get hold of a cord suit this time of year, thanks anyway. It’s a queer request, but I just hate to pay $60 for a suit I don’t like as well as a $25 cord. And if the grey cord isn’t available, get me an olive-drab wash-and-wear. Try also to make whatever you send me wash-and-wear. Laundry here is quite a problem. […]
Love, Hunter
TO DISTRIBUTION MANAGER, BROWN-WILLIAMSON TOBACCO COMPANY:
Thompson started smoking Kools while a sophomore at Louisville Male High School. He would smoke no other cigarette until 1962, when he discovered Dunhills in Rio de Janeiro.
January 15, 1960
164 Ave. Flamboyanes
Hyde Park, Puerto Rico
Distribution Manager
Brown-Williamson Tobacco Co.