Inside Hemingway's Years as an Esquire Writer
Hemingway helped elevate this up-and-coming magazine into a literary destination—and how writing for Esquire became one of the greatest gigs he ever had.
Ernest Hemingway was many things: an acclaimed writer, a once-in-a-generation talent, a global celebrity, and, according to Esquire founding editor Arnold Gingrich, “one of the best friends this magazine ever had.” Beginning with the magazine’s first issue in October 1933, Hemingway contributed to Esquire for many years, making the up-and-coming publication the home of some of his best-known works, including “The Snows of Kilimanjaro” and the short essay that would later become The Old Man and the Sea. Occasioned by the release of Hemingway, Ken Burns and Lynn Novick’s new PBS documentary, Hemingway has come back into the spotlight, as has his long partnership with Esquire, then an upstart magazine that grew into a literary powerhouse thanks in no small part to Hemingway’s influence.
Ernest Hemingway in 1931
Esquire began as a fashion magazine, flush with advertisements for men’s clothiers, which Gingrich planned to distribute in upscale men’s clothing stores and haberdasheries. Owing to the homophobia and stereotyping of the time, Gingrich feared that only gay men would buy a magazine about fashion, and sought to bulk up Esquire’s pages with stories about the “new leisure” that would result from the New Deal. With the New Deal promising an increased societal emphasis on recreation, Gingrich planned to publish supposedly “manly” stories about sports and outdoor pursuits. He set his sights on Hemingway, an ascendant celebrity novelist and prolific journalist with two acclaimed novels under his belt (The Sun Also Rises and A Farewell to Arms), but also an avid outdoorsman as famed for his hyper-masculine pastimes as for his literature.
In 1932, Hemingway and Gingrich met through a chance encounter at House of Books, a now-defunct New York bookstore owned by Marguerite Cohn and her husband, Henry Louis Cohn (who would later become Hemingway’s first bibliographer). Gingrich wrote to Hemingway soon after, pitching him on the magazine’s vision—and on Hemingway’s essentiality to it.
“It will try to be to the American male what Vogue is to the female,” Gingrich wrote. “It aims to have ample hair on its chest, to say nothing of adequate cojones. Just short of splitting a bowel, I’ll try anything to sell you the idea of being in that first issue. Something about fishing in Florida. Or about hunting. Or about anything you like …. And—I promise—no editing whatever. You write and I print—no monkey business en route to the printers.”
Arnold Gingrich, the founding editor of Esquire.
It was a compelling sales pitch, with just one problem: Gingrich could only pay $250 per story, which didn’t thrill Hemingway, who described his standard fee as “the top rate they have ever paid anybody. This makes them love and appreciate your stuff and realize what a fine writer you are.” For reasons that remain unclear to biographers, Hemingway agreed to accept the low fee, promising to write one piece for each of Gingrich’s first year of quarterly issues. However, he urged Gingrich to keep the deep discount a secret.
“Writers get paid by a certain category—i.e. what they can get—it is a racket controlled by supply and demand,” Hemingway wrote. “I would rather write for nothing if I had any way of living or enough cash otherwise. Because I haven’t I have to keep the category that I have and charge them plenty …. But if you tell anyone I wrote you pieces for 250 it would cost me 2500 a piece.”
Hemingway's Old Typewriter When He Was Writing in Cuba
So began a long and fruitful arrangement between Hemingway and Gingrich, wherein Hemingway submitted “letters” (casual shards of first-person nonfiction) from far-flung corners of the world (like Havana, Key West, Kenya, and Paris), with each letter depicting the locale’s way of life and way of sporting. Hemingway’s first story for Esquire, a “Cuban Letter” titled “Marlin Off the Morro,” appeared in the magazine’s first issue. Esquire proved an instant success—so much so that the original clothing store distribution plan was scrapped on day one. The few issues placed on newsstands sold out so quickly that Gingrich and his colleagues spent the first day of Esquire’s history repossessing store copies of the magazine to replenish the supply at newsstands. Following the success of the inaugural issue, Hemingway convinced Gingrich to raise his fee to twice the going rate; as the magazine’s fortunes increased, so too would Hemingway’s paycheck continue to grow in size.
Hemingway proved to be a backbone of early Esquire in more ways than one. In addition to providing his own writing, he introduced Gingrich to some of the decade’s biggest name-brand writers, including John Dos Passos and Ring Lardner (who appear in the first issue alongside Hemingway), as well as F. Scott Fitzgerald, Ezra Pound, and Theodore Dreiser. As a result, Gingrich became known as “a headhunter of famous authors." Hemingway’s assistance in building the magazine’s literary stable and the sheer volume of his output aided in elevating Esquire to its early prestige and success. Dr. Robert Trogdon, a Hemingway scholar at Kent State University, insists that Hemingway “lent the new magazine a type of legitimacy that would have been difficult to acquire otherwise.”
Hemingway's House in Key West, Florida
But if it seems Esquire got the better end of the deal, think again. Geoffrey Ward, the writer of Hemingway and Burns’ longtime collaborator, points out that Hemingway had engineered his arrangement with Esquire into an extremely cushy gig.
“It was an absolute dream job,” Ward said. “He loved journalism, but he didn’t want to do it full-time. He liked being paid twice the going rate. He loved not being edited at all. He liked not having to write unless he had something to say. He could write about anything he wanted, from fishing to hunting to boating to politics. He could blow off steam in Esquire. Some of his writing for Esquire is simply wonderful.”
Hemingway’s collaboration with Esquire wasn’t just lucrative and low commitment; it was also full of enviable perks. As Mary Dearborn writes in Ernest Hemingway: The Biography, Gingrich sought to sweeten the deal for his star writer by providing swag from the magazine’s advertisers: namely, shoes and clothing. Hemingway promised to “wear out” anything Gingrich sent, but the gifts of high-quality garb fell on a sartorially hopeless subject. As the always-natty Gingrich deadpanned of Hemingway’s trademark style, “The general effect is that of items left over from a rummage sale.” Hemingway also convinced Gingrich to advance him $3,000 against future articles to finance his 38-foot fishing boat, the Pilar, which would go on to influence two of his books: Islands in the Stream and The Old Man and the Sea.
As Gingrich promised in his very first missive to Hemingway, his editorial motto was, “He edits best who edits least.” Dearborn reports that Gingrich held true to his word; he later wrote of his laissez-faire editorial relationship with Hemingway, “We… always operated on the basis that I would make no changes of any kind, but would suggest changes, by wire or telephone, only if impelled to do so by considerations of libel, invasion of privacy, obscenity.” In those early years of their creative partnership, Gingrich and Hemingway corresponded often. Gingrich wrote glowingly of their working relationship in the June 1937 issue: “For the first two years he was... [Esquire’s] most conscientious contributor. He had to send his copy in from all over the world and he never let us down. He more than once chartered planes to reach a point where he could dispatch his piece in time to make a deadline... He was there when we needed him and as long as we needed him. He never needed us.”
Amid their years of collaboration and correspondence, Hemingway and Gingrich struck up a quasi-friendship, which historian James Tobin likens to the bond formed by executives on the golf course: “liking each other but watching for opportunity.” When Hemingway invited Gingrich, an avid fisherman, to join him on a deep sea fishing expedition, tagalong Dos Passos observed, “It was as much fun to see Ernest play an editor as to see him play a marlin. The man never took his fascinated eyes off Old Hem… He would print anything Hemingway cared to let him have at a thousand dollars a whack.”
On another storied fishing trip, it was Gingrich who carried the day. When Gingrich attempted to persuade a stubborn Hemingway to submit a particular story to Esquire, Hemingway proposed a contest to shoot down beer cans. Gingrich, who had never fired a gun, won the contest and the story, later explaining, “I guess he was drunker than I was.”
Hemingway at Sea
Playing his star writer’s games allowed Gingrich to publish Hemingway’s fiction and nonfiction in twenty-eight of the magazine’s first thirty-three issues. Over the course of these issues, Esquire shaped Hemingway as much as he shaped it. In Esquire, Trogdon explains, Hemingway was able to flex his political muscles, writing at length about the rise of fascism in Europe and the Italian invasion of Ethiopia. The Esquire partnership also proved instrumental in cultivating Hemingway’s hyper-masculine persona; as Dearborn writes, “From the start, the Esquire pieces won him a large readership… the ‘letters’ did much to establish him as a hard-living, hard-drinking, fearless, adventurous sort who was living a life most (male) readers wished were their own—for better or worse.”
Esquire also proved to be an adaptable venue where Hemingway could experiment with a new form of journalism. Though it’s commonly agreed that New Journalism arose in publications like Esquire beginning in the 1960s, Ward argues that Hemingway was “the first New journalist,” as his nonfiction writing for Esquire met all the benchmarks of New Journalism: immersive reportage, a stylized literary sensibility, and a subjective bent from the writer. Hemingway’s many “letters” plunged readers into evocative, meticulously reported landscapes, with Hemingway often weaving himself into the first-person narrative as the consummate insider. This was consistent with Hemingway’s broader literary ethos, wherein the line between life and art was often hazy at best.
“He saw the possibilities of nonfiction before many others did,” Trogdon said. “In his own reading, Hemingway did not have a preference between fiction and nonfiction. He enjoyed nonfiction writers and travel writers as much as he enjoyed Tolstoy.”
Hemingway’s collaboration with Esquire was not without friction. Over time, he and Gingrich soured on one another. As Dearborn recounts, Hemingway “believed his own press,” and developed an outsized ego that left him extremely hostile to edits. One afternoon aboard the Pilar, Gingrich was speechless when Hemingway compared himself to Cezanne, saying, “What I can’t get through your Pennsylvania Dutch skill is that you’re not dealing with some little penny-a-liner from the sports department of the Chicago Daily News. You’re asking for changes from a man who has been likened to Cezanne, for bringing ‘a new way of seeing’ into American literature.” Of Hemingway’s sycophantic and transactional approach to relationships, Gingrich later observed, “As long as people around him were worshipping and adoring, why, they were great. The minute they weren’t, there was a tendency to find others who were.”
In 1936, Hemingway retreated from the steady clip of his work for Esquire while traveling extensively and working on his latest novel, writing to Gingrich, “It is practically a sin against the holy ghost for me to interrupt writing the novel at this point to write a [journalistic] piece or a [short] story. If I don’t give it every bit of juice I have… I’m a son of a bitch… I feel goddamned bad about this Arnold... I think of you as the best and most loyal friend I have and the one guy who knows what I am trying to do. By staying out of the magazine now I am probably fucking up my commercial career as badly as I fucked up my critical status (the hell with it) by staying in it. But I haven’t any choice as long as I am working on this.”
The novel in question, To Have and Have Not, was a fictionalized account of the splintered marriage between millionaire Pan Am executive G. Grant Mason Jr. and socialite / sportswoman Jane Kendall Mason. Largely considered Hemingway’s worst novel, To Have and Have Not was cobbled together from two short stories: “The Tradesman Returns,” which ran in Esquire, and “One Trip Across,” which was published in Cosmopolitan. While living in Havana during the 1930s, Hemingway carried out an on-again, off-again affair with Mrs. Mason for over four years. During a trip to visit Hemingway in the Bahamas in 1936, Gingrich also struck up an affair with Mason, who sailed aboard the Pilar with Hemingway and his entourage. According to Gingrich, a territorial Hemingway muttered, “Goddamn editor comes down to Bimini and sees a blonde, and hasn’t been the same since.” A jilted Hemingway would later seek to punish Mason in “The Short Happy Life of Francis Macomber,” using her as inspiration for the cruel femme fatale Margot Macomber.
Hemingway in the Bahamas with his three sons, circa 1935
Gingrich was alarmed by the novel’s verisimilitude and urged Hemingway to dial back the real-life parallels to avoid a libel suit, but Hemingway refused, and the argument ended any sense of bonhomie between them. Following the conflict, Hemingway published three further works of fiction in Esquire, then severed the relationship altogether. In 1955, after an intermittent two-decade affair, Gingrich married Mason, to whom he remained wedded until his death in 1976. Upon hearing the news of their marriage, Hemingway reportedly bellowed, “That shit!” When asked by one of his sons why he stopped writing for Gingrich, Hemingway said only that they had “disagreed about a blonde.”
Though their friendship ended, the work remains. In Gingrich, Hemingway found a permissive editorial partner whose willingness to sanction (and bankroll) his every impulse ultimately cemented his legend. In Hemingway, Gingrich found the man he once called the magazine’s “principal asset”: an international celebrity and powerhouse writer who vaulted the magazine into the stratosphere, enabling it to sell over ten million copies during the height of the Great Depression. Following Hemingway’s death by suicide in 1961, Gingrich dedicated a significant portion of Esquire real estate to memorializing Hemingway’s life and critically evaluating his body of work, publishing semi-regular coverage of the late Hemingway until his retirement in 1974.
Sometimes friends, occasionally rivals, always collaborators, together Hemingway and Gingrich produced some of the most remarkable literary journalism of the twentieth century, which went on to shape what the journalism of the future could do and be. Gingrich argued that Hemingway “never needed us,” but it’s difficult to imagine Hemingway’s illustrious career without Esquire, the literary workshop where he could tinker with ambitious forms, expect a steady paycheck, and construct his towering legacy as a man of letters. Long after his death, Hemingway’s titanic influence continues to loom large in the pages of Esquire, and in magazines around the world. Gingrich said it best in the June 1967 issue, where he remembered his late friend thusly: “There are people about whom anything new is news. Ernest Hemingway dead is still far more newsworthy than almost any writer you can think of who is still living.”
This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.