Hemingway believed that insults could be crushed and arguments settled, gangland fashion, with menacing threats or physical violence. His friends agreed that he could be violent when crossed and angered. His sidekick Toby Bruce said he ‘could be as mean as a striped-assed ape’; the photographer Robert Capa stated, ‘Papa can be more severe than God on a rough day when the whole human race is misbehaving’; and General Buck Lanham insisted, ‘When Hemingway was nasty he qualified as The King of All Nasties.’ The huge and powerful Hemingway was always dangerous. When the timid, weak-eyed James Joyce got into drunken arguments with strangers he could scarcely see, he’d summon his strongman and bodyguard, and declare, ‘Deal with him, Hemingway! Deal with him!’

The thin-skinned, quick-tempered Hemingway was easily provoked. When Don Wright, one of the bachelor tenants in their Chicago flat, was having an affair with his friend’s wife Hemingway wanted to punch him. When his satire of Chard Powers Smith in his story ‘Mr. and Mrs. Elliott’ provoked an abusive letter, Hemingway threatened to hit him. When Arthur Moss, the editor of the Boulevardier, had to cut obscenities from his essay, Hemingway threatened to knock his block off. After a drunken Polish engineer on a ship to Europe called him a ‘capitalist, bourgeois pig,’ Hemingway challenged him to a duel on deck with pistols, but the engineer failed to appear. Women were not immune from his fury. When his fourth wife, Mary, called him a son of a bitch, he warned her, ‘Most people would be running if they called me that.’

He carried out his threats in physical combat with Harold Loeb, who aroused his jealousy by having an affair with Duff Twysden in Spain; with Robert McAlmon, who called him a fairy; with Max Eastman who said he had no hair on his chest; and with Wallace Stevens, who publicly insulted him and made his sister cry. But he never went a few rounds with his arch-enemy Gertrude Stein.

Hemingway grew up in the genteel suburb of Oak Park. But during his teenage and young adult years Chicago had a worldwide — and to him exciting — reputation for violence, corruption and crime. In 1910, for example, the city had 7,500 legal saloons, and 192 houses of prostitution with 189 madames and 1,012 inmates. The average age of a prostitute was twenty-three and her professional life lasted for about five years. One gang boss earned as much as $50,000 a month for eight years.

The mobster Johnny Torrio had a saloon on the first floor of his Four Deuces club, offices and a horse-betting room on the second floor, a gambling den on the third floor, and a two-dollar whorehouse on the top floor. According to Herbert Asbury’s The Gangs of Chicago, Torrio ‘bought and sold women, conferred with the managers of his brothels and gambling dens, issued instructions to his rum-runners and bootleggers, arranged for the corruption of police and city officials, and sent his 750 gunmen out to slaughter rival gangsters.’ He gave liberally to political campaign funds, and bought attorneys and judges, prohibition and law enforcement agents, county officials and politicians. The corruption unleashed rampant crime in the city. Bandits who didn’t even bother to wear masks robbed banks all over Chicago. Robbers who failed to survive were awarded lavish gangland funerals with oceans of flowers and long processions of limousines.

Alphonse “Scarface” Capone, the most notorious Chicago gangster, was born in 1899, the same year as Hemingway. He made money by corrupting labour unions, pimps and prostitution, gambling and extortion, racketeering and bootlegging. Capone ruled by leaden clubs and tommy-guns, and held power by inciting constant gang wars and frequently massacring his enemies. But he also had a Gatsby-like obsession with expensive haberdashery. His biographer Laurence Bergreen writes that ‘in 1927 and 1928 he had bought himself twenty-three suits and three topcoats,’ which cost $3,715. ‘The shirts, which went for $18 to $30, he bought literally by the dozen, as he did the neckties, the collars and the handkerchiefs.’
Though Capone had an ironclad alibi, he was supposed to have organized the St. Valentine’s Day massacre. On February 14, 1929 seven men, Asbury writes, ‘waiting at the garage for a truckload of booze . . . were disarmed and lined up against the wall by three gangsters wearing police uniforms. Then two other men, in plain clothing, stepped forward and raked the line with machine-guns.’ Some Like It Hot (1959) parodied this scene when Jack Lemmon and Tony Curtis accidentally witness George Raft’s gangland massacre and have to disguise themselves as women to escape retribution. When Capone was convicted of carrying a concealed weapon, he ‘continued to transact his business from the Eastern Penitentiary [in Philadelphia]. He was given a private cell, allowed to make long-distance calls, and to use the Warden’s office for conferences with his lawyers.’

Like the great masculine writers — Joseph Conrad, André Malraux and George Orwell — Hemingway did not go to college but learned from practical experience in the real world, from reporting gang wars in Kansas City and Chicago and international wars in Europe. As Herman Melville said, ‘A whale ship was my Yale College and my Harvard.’ The young Hemingway first worked, from October 1917 through April 1918, as a journalist on the Kansas City Star. He then served in the First World War with the Red Cross and was seriously wounded in Italy. After returning from Europe he spent more than a year in Chicago in the early 1920s working on the Co-operative Commonwealth magazine. At a time when gangsters flourished during Prohibition (1920-33), he published many articles about crime in Chicago in the Toronto Star Weekly.

Hemingway’s time in Kansas City was his first break from the conventional values of his family in Oak Park and from the church’s tedious preaching about personal cleanliness, filial obedience, sobriety, piety and chastity. In Missouri he developed a lifelong fascination with whores and horror of venereal disease. He declared, ‘I never thought Chicago was a tough place,’ but allowed, in a characteristic understatement, that Kansas City ‘was a little rough.’

All discussions of his time in Kansas City, beginning with Charles Fenton’s The Apprenticeship of Ernest Hemingway (1954), emphasize how he learned to write clearly and concisely from the Star’s style sheet. But the gangsters he wrote about were even more important. Just as Upton Sinclair’s The Jungle (1906) had exposed the exploitation of immigrant workers (one of whom gets ground up and packaged after falling into a machine) in the Chicago meat-packing industry, so the vividly morbid newspaper articles by Hemingway and other reporters exposed the unchecked crime in those Midwestern cities.

Hemingway’s exact, crisp and violent ‘Battle of Raid Squads’, published in Kansas City on January 6, 1918, described the danger of trigger-happy officials, as well as of the real gangsters, in urban battles:

John M. Tully and Albert Raithel, revenue officers from St. Louis, may die, and two city detectives narrowly escaped injury as a result of a revolver battle yesterday through a case of mistaken identity. Tully and Raithel had gone to raid a house at 2743 Mercier Street, reported to be a rendezvous for drug users. Edward Kritser and Paul Conrad, city detectives, arrived a few minutes later on the same mission. Each party of officers mistook the other for drug peddlers.

Tully was shot in the right leg, left arm and lower abdomen. Raithel was wounded in the abdomen and left wrist. Both will recover. The two detectives were uninjured, but both had bullet holes through their clothing.

In ‘At the End of the Ambulance Run’, which appeared in the Star on January 20, 1918, Hemingway revealed his taste for gory details and use of inside information (which he later called ‘the true gen’), and described the different ways of inflicting damage in different parts of the city: ‘It’s razor wounds in the African belt and slugging in the wet [liquor] block. In Little Italy they prefer the sawed-off shotgun. We can almost tell what part of the city a man is from just by seeing how they did him up.’

Two years later, in his post-war Toronto Star Weekly stories about Chicago, the seasoned veteran continued to concentrate on violent gangsters. In ‘Rum-Running’ (June 5, 1920), he reported the unrestrained liquor
smuggling during Prohibition: ‘Canadian whiskey can be bought by the case from bootleggers in almost all of the Michigan border towns for one hundred and twenty dollars a case.’ ‘Wild West: Chicago’ (November 6, 1920) compared the escalating murders in Chicago — eerily similar to those in that city today — to the lawless shootouts on the old frontier:

in the city of Chicago during the present year from January to November there have been one hundred and fifty killings . . . . By including the police bag, it would be pretty safe to say they kill somebody every day in Chicago . . . . So there is murder, drink and gambling in the new Wild West just as in the old.

The professional murderers in Chicago were so highly regarded, Hemingway explained in ‘Plain and Fancy Killings, $400 Up’ (December 11, 1920), that ‘Gunmen from the United States are being imported to do killings in Ireland’ during the war of independence. ‘The price for a simple killing, such as a marked policeman or member of the ‘Black and Tans,’ is four hundred dollars.’

Finally, in ‘Ballot Bullets’ (May 28, 1921) — whose title would be echoed in the Humphrey Bogart and Edward G. Robinson movie Bullets or Ballots (1936) — Hemingway connected politics with violent death and narrated the incident from the victim’s point of view, as he would later do when describing the wounded lion in ‘The Short Happy Life of Francis Macomber’:

Anthony D’Andrea, pale and spectacled, defeated candidate for alderman in the 19th Ward, Chicago, stepped out of the closed car in front of his residence and, holding an automatic pistol in his hand, backed gingerly up the steps.

Reaching back with his left hand to press the door bell, he was blinded by two red jets of flame from the window of the next apartment, heard a terrific roar and felt himself clouted sickeningly in the body with the shock of the slugs from the sawed-off shotgun. . . . It’s all part of the unfinished story of the gunmen’s political war that is raging in Chicago at present.

Hemingway expressed his fascination with gangsters in his fiction, and evoked the atmosphere of Kansas City during the last year of the war in two minor short stories and an interchapter of In Our Time. In ‘A Pursuit Race’ (1927), a staggered bike race, an advance man for a burlesque show breaks down with drink and drugs. Hemingway wrote that ‘It was very cold in Kansas City’ and that the hopeless anti-hero ‘did not like Kansas City,’ but ‘knew there were good cures in Kansas City’ for drug addicts.

The ironically titled ‘God Rest You Merry, Gentlemen’ (1933) begins with a far-fetched comparison, ‘In those days . . . Kansas City was very like Constantinople,’ and also mentions the Woolf Brothers’ saloon and the city hospital. In this Christmas Day story, an incompetent doctor is unable to deal with a religious fanatic’s attempt to castrate himself. Hemingway may have been thinking of the two most famous castrati. The third-century theologian Origen, slavishly following Matthew 19:12 — ‘there be eunuchs, which made themselves eunuchs for the kingdom of heaven’s sake’ — castrated himself for the love of God. Abelard, the medieval French philosopher, was castrated by the uncle of Héloïse for secretly marrying her. In The Sun Also Rises Jake Barnes’s penis has been shot off in the war. In this story the would-be castrator amputates his own penis. But both mutilated men still have sexual feelings.

Interchapter VIII, based on an incident that took place in Kansas City on November 19, 1917, subtly connects urban violence with war and is related to Hemingway’s news story of the gun fight between revenue agents and detectives. In this taut vignette a policeman, Jimmy Boyle, kills two Hungarians who have robbed a cigar store at two o’clock in the morning. His partner, Drevitts, fears there will be trouble, but he is reassured by the murderer who insists there will be no difficulty because the victims were crooks and ‘wops.’ Since all ‘wops’ are crooks their deaths don’t matter. Boyle claims ‘he can tell wops a mile off.’ His false identification, which reflects the racial hostility between Irish and Italian immigrants, will be accepted in court to justify the deaths of the Hungarians.

On April 15, 1921, Hemingway wrote to his father from Chicago: ‘They hanged Cardinella and Cosmano and some other Wop killer today . . . . Cardinella is a good man to swing I guess. Passed the County Jail this morning and there was a big crowd standing outside waiting for the event.’ Sam Cardinella — the forty-one-year-old mobster, extortionist and leader of the Black Hand gang — was executed for murdering a saloonkeeper. When Cardinella refused to walk to the gallows, he was strapped to a chair, carried to the scaffold and hanged in his chair. When the jailers took his body to an ambulance (not a hearse) hired by his family, they found medical equipment, a nurse and a doctor who hoped to revive the corpse.

Hemingway’s version, interchapter XV from In Our Time, takes place in the corridor of the county jail. One of the condemned men wraps a blanket around his head in an infantile attempt to escape reality. The guards carry Cardinella, accompanied by two priests who mutter meaningless words—another instance of unreality. The terrified prisoner loses control of his sphincter muscle and the disgusted guards, one of them wearing an incongruous derby hat, strap him into a chair. The agile priest skips back onto the scaffolding just before the drop falls. Hemingway realistically described the callousness of the guards, the futility of the priests and the cowardice of the prisoner, who responds to the injunction to ‘Be a man’ by emptying his bowels before he is ‘jerked to Jesus.’

Hemingway’s influential story ‘The Killers’ (1927) is based on the comical-sinister gangsters of Al Capone’s Chicago. Max and Al turn up in a diner, converted from a saloon during Prohibition, to murder a heavyweight boxer. Ole Andreson had agreed to throw a fight but betrayed the gamblers who backed his opponent. The suspense builds up as time passes, threats are made, motives are slowly revealed and Ole fails to appear for dinner at his customary time. In the story, which reads like a screenplay, the killers, passively awaiting the arrival of their victim, taunt and intimidate the workers in the diner with a series of insults that require immediate assent:

‘You’re a pretty bright boy, aren’t you?’
‘Sure,’ said George.
‘Well, you’re not,’ said the other little man. ‘Is he, Al?’
‘He’s dumb.’

The gangsters convey their indifferent, immoral but highly professional attitude — ‘We’re killing him for a friend. Just to oblige a friend’ — which astonishes Nick Adams but is passively accepted by the victim. The two main events in the story, the prizefight and the murder, are left out. The theme, Nick’s discovery of evil and death, is also conveyed obliquely when he goes to warn Ole. The boxer stoically, if not heroically, confronts his fate and rolls over toward the wall: ‘There isn’t anything I can do about it. . . . I’m through with all that running around.’

Nick moves from fear to compassion to disillusionment and realizes things are not what they appear to be: the clock is twenty minutes fast, the lunch-room serves dinner, the corrupt-honest fighter is strangely indifferent, Mrs. Hirsch is actually Mrs. Bell and Ole’s friends are much more frightened than he is. The men in the diner are confused and obedient, Andreson is fatalistic and resigned. The gangsters boldly announce their intention to defy the law and murder the boxer, but do not hunt him down in his boarding house. Though the murderers don’t kill Ole, they merely delay the inevitable and will surely come back to finish the job. The boxer, tired of running, awaits his inevitable fate and doesn’t take his last chance to escape. ‘The Killers’ portrays Hemingway’s recurrent theme of The Undefeated and suggests that pity can be earned only by men who never demand it.

One film critic maintained that gangsters did not ‘know how they were supposed to behave. So Hollywood taught them.’ But Hemingway taught Hollywood. The gangsters of Kansas City and Chicago not only sparked his lifelong taste for violence, but also inspired his portrayal of the criminals that was adopted by movies in the 1930s. The menacing wisecracks, the sense of immediate experience and sharp cinematic scenes influenced the portrayal of underworld characters in films like Robinson’s Little Caesar (1930) and James Cagney’s Public Enemy (1931).

Hemingway, who emphasized the dramatic and visual aspects of gangsters, actually created the natty dress and unrestrained violence of stereotyped movie mobsters. One of the murderers in ‘The Killers’ ‘wore a derby hat and a black overcoat buttoned across the chest. His face was small and white and he had tight lips. He wore a silk muffler and gloves . . . [They] ate with their gloves on . . . [and] were dressed like twins. Both wore overcoats too tight for them . . . . The cut-off barrels of the shotgun made a slight bulge under the waist.’ This precise description clearly foreshadows Bogart’s smart attire in all his gangster roles from the early 1930s to ‘Gloves’ Donahue in All Through the Night (1942). As Bogart says in Across the Pacific of the Japanese villains who are trying to hide their weapons, ‘tight clothes don’t go with guns.’

Emphasizing the theatrical element, Hemingway compares one of the killers, giving orders to his captives, to a member of a vaudeville team and to ‘a photographer arranging for a group picture.’ The murderer tells George, ‘Ever go to the movies? . . . You ought to go to the movies more. The movies are fine for a bright boy like you.’ The detective in Hemingway’s ‘The Gambler, the Nun, and the Radio’ warns the wounded Mexican about confusing art and life: ‘Listen. This isn’t Chicago. You’re not a gangster. You don’t have to act like a moving picture. It’s all right to tell who shot you.’

Hemingway’s first-hand experience with gangsters encouraged his propensity to violence and attraction to violent themes in his fiction. His portrayal of criminals in a sceptical, stoical and belligerently masculine style, with speech and gestures cut down to a minimum, tapped into the Hollywood consciousness that recreated his laconic gangsters and doomed tough guys. There was a volatile connection throughout his life between the gangsters he wrote about while still in his impressionable teens, his passion for danger in war, boxing, bullfighting and big-game hunting, and his brain-splashed suicide.


Jeffrey Meyers, FRSL, has published Painting and the Novel, The Enemy: A Biography of Wyndham Lewis, Impressionist Quartet, Modigliani: A Life and The Mystery of the Real, correspondence with Alex Colville (2016).

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