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article number 254
article date 07-23-2013
copyright 2013 by Author else SaltOfAmerica
The Gangs of Chicago … 1920’s
by Fredrick Lewis Allen

From the 1931 book, Only Yesterday.

In 1920, when prohibition was very young, Johnny Torrio of Chicago had an inspiration. Torrio was a formidable figure in the Chicago underworld. He had discovered that there was big money in the newly outlawed liquor business. He was fired with the hope of getting control of the dispensation of booze to the whole city of Chicago.

At the moment there was a great deal too much competition; but possibly a well-disciplined gang of men handy with their fists and their guns could take care of that, by intimidating rival bootleggers and persuading speakeasy proprietors that life might not be wholly comfortable for them unless they bought Torrio liquor. What Torrio needed was a lieutenant who could mobilize and lead his shock troops.

Being a graduate of the notorious Five Points gang in New York and a disciple of such genial fellows as Lefty Louie and Gyp the Blood (he himself had been questioned about the murder of Herman Rosenthal in the famous Becker case in 1912), he naturally turned to his alma mater for his man.

He picked for the job a bullet-headed twenty-three-year-old Neapolitan roughneck of the Five Points gang, and offered him a generous income and half the profits of the bootleg trade if he would come to Chicago and take care of the competition. The young hoodlum came, established himself at Torrio’s gambling-place, the Four Deuces, opened by way of plausible stage setting an innocent-looking office which contained among its properties a family Bible, and had a set of business cards printed:

Second Hand Furniture Dealer, 2220 South Wabash Avenue

Al Capone.

Torrio had guessed right—in fact, he had guessed right three times. The profits of bootlegging in Chicago proved to be prodigious, allowing an ample margin for the mollification of the forces of the law.

The competition proved to be exacting: every now and then Torrio would discover that his rivals had approached a speakeasy proprietor with the suggestion that he buy their beer instead of the Torrio-Capone brand, and on receipt of an unfavorable answer had beaten the proprietor senseless and smashed up his place of business.

But Al Capone had been an excellent choice as leader of the Torrio offensives; Capone was learning how to deal with such emergencies.

Within three years it was said that the boy from the Five Points had seven hundred men at his disposal, many of them adept in the use of the sawed-off shotgun and the Thompson sub-machine gun. As the profits from beer and “alky-cooking” (illicit distilling) rolled in, young Capone acquired more finesse—particularly finesse in the management of politics and politicians.

By the middle of the decade he had gained complete control of the suburb of Cicero, had installed his own mayor in office, had posted his agents in the wide-open gambling-resorts and in each of the 161 bars, and had established his personal headquarters in the Hawthorne Hotel. He was taking in millions now.


Torrio was fading into the background; Capone was becoming the Big Shot. But his conquest of power did not come without bloodshed. As the rival gangs—the O’Banions, the Gennas, the Aiellos—disputed his growing domination, Chicago was afflicted with such an epidemic of killings as no civilized modern city had ever before seen, and a new technic of wholesale murder was developed.

One of the standard methods of disposing of a rival in this warfare of the gangs was to pursue his car with a stolen automobile full of men armed with sawed-off shotguns and sub-machine guns; to draw up beside it, forcing it to the curb, open fire upon it—and then disappear into the traffic, later abandoning the stolen car at a safe distance.

Another favorite method was to take the victim “for a ride”: in other words, to lure him into a supposedly friendly car, shoot him at leisure, drive to some distant and deserted part of the city, and quietly throw his body overboard.

Still another was to lease an apartment or a room overlooking his front door, station a couple of hired assassins at the window, and as the victim emerged from the house some sunny afternoon, to spray him with a few dozen machine-gun bullets from behind drawn curtains.

But there were also more ingenious and refined methods of slaughter.

Take, for example, the killing of Dion O’Banion, leader of the gang which for a time most seriously menaced Capone’s reign in Chicago. The preparation of this particular murder was reminiscent of the kiss of Judas. O’Banion was a bootlegger and a gangster by night, but a florist by day: a strange and complex character, a connoisseur of orchids and of manslaughter.

One morning a sedan drew up outside his flower shop and three men got out, leaving the fourth at the wheel. The three men had apparently taken good care to win O’Banion’s trust, for although he always carried three guns, now for the moment he was off his guard as he advanced among the flowers to meet his visitors. The middle man of the three cordially shook hands with O’Banion— and then held on while his two companions put six bullets into the gangster-florist. The three conspirators walked out, climbed into the sedan, and departed.

They were never brought to justice, and it is not recorded that any of them hung themselves to trees in remorse. O’Banion had a first-class funeral, gangster style: a ten-thousand dollar casket, twenty-six truckloads of flowers, and among them a basket of flowers which bore the touching inscription, “From Al.”

Dion O’Banion, Capone’s major competition was eliminated.

In 1926 the O’Banions, still unrepentant despite the loss of their leader, introduced another novelty in gang warfare. In broad daylight, while the streets of Cicero were alive with traffic, they raked Al Capone’s headquarters with machine-gun fire from eight touring cars. The cars proceeded down the crowded street outside the Hawthorne Hotel in solemn line, the first one firing blank cartridges to disperse the innocent citizenry and to draw the Capone forces to the doors and windows, while from the succeeding cars, which followed a block behind, flowed a steady rattle of bullets, spraying the hotel and the adjoining buildings up and down.

One gunman even got out of his car, knelt carefully upon the sidewalk at the door of the Hawthorne, and played one hundred bullets into the lobby—back and forth, as one might play the hose upon one’s garden. The casualties were miraculously light, and Scarface Al himself remained in safety, flat on the floor of the Hotel Hawthorne restaurant; nevertheless, the bombardment quite naturally attracted public attention. Even in a day when bullion was transported in armored cars, the transformation of a suburban street into a shooting-gallery seemed a little unorthodox.

The war continued, one gangster after another crumpling under a rain of bullets; not until St. Valentine’s Day of 1929 did it reach its climax in a massacre which outdid all that had preceded it in ingenuity and brutality. At half-past ten on the morning of February 14, 1929, seven of the O’Banions were sitting in the garage which went by the name of the S. M. C. Cartage Company, on North Clark Street, waiting for a promised consignment of hijacked liquor.

A Cadillac touring-car slid to the curb, and three men dressed as policemen got out, followed by two others in civilian dress. The three supposed policemen entered the garage alone, disarmed the seven O’Banions, and told them to stand in a row against the wall. The victims readily submitted; they were used to police raids and thought nothing of them; they would get off easily enough, they expected.

But thereupon the two men in civilian clothes emerged from the corridor and calmly mowed all seven O’Banions with sub-machine gun fire as they stood with hands upraised against the wall. The little drama was completed when the three supposed policemen solemnly marched the two plainclothes killers across the sidewalk to the waiting car, and all five got in and drove off—having given to those in the wintry street a perfect tableau of an arrest satisfactorily made by the forces of the law!

Newspaper shot of the St. Valentine’s Massacre.

These killings—together with that of “Jake” Lingle, who led a double life as reporter for the Chicago Tribune and as associate of gangsters, and who was shot to death in a crowded subway leading to the Illinois Central suburban railway station in 1930—were perhaps the most spectacular of the decade in Chicago.

But there were over five hundred gang murders in all. Few of the murderers were apprehended; careful planning, money, influence, the intimidation of witnesses, and the refusal of any gangster to testify against any other, no matter how treacherous the murder, met that danger.

The city of Chicago was giving the whole country, and indeed the whole world, an astonishing object lesson in violent and unpunished crime. How and why could such a thing happen?

To say that prohibition—or, if you prefer, the refusal of the public to abide by prohibition—caused the rise of the gangs to lawless power would be altogether too easy an explanation. There were other causes: the automobile, which made escape easy, as the officers of robbed banks had discovered; the adaptation to peace-time use of a new arsenal of handy and deadly weapons; the murderous traditions of the Mafia, imported by Sicilian gangsters; the inclination of a wet community to wink at the by-products of a trade which provided them with beer and gin; the sheer size and unwieldiness of the modern metropolitan community, which prevented the focusing of public opinion upon any depredation which did not immediately concern the average individual citizen; and, of course, the easy-going political apathy of the times.

But the immediate occasion of the rise of gangs was undoubtedly prohibition—or, to be more precise, beer-running. (Beer rather than whisky on account of its bulk; to carry on a profitable trade in beer one must transport it in trucks, and trucks are so difficult to disguise that the traffic must be protected by bribery of the prohibition staff and the police and by gunfire against bandits.)

There was vast profit in the manufacture, transportation, and sale of beer. In 1927, according to Fred D. Pasley, Al Capone’s biographer, federal agents estimated that the Capone gang controlled the sources of a revenue from booze of something like sixty million dollars a year, and much of this—perhaps most of it—came from beer.

Fill a man’s pockets with money, give him a chance at a huge profit, put him into an illegal business and thus deny him recourse to the law if he is attacked, and you have made it easy for him to bribe and shoot.

There have always been gangs and gangsters in American life and doubtless always will be; there has always been corruption of city officials and doubtless always will be; yet it is ironically true, none the less, that the outburst of corruption and crime in Chicago in the nineteen-twenties was immediately occasioned by the attempt to banish the temptations of liquor from the American home.


The young thug from the Five Points, New York, had traveled fast and far since 1920. By the end of the decade he had become as widely renowned as Charles Evans Hughes or Gene Tunney. He had become an American portent. Not only did he largely control the sale of liquor to Chicago’s ten thousand speakeasies; he controlled the sources of supply, it was said, as far as Canada and the Florida coast.

He had amassed, and concealed, a fortune the extent of which nobody knew; it was said by federal agents to amount to twenty millions. He was arrested and imprisoned once in Philadelphia for carrying a gun, but otherwise he seemed above the law.

He rode about Chicago in an armored car, a traveling fortress, with another car to patrol the way ahead and a third car full of his armed henchmen following behind; he went to the theater attended by a body-guard of eighteen young men in dinner coats, with guns doubtless slung under their left armpits in approved gangster fashion.

When his sister was married, thousands milled about the church in the snow, and he presented the bride with a nine-foot wedding cake and a special honeymoon car; he had a fine estate at Miami where he sometimes entertained seventy-five guests at a time; and high politicians—and even, it has been said, judges—took orders from him over the telephone from his headquarters in a downtown Chicago hotel.

And still he was only thirty-two years old. What was Napoleon doing at thirty-two?

A successful Al Capone.

Meanwhile gang rule and gang violence were quickly penetrating other American cities. Toledo had felt them, and Detroit, and New York, and many another. Chicago was not alone. Chicago had merely led the way.

* * *

By the middle of the decade it was apparent that the gangs were expanding their enterprises. In Mr. Pasley’s analysis of the gross income of the Capone crew in 1927, as estimated by federal agents, the item of $60,000,000 from beer and liquor, including alky-cooking, and the items of $25,000,000 from gambling-establishments and dog-tracks, and of $10,000,000 from vice, dance-halls, roadhouses, and other resorts, were followed by this entry: Rackets, $10,000,000.

The bootlegging underworld was venturing into fresh fields and pastures new.

The word “racket,” in the general sense of an occupation which produces easy money, is of venerable age: it was employed over fifty years ago in Tammany circles in New York. But it was not widely used in its present meaning until the middle nineteen-twenties, and the derived term “racketeering” did not enter the American vocabulary until the year when Sacco and Vanzetti were executed and Lindbergh flew the Atlantic and Calvin Coolidge did not choose to run—the year 1927.

The name was a product of the Postwar Decade; and so was the activity to which it was attached.

Like the murderous activities of the bootlegging gangs, racketeering grew out of a complex of causes. One of these was violent labor unionism. Since the days of the Molly Maguires, organized labor had now and again fought for its rights with brass knuckles and bombs.

During the Big Red Scare, the labor unions had lost the backing of public opinion, and Coolidge Prosperity was making things still more difficult for them by persuading thousands of their members that a union card was not the only ticket to good fortune. More than one fighting labor leader thereupon turned once more to dynamite in the effort to maintain his job and his power.

Gone was the ardent radicalism of 1919, the hope of a new industrial order; the labor leader now found himself simply a man who hoped to get his when others were getting theirs, a man tempted to smash the scab’s face or to blow the roof off the anti-union factory to show that he meant business and could deliver the goods.


In many cases he turned for aid to the hired thug, the killer; he protected himself from the law by bribery or at least by political influence; he connived with business men who were ready to play his game for their own protection or for profit.

These unholy alliances were now the more easily achieved because the illicit liquor trade was making the underworld rich and confident and quick on the trigger and was accustoming many politicians and business men to large-scale graft and conspiracy.

Gangsters and other crafty fellows learned of the labor leader’s tricks and went out to organize rackets on their own account. Thus by 1927 the city which had nourished Al Capone was nourishing also a remarkable assortment of these curious enterprises.

Some of them were labor unions perverted to criminal ends; some were merely conspiracies for extortion masquerading as labor unions; others were conspiracies masquerading as trade associations, or were combinations of these different forms.

But the basic principle was fairly uniform: the racket was a scheme for collecting cash from business men to protect them from damage, and it prospered because the victim soon learned that if he did not pay, his shop would be bombed, or his trucks wrecked, or he himself might be shot in cold blood—and never a chance to appeal to the authorities for aid, because the authorities were frightened or fixed.

There was the cleaners’ and dyers’ racket, which collected heavy dues from the proprietors of retail cleaning shops and from master cleaners, and for a time, so completely controlled the industry in Chicago that it could raise the price which the ordinary citizen paid for having his suit cleaned from $1.25 to $1.75.

A cleaner and dyer who defied this racket might have his place of business bombed, or his delivery truck drenched with gasoline and set on fire, or he might be disciplined in a more devilish way: explosive chemicals might be sewn into the seams of trousers sent to him to be cleaned.


There was the garage racket, product of the master mind of David Ablin, alias “Cockeye” Mulligan: if a garage owner chose not to join in the Mid-West Garage Association, as this enterprise was formally entitled, his garage would be bombed, or his mechanics would be slugged, or thugs would enter at night and smash windshields or lay about among the sedans with sledge-hammers, or tires would be flattened by the expert use of an ice-pick.

There was the window-washing racket; when Max Wilner, who had been a window-washing contractor in Cleveland, moved to Chicago and tried to do business there, and was told that he could not unless he bought out some contractor already established, and refused to do so. He was not merely slugged or cajoled with explosives—he was shot dead.

The list of rackets and of crimes could be extended for pages; in 1929, according to the State Attorney’s office, there were ninety-one rackets in Chicago, seventy-five of them in active operation, and the Employers’ Association figured the total cost to the citizenry at $136,000,000 a year.

As the favorite weapon of the bootlegging gangster was the machine gun, so the favorite weapon of the racketeer was the bomb. He could hire a bomber to do an ordinary routine job with a black-powder bomb for $100, but a risky job with a dynamite bomb might cost him all of $1,000.

In the course of a little over fifteen months—from October 11, 1927, to January 15, 1929—no less than 157 bombs were set or exploded in the Chicago district, and according to Gordon L. Hostetter and Thomas Quinn Beesley, who made a careful compilation of these outrages in “It’s a Racket,” there was no evidence that the perpetrators of any of them were brought to book.

A merry industry, and reasonably safe, it seemed—for the racketeers. Indeed, before the end of the decade racketeering had made such strides in Chicago that business men were turning in desperation to Al Capone for protection; Capone’s henchmen were quietly attending union meetings to make sure that all proceeded according to the Big Shot’s desires, and it was said that there were few more powerful figures in the councils of organized labor than the lord of the bootleggers had come to be.


Racketeering, like gang warfare, had invaded other American cities, too. New York had laughed at Chicago’s lawlessness, had it? New York was acquiring a handsome crop of rackets of its own—a laundry racket, a slot-machine racket, a fish racket, a flour racket, an artichoke racket, and others too numerous to mention.

In every large urban community the racketeer was now at least a potential menace. In the course of a few short years he had become a national institution.

* * *

The prohibition problem, the gangster problem, the racket problem: as the Post-war Decade bowed itself out, all of them remained unsolved, to challenge the statesmanship of the nineteen-thirties.

Still the rum-running launch slipped across the river, the alky-cooker’s hidden apparatus poured forth alcohol, entrepreneurs of the contraband liquor industry put one another “on the spot,” “typewriters” rattled in the Chicago streets, automobiles laden with roses followed the gangster to his grave, professional sluggers swung on non-union workmen, bull-necked gentlemen with shifty eyes called on the tradesman to suggest that he do business with them or they could not be responsible for what might happen, bombs reduced little shops to splintered wreckage; and tabloid-readers, poring over the stories of gangster killings, found in them adventure and splendor and romance.

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