The Outfit Read online

  The Fly in the Ointment

  The suffocating restrictions of Volstead seemed all-inclusive, but they were not. Although selling booze was by and large illegal, drinking alcohol was just fine. Added to the fact that the Eighteenth Amendment had absolutely no effect on America’s unquenchable thirst, it was only a matter of time before the largest underground economy in history was launched. It was known as bootlegging.

  Since the earliest days of the New World’s western expansion, when cowboys had illegally smuggled alcohol in their knee-high boots to their Native American victims, “bootlegging” had been an integral part of the American fabric. With the advent of twentieth-century prohibition, the lure of the underground booze business became almost irresistible: astronomical profits combined with virtually no risk made a powerful fusion. It cost $5 to produce one barrel of beer that retailed for $55 minimum. The profit in hard liquor was higher still. George Remus, the powerful lawyer-turned-bootlegger from Ohio, earned $40 million in three years, a staggering amount for the time.

  Increasing the temptation to bootleg was that in 1923 the federal government employed merely fifteen hundred prohibition agents nationwide. Making matters worse, the agents were grossly underpaid (earning less than garbage collectors) and were thus easily corrupted by the big-spending bootleggers. In some instances the agents moonlighted as chauffeurs for their supposed targets. On the rare occasions when a “collar” was made, the feds imposed the relatively microscopic fine of $1,000.

  Underpaid prohibition agents and thirsty soldiers returning from World War I made certain that drinking would remain America’s favorite pastime. The federates had nowhere to turn for support, since corrupted officials were ensconced at every level of government, up to and including the White House. President Harding, rendered vulnerable as a result of an affair with a twenty-year-old who had given birth to his love child, was under the control of his pro-booze advisers. His attorney general, Harry Daugherty, was later found to have been on the payroll of one of the nation’s most powerful bootleggers, George Remus. Remus had been paying Daugherty the astronomical sum of $350,000 per year to allow the booze to flow.

  No locale was better positioned to take advantage of bootlegging’s riches than the city on Lake Michigan’s west bank. And nowhere was this obvious rags-to-riches path more adroitly perceived than in America’s “second city.” Named for the Ojibwa Indian word for the foul-smelling, river-clogging “wild onion” (checagou), it had already elevated political corruption to an art form. Chicago, the future home of The Outfit, embraced prohibition with open arms.

  “That Toddlin’ Town"

  Geography and geology play pivotal roles in the character of any city. Chicago’s placement on the map dictated that eastern urbanity come face-to- face with the take-the-law-into-your-own-hands mentality of the recently opened Wild West. After its incorporation in 1837, Chicago became the gateway to this new frontier and as such was guaranteed a steady stream of tourist business. Literally hundreds of wagons, overflowing with anxious homesteaders, transited Chicago every day.1

  Chicago soon amassed a glut of discretionary money, its coffers bulging with profits from manufacturing, commodities auctions, and huge stockyards that “rendered” seventeen million head of Western cattle a year. The party was on, and with the swiftness of a barroom pickpocket, Chicago became transformed into “That Toddlin’ Town.” Hotels and saloons were jammed with a mostly male clientele who had set out from the East in advance of the womenfolk. And these adventurers saw Chicago as their last chance for a little TLC before their trek into the harsh Western frontier. What transpired next was inevitable: Where there are unsupervised males there are saloons; where there are saloons, there are gambling and girls. The gamblers’ haunts acquired their own colorful nicknames, such as Hair-Trigger Block, Thieves Corner, and Gambler’s Row.

  Not far behind the saloon owners came the con men and swindlers. On some occasions, the con men were the saloon owners. One such character was Mickey Finn, who operated two establishments on Whiskey Row. Finn’s now infamous concoction, The Mickey Finn Special, was a drink tainted with a secret powder that rendered the drinker unconscious. While touring the twilight zone, the unfortunate reveler had his pockets emptied by the unscrupulous Finn. As they had throughout time, the criminal element found refuge in a district that seemed to be earmarked just for them. And it was one of the most bizarre vice districts imaginable.

  The Underworld

  If the good citizens of Chicago desired a law-abiding community in which to plant roots, geology conspired with geography to stack the cards in defiant opposition. For although Chicago seemed to be the right place to erect a city, nature had other ideas. The city, it turned out, was built on a smelly swamp/marsh, which was a sort of primordial soup for the gangster empires of the future. By the late 1850s, torrents of mud threatened to engulf the town, which had no paved streets. Cracks in the wooden slabs that functioned as thoroughfares oozed the muck around the wheels of carriages and the shins of well-dressed ladies. Mud Town and Slab Town were added to the list of unflattering nicknames for Chicago.

  The city fathers concocted an ingenious, if optimistic, solution to the muddy onslaught: jack up the entire city ten feet while fortifying the surface with stone. Given that the buildings themselves were constructed from relatively light wood, the idea was deemed feasible. Thus, for ten years Chicago existed on stilts, creating a cavernous “underworld,” as it came to be known. Soon, the underworld gave shelter to a repellent assemblage of humanity loosely commanded by Chicago’s first criminal-empire czar, Roger Plant.

  An immigrant boxer from England, Plant built a two-story paean to perversity called Under the Willows. The first floor consisted of round-the- clock boozing and gambling; the second tier was the domain of more than two hundred prostitutes, whose window shades were lettered on the outside with the slogan Why Not?

  As unsavory as the Willows was, it paled in comparison to the nether region for which it served as a main point of entry. For just below Plant’s “Barracks” was a labyrinthine maze of tunnels, rooms, and underground streets that drew, according to Jay Robert Nash, “hundreds of pickpockets, jackrollers, highwaymen, and killers for hire, the most fearsome collection of hoodlums anywhere in the U.S. at the time."

  But by far the most loathsome aspects of the underworld were its crimes against women. In this dungeonlike world, young girls were often forced into “the life,” otherwise known as prostitution. In standard operating procedure, “ropers” scoured the country for fourteen- and fifteen-year-old girls who could be lured to Chicago with promises of a big payday. Upon arrival, these girls were raped and otherwise terrorized into submission, kept pliant with opium, and assigned to whichever whorehouse bought them (for a couple hundred bucks plus a percentage of their earnings). For the next few years, while their youthfulness was still in demand, the girls paid their “owner” 60 to 90 percent of their ten-dollar trick fee. When their skin became ravaged by disease, they were tossed out on the streets only to succumb to drug overdoses. It was called white slavery, and it could be argued that it was every bit as brutal as the black variety.2

  The wanton criminality flourished in large part because Chicago maintained a police department in name only. In 1850, with an exploding population of eighty thousand, there existed only nine “city watch marshals” - as no police department had yet been established. Five years later - and too little too late - a minimalist Chicago Police Department was organized. In five more years, Chicago mayor Long John Wentworth actually decreased the force to a mere sixty cops.

  Word traveled fast throughout the nation’s criminal network. Soon Chicago sustained an influx of criminals from New Orleans, Mississippi, New York, and virtually every burg with a train depot or a healthy horse. At this turbulent juncture, the first true crime lord, Michael Cassius McDonald, appeared. A resident of “Hair-Trigger Block,” McDonald was a noted gambler, and among underworld successes the first to appreciate the importanc
e of the political fix. After coalescing the city’s riffraff into “McDonald’s Democrats,” he engineered the election of Mayor Carter Harrison in 1879. As his reward, McDonald gained the exclusive bookmaking franchise for all Chicago and Indiana. His gambling parlor, The Store, was known as the unofficial City Hall. McDonald, who was known to hate policemen, was once approached by two cops for a two-dollar donation. “We’re burying a policeman,” one of them said, to which Mike responded, “Here’s ten dollars. Bury five of them."

  McDonald’s organization coined the term syndicate to denote his crime consortium. The moniker would be appropriated much more infamously by a Chicago gang of the twentieth-century.

  In 1871 denizens of the underworld acquired still another source of revenue: looting. On the night of October 8, after a severe, record-shattering drought during which a scant one inch of rain fell in four months, a cow in the barn on Mrs. Catherine O’Leary’s Southwest Side farm knocked over a lantern. Fueled by ferocious gusts that have earned the city still another moniker, The Windy City, the barn fire escalated into the Great Chicago Fire. When it finally ended thirty-six brutal hours later, eighteen thousand mostly wooden buildings that had once concealed the underworld were incinerated. The city sustained more than five hundred deaths and was saddled with more than ninety-eight thousand newly homeless citizens. Fully half the city was consumed. Eyewitnesses described the horrific aftermath: like a pack of rats emerging from the underworld, the con men, scalawags, hoodlums, and whores descended on the ruins, looting anything that had not turned to cinders. Local clergy intoned that God’s wrath, not nature’s, was punishing this wicked metropolis. The Sodom and Gomorrah analogy was heard more than once in sanctimonious sermons. In time the local assessment became a national one.

  On the positive side, the fire afforded Chicago a unique opportunity to rebuild the entire city utilizing the most recent strides in engineering and design architecture. In a mere three years the city was transformed into a distinctly modern city and one of the most potent engines for commerce in the world. Soon many of the world’s first skyscrapers dominated the Windy City skyline.

  Again, word got out just how appealing the Second City had become. With immigration unchecked and unregulated, the population swelled to over two million by 1900. One half million Poles arrived along with more than one hundred thousand Italians, and still more Germans, Swedes, Jews, etc., all gravitating to their ethnic enclaves.

  Although the Chicago of the Gay Nineties achieved many noteworthy civic successes (especially its financial institutions, universities, and museums), it was also a nutrient-rich petri dish for the diseases of crime and corruption. The anemic police department numbered only eleven hundred (vs. a 2.1 million population). More than a dozen vice districts sprang up, with appropriate names such as The Black Hole, Bad Lands, Satan’s Mile, Dead Man’s Alley, and Hell’s Half Acre. Crime gangs flourished throughout the city. A 1927 study counted 1,313 gangs, which boasted over twenty-five thousand members.

  At the lowest street level, crime was often inseparable from the gambling element. Unlike other cities, Chicago was content to allow its illegal policy (numbers) rackets to be controlled by the blacks of the South Side. More than five hundred “policy stations,” run almost exclusively by brothers Edward and George Jones, thrived on the South Side alone.

  In the Italian enclaves, criminals embraced a different means to riches: gang terrorism. Given Italy’s turbulent history, it is small wonder many of its citizens distrust authority and seek riches and security in fiercely antiestablishment gangs. For much of the millennium Italy was overrun with foreign occupation. The list of oppressive foreign rulers is daunting: Spanish Bourbons, Greeks, Carthaginians, Arabs, Normans, and French, to name a few. When the invaders were finally cast out in the nineteenth century, the southern regions of Italy did not escape oppression - this time from the northern Romans and Neapolitans. This is to say nothing of Sicilians, who were held in disdain by all Italians and thus trusted no one. In sum, a certain type of crime - the sort that flouts authority - was widely considered an honorable way to get ahead.

  The Italian Immigrant Experience

  Upon arrival, the Italian-Sicilian masses were met with intolerable prejudice and discrimination, which only served to enforce their fears. Considered “less than white” by fairer-skinned northern Europeans, the Italian experience most closely resembled the racism experienced by African-Americans. The respected Washington Post newspaper was among those justifying the prejudice: “The Germans, the Irish, and others . . . migrate to this country, adopt its customs, acquire its language, master its institutions, and identify themselves with its destiny. The Italians never. They remain isolated from the rest of any community in which they happen to dwell. They seldom learn to speak our tongue, they have no respect for our laws or our form of government, they are always foreigners."

  From their arrival in the 1890s through at least 1915, Italians were regularly lynched in states from Florida to Colorado. Indeed, the worst mass lynching in U.S. history involved the brutal murders of eleven innocent Italian men in New Orleans on March 14,1891. In the hysteria that followed, one of the victims’ young sons was taken to safety by a Cajun woman, who fled with the boy up the river to Chicago. That boy, Joseph Bulger (Imburgio), went on to graduate law school at age twenty, then became one of the most influential behind-the-scenes legal advisers, or consigliere, for Chicago’s coming empire of crime.

  Persecution was the ugliest obstacle confronting the Italian immigrants, but not the only one. With an illiteracy rate (57.3 percent) that was nearly triple that of other new arrivals, Italian-Sicilian immigrants were forced to accept jobs no other immigrants wanted: ragpicker, chimney sweep, garbage salvager, ditchdigger - anything to get started. In the South, where recently freed slaves were less than enthusiastic about their tasks, Italians were thrilled to find any work. Richard Gambino wrote: “Italian labor seemed like a God-sent solution to replace both nigger and mule. The Sicilians worked for low wages and, in contrast to the blacks’ resentment, seemed overjoyed to be able to make the little money paid them.’

  Against the odds, the Italian immigrants succeeded in gaining a foothold in the New World. And despite the perception of a crime-prone Italian subculture, the facts reveal just the opposite. Consider the issue of prostitution. Whereas poor girls from most every race and nationality were represented in the nation’s bordellos, Italian girls were curiously immune to the temptation - their strong family ties made such a choice unthinkable. After the New Orleans lynchings, a follow-up investigation by the Wickersham Commission discovered that “Italians were charged with only four of the 543 homicides committed in New Orleans from 1925 to 1929.” The perception of “lawless” Italians, the study concluded, “seems hardly justifiable."

  There were, of course, Italian gangs - just as there were gangs of every ethnicity - and the Italian gangs arguably worked harder than their immigrant counterparts. Although they technically lived in America, the Italian gangs existed in a country of their own imaginations, filled with apprehension, fierce independence, and old-world mystique. Young Italian gang leaders were known to stare into mirrors in efforts to perfect “the look,” the menacing, unblinking stare that sent shivers through its unlucky recipient. In Chicago, in their Near West Side haunt called The Patch, Italian gangs utilized a terror method that had flourished for centuries in the Old Country. La Mano Nera, or The Black Hand, was undoubtedly the quickest, most direct method for a tough punk to make a buck. Although commonly believed to be a crime society, the Black Hand was actually just a method of criminality. It involved nothing more sophisticated than the delivery of a death threat, or Black Hand note, to a prospering Italian immigrant. The note was often inscribed on paper that also bore the imprint of a hand in black ink. The threat would be rescinded in exchange for a payoff. Simple extortion.

  The Black Handers made their real mark on history by introducing the bomb as a terrorist weapon. More than three hundred Bla
ck Hand bombings and four hundred Black Hand murders went down between 1890 and 1920. When prohibition was enacted, the Black Handers, who by now numbered more than sixty gangs and even more individuals, were given a much more acceptable path out of their barrios and eventually into the lives of all American citizens - whether they knew it or not.

  Not-So-Strange Bedfellows

  Predictably, the denizens of this shadow economy required shielding from officials charged with enforcing the criminal code. For widescale criminal endeavors to succeed, the tacit approval of City Hall is a prerequisite. And Chicago’s unique charter made it the ideal arena in which lawbreakers could flourish.

  As if more fuel were needed to inflame Chicago’s lawless character, its peculiar system of government known as the ward system played a major role in making it a fertile crescent for corruption. Chicago is divided into fifty wards and three thousand voting precincts, the most coveted being the rich downtown First Ward. The essential features of the ward are the posts of elected alderman and appointed committeeman. The alderman serves the traditional role of legislator, voting on ordinances, budgets, etc. The position of committeeman, however, presents a powerfully seductive invitation to corruption.

  In the ward, the real power rested with the committeeman. “The reason was patronage,” wrote David Fremon. It was an elegantly simple design: the committeemen were granted by law the power to dispense jobs in return for political support. Most important, these appointments included judges and sheriffs. Kickbacks and favors lavished on the committeemen made the nonsalaried position a plum post for unethical pols. Once elected, the momentum of the incumbent, to say nothing of the gangsters’, increased exponentially. Subsequent reelections were pro forma in this perpetual-motion corruption machine. Fremon pointed out that the parties relied on “an army of precinct workers whose civil service - exempt jobs depended on how well they performed on election day.” Michael Killian described how the Democratic machine, installed after World War II, operated: “[The Democrats] put together a perpetual motion machine in Chicago that dispensed favors in return for votes, and so long as the voters knew where the favors were coming from, nothing changed . . . The Democratic Party in Chicago is simply a means for earning a living."