The Rise of American Gangsters

Chapter Opening

On a warm summer evening in 1890, a visitor strolling through the Bowery district of lower Manhattan would have encountered a world of dense, competing energies. Pushcart vendors crowded the sidewalks. Saloons spilled noise and light into the street. Tenement buildings rose six and seven stories, their windows dark with soot, their fire escapes draped with laundry. Children played in alleys while adults haggled at stalls selling secondhand clothes, cheap food, and goods of uncertain origin. And threading through it all, invisible to the casual eye but structurally present, was a network of criminal organizations that had grown alongside the city itself: street gangs that controlled blocks and corners, gambling operators who ran games from back rooms of saloons and barbershops, vice entrepreneurs who managed prostitution networks extending from seedy lodging houses to more elaborate establishments, and ward bosses who translated criminal connections into political power and political power back into criminal protection. The American gangster was not born in the 1920s. He, and occasionally she, had been building the foundations of organized criminal enterprise in American cities for decades before Prohibition made the phenomenon impossible to ignore.

This chapter examines the formative era of American organized crime, the decades between roughly 1860 and 1920, when street gangs evolved from crude neighborhood protection rackets into complex enterprises with political connections, territorial claims, diversified criminal revenues, and management structures capable of surviving the death or arrest of individual leaders. It is a story inseparable from the larger history of American urbanization, immigration, economic inequality, and political corruption. Understanding why organized crime flourished in the American city during this period requires understanding the city itself: its extraordinary growth, its social stratification, the weakness of its formal institutions, the power of informal ones, and the ways in which the line between legitimate and illegitimate enterprise was constantly negotiated, blurred, and crossed.

The rise of the American gangster was not simply a story of individual moral failure or immigrant pathology, as many observers of the era claimed. It was a structural story, rooted in specific economic and political conditions that made criminal organization not only possible but, for many participants, rational. In neighborhoods where legitimate economic opportunity was sharply constrained by poverty, discrimination, and the brutal rhythms of industrial labor, criminal enterprise offered something that factory work did not: autonomy, income, and a species of social status. In a political system riddled with corruption, criminal organizations offered votes, muscle, and money in exchange for protection from law enforcement. In a society that simultaneously prohibited many forms of pleasure and desired them intensely, criminal entrepreneurs built markets that the respectable economy refused to supply.

The geography of this story was concentrated but not confined. New York City was the largest stage, with its Five Points district, its Bowery gangs, its Hell's Kitchen Irish crews, and its later Italian and Jewish criminal networks. Chicago was a close rival, with its South Side gambling houses, its first-ward saloon politics, and the notorious Levee vice district that operated under explicit political protection for years. New Orleans had its own criminal traditions shaped by its distinctive history as a French and Spanish colonial city, a major port, and a place where racial categories were more complex and more permeable than in most American cities. San Francisco, Boston, Philadelphia, St. Louis, and a dozen other industrial cities all had their own versions of this story, shaped by local ethnic compositions, political cultures, and economic conditions.

What united these different urban criminal worlds was a set of common structural features. Criminal organizations nested within larger social and ethnic communities, drawing on networks of trust, loyalty, and shared identity that formal institutions could not easily penetrate. They provided services, including gambling, alcohol, prostitution, and money-lending, that large segments of the urban population wanted and that law and morality had placed beyond the reach of legitimate commerce. They built relationships with political machines that converted criminal resources into political protection and political protection into criminal profits. And they managed their internal affairs through a combination of hierarchy, personal loyalty, and strategic violence that anticipated the more elaborate organizational structures that would emerge in the Prohibition era.

This chapter also insists on complexity in understanding who the gangsters were and how different groups experienced the criminal underworld. For some young men from immigrant families, gang membership was a transitional phase, a way of establishing status in a neighborhood before moving into legitimate work. For others, it was a career that lasted decades and produced real wealth, however precarious. For the communities in which gangs operated, the relationship was deeply ambivalent: gangs provided certain protections and social services while also extracting tribute, generating violence, and corrupting the political institutions that neighborhoods needed to function. For reformers, the existence of organized crime in American cities was evidence of a political and moral crisis that demanded immediate attention. And for the political machines that depended on criminal relationships to sustain their power, the underworld was simply part of the ecology of urban governance, neither celebrated nor eliminated but managed.

By the time the United States entered the Prohibition era in 1920, the foundations of American organized crime had been laid over more than half a century of urban growth, political corruption, and criminal entrepreneurship. Understanding those foundations is essential to understanding what Prohibition produced and why it produced it so quickly and so dramatically. The gangsters of the 1920s did not appear from nowhere. They were the inheritors and refiners of a tradition of criminal organization that had been developing in American cities since the middle of the nineteenth century. Chapter 10 tells the story of how that tradition was built.

Learning Objectives

Guiding Historical Questions

Historical Context

The rise of organized crime in American cities cannot be understood apart from the extraordinary transformation that American society underwent in the decades following the Civil War. Between 1860 and 1920, the United States completed one of the most rapid industrializations in world history. The population of the country grew from roughly 31 million to more than 106 million. The urban population, meaning people living in cities and towns of more than 2,500 residents, increased from roughly 20 percent of the total to nearly 52 percent. Cities that had been modest commercial centers in 1860 became giant industrial metropolises by 1920. New York City's population grew from about 1.2 million in 1880 to nearly 5.6 million by 1920. Chicago, which barely existed as a city in 1840, had a population of 2.7 million by 1920. These cities grew not only in population but in physical extent, economic complexity, and social diversity, and the institutions of governance, law enforcement, and social order struggled, often unsuccessfully, to keep pace with the pace of change.

The engine of urban growth was immigration. Between 1880 and 1920, more than twenty million immigrants arrived in the United States, the vast majority from Southern and Eastern Europe. Italians, Jews from Russia and the Austro-Hungarian Empire, Poles, Czechs, Hungarians, Slovaks, Greeks, and many others poured into American cities in numbers that fundamentally reshaped the social geography of urban America. These immigrants settled overwhelmingly in specific neighborhoods, often organized along ethnic lines: the Lower East Side of Manhattan was heavily Jewish, certain sections of Brooklyn and the South Side of Chicago were Italian, particular neighborhoods in Boston were Irish, and so on. These ethnic enclaves provided crucial social support networks for newly arrived immigrants, but they also created conditions, including linguistic isolation, economic marginality, and distance from the formal institutions of American civic life, that criminal organizations could exploit and inhabit.

The economies of these neighborhoods were constrained and pressured in ways that formal economic statistics rarely captured. Immigrant workers were concentrated in the most dangerous, least well-paid, and least stable sectors of the industrial economy: garment factories, meatpacking plants, construction gangs, mining operations, and the casual labor markets of ports and railroad yards. Wages were low, hours were long, and employment was irregular. The industrial economy of this era offered most immigrant workers not a path to prosperity but a grinding struggle for survival. In such an environment, the appeal of criminal enterprise as an alternative route to income and status was real and rational, even if it was also dangerous and morally complex.

The political environment of American cities in this era was dominated by political machines: organizations built around ward-level patronage networks, ethnic loyalties, and the systematic exchange of votes for services. In New York, Tammany Hall had controlled Democratic Party politics for decades. In Chicago, similar organizations dominated local government. In Boston, Kansas City, Memphis, and elsewhere, machine politics shaped who got city contracts, who got jobs in city government, and who faced enforcement of the law and who did not. Political machines were not simply corrupt in the narrow sense. They served real functions in an era when formal social welfare institutions barely existed, providing coal in winter, food in emergencies, bail money when someone was arrested, and jobs in city government in exchange for votes and loyalty. But they also systematically tolerated vice and criminal enterprise in exchange for money and political support, creating the protective umbrella under which organized crime operated.

Law enforcement in this period was deeply inadequate to the challenge of controlling organized crime, partly because of institutional weakness and partly because of deliberate corruption. Urban police forces in the late nineteenth century were poorly trained, inadequately paid, politically appointed, and deeply embedded in the patronage systems of the machines they nominally served. Police officers expected to receive payments from gambling houses, saloons, and prostitution establishments in exchange for non-enforcement of the laws against these activities. Promotions within police departments were often purchased rather than earned. And the top leadership of urban police departments was frequently aligned with the political machines that tolerated or actively profited from the criminal enterprises the police were theoretically responsible for suppressing. In this environment, law enforcement against organized crime was not a realistic policy goal but a performance of civic virtue occasionally staged when public pressure demanded visible action.

All of these factors, the explosive growth of cities, the arrival of millions of immigrants with limited economic options, the dominance of machine politics, and the corruption of law enforcement, combined to create the specific historical conditions in which the American gangster emerged. This chapter examines how those conditions translated into the specific criminal organizations, enterprises, and relationships that shaped American urban life from the Civil War through the eve of Prohibition.

Chronology Preview

Major People, Groups, and Places

Core Vocabulary Preview

The following key terms appear throughout this chapter. Students should understand each term before proceeding to the main sections.

Street Gangs and Urban Crime

The street gang is among the oldest and most persistent forms of collective criminal behavior in American urban history. Long before the term "organized crime" entered common usage, cities like New York, Chicago, and New Orleans harbored networks of young men organized around neighborhood territory, ethnic identity, and mutual protection, and willing to use violence to defend their interests and enforce their claims. Understanding the street gang as a historical institution, rather than simply as a social problem or a symptom of individual pathology, requires examining the specific social, economic, and spatial conditions that produced it.

The earliest major American street gangs emerged in the slum neighborhoods of New York City during the 1820s and 1830s. The Five Points district of lower Manhattan, named for the intersection of five streets near what is now Foley Square, was among the most densely populated and desperately poor urban spaces in the Western world during this period. Former swampland that had been filled and developed cheaply, Five Points flooded frequently, bred disease, and attracted the most marginal populations of the city: free Black New Yorkers, Irish immigrants fleeing famine and poverty, and the urban poor of every origin who could afford nothing better. In this environment, gangs emerged as instruments of neighborhood protection, economic exploitation, and collective identity. The Plug Uglies, the Dead Rabbits, the Roach Guards, and the Shirt Tails were among the most notorious of the antebellum Five Points gangs, and their conflicts drew the attention of newspaper reporters and social reformers who described them in terms mixing genuine horror with sensationalism.

These early gangs were relatively simple in their organization. Leadership was typically informal and contested, based on physical dominance and charisma rather than formal hierarchy. Revenue came from petty theft, pickpocketing, the robbery of individuals who could be isolated from protection, and from whatever tribute the gang could extract from local businesses. Political connections, though nascent, were already present: gang members provided the muscle for ward politics, turning out votes on election day and intimidating opposition voters, in exchange for protection from arrest and occasional cash payments from machine politicians who found them useful.

The evolution from these relatively crude early formations toward more sophisticated criminal organizations accelerated after the Civil War, driven by several interconnected forces. The extraordinary growth of cities created larger and more complex criminal markets. The arrival of millions of new immigrants created new pools of potential recruits and new ethnic networks that criminal organizations could inhabit. The maturation of political machines created more stable and more profitable relationships between criminal enterprise and political power. And the accumulation of experience, as successful criminal operators learned from observation what worked and what did not, gradually produced more sophisticated organizational forms.

The Eastman Gang and the Five Points Gang

By the early twentieth century, New York's criminal landscape was dominated by two major gang organizations whose histories illustrate both the persistence and the evolution of American street gangs. The Eastman Gang, led by Monk Eastman, and the Five Points Gang, led by Paul Kelly, were rivals who between them controlled much of the criminal territory of lower Manhattan for nearly a decade.

Monk Eastman, born Edward Osterman in Brooklyn around 1873, was a physically imposing figure, reportedly standing nearly six feet tall and weighing over two hundred pounds, who built his gang from the street level up through a combination of personal violence and organizational talent. The Eastman Gang at its peak numbered perhaps a thousand members, organized into a loose hierarchy with Eastman at the top, a tier of trusted lieutenants below him, and a large base of young men who could be called upon for specific tasks, from pickpocketing and robbery to providing muscle in labor disputes or election-day violence. The gang's primary territory was the Lower East Side, and Eastman maintained his position there partly through violence and partly through an arrangement with Tammany Hall whereby the gang provided votes and muscle in exchange for protection from serious law enforcement.

Paul Kelly, born Paolo Vaccarelli, represented a somewhat different model of criminal leadership. Italian-born and more cosmopolitan in his self-presentation than Eastman, Kelly cultivated a persona of respectability, operating through the New Paul Kelly Association, a social club that served as a front for the Five Points Gang's criminal activities. Kelly's gang controlled territory on the Lower East Side south of Houston Street and engaged in similar activities to Eastman's organization, but Kelly was more attentive to building stable political relationships and diversifying his organization's revenue streams beyond simple street violence. His Five Points Gang became a training ground for a generation of future criminal leaders: Johnny Torrio and the young Al Capone both moved through its orbit in the early years of the twentieth century.

The rivalry between the Eastman Gang and the Five Points Gang produced periodic violence that alarmed even the Tammany Hall politicians who depended on both organizations. In 1903, a major battle between the two gangs on Rivington Street resulted in multiple casualties and attracted enough public attention that Tammany felt compelled to arrange a summit between Eastman and Kelly, settling the territorial dispute and reducing the visibility of gang violence. This episode was instructive: it demonstrated both the extent to which political machines exercised a moderating influence over gang conflict, and the extent to which that influence was motivated by self-interest rather than any concern for public safety.

Hell's Kitchen and the Irish Gangs

While lower Manhattan's gangs drew the most attention from newspapers and reformers, other neighborhoods produced their own criminal organizations with distinct characters shaped by their specific demographics and circumstances. Hell's Kitchen, the working-class neighborhood on Manhattan's West Side between roughly Thirty-Fourth and Fifty-Ninth Streets and between Eighth Avenue and the Hudson River, was dominated by Irish gangs whose organization reflected the specific social position of the Irish in American urban life.

Irish immigrants had arrived in America in enormous numbers during the famine years of the 1840s and 1850s, and while many had moved into more stable working-class and lower-middle-class positions by the late nineteenth century, those in Hell's Kitchen were concentrated in the most precarious sectors of the economy: dock labor, cartage, construction work on the expanding transit system, and the casual labor market of the waterfront. Gang membership in this context was deeply intertwined with work: the same networks of loyalty and mutual aid that organized gang activity also organized access to employment, particularly on the docks, where gang leaders often functioned as labor contractors, distributing work to their followers and extracting tribute from employers in exchange.

The Hudson Dusters and the Gophers were among the most notable Hell's Kitchen gangs of the early twentieth century. The Gophers at their peak may have numbered over five hundred members and engaged in a wide range of criminal activities from waterfront theft and burglary to protection rackets targeting local businesses. Their relationship with politics was mediated through the Democratic Party's West Side clubs, which depended on gang members to deliver votes and manage elections in exchange for protection. The Hell's Kitchen gangs never achieved the same degree of political prominence as the Tammany Hall operations downtown, partly because the West Side's denser network of legitimate working-class organization, including labor unions and fraternal societies, provided some counterweight to gang influence.

Chicago's Gang Landscape

Chicago's street gang history followed a somewhat different trajectory than New York's, shaped by the city's distinctive geography, its more recent founding, and the particular ethnic compositions of its neighborhoods. Chicago had no equivalent to New York's Five Points, partly because it had been settled later and its slum conditions, while severe, had not had as long to develop. Instead, Chicago's most significant criminal organizations in the pre-Prohibition era were organized less around territorial street gangs and more around specific economic activities, particularly gambling and vice, in particular neighborhoods and under particular political patronage arrangements.

This does not mean that Chicago lacked street violence. The city's ethnic neighborhoods, which included large Irish, Italian, Polish, Jewish, and African American communities, each with their own internal hierarchies and external tensions, generated substantial gang activity. But in Chicago, the pathway from street-level gang activity to more sophisticated criminal organization was mediated more directly through specific political figures and specific vice enterprises than in New York, where the sheer scale and density of the criminal environment produced more autonomous gang structures.

Gambling Operations

Of all the illegal enterprises that sustained American organized crime in the pre-Prohibition era, gambling was the most important, the most pervasive, and the most revealing about the nature of the relationship between criminal enterprise, political power, and public demand. Gambling was everywhere in late nineteenth-century American cities: in saloons and poolrooms, in barbershops and cigar stores, in elaborate private clubs accessible only to men of means, and in the street-level number games that gave the urban poor a daily encounter with the hope of sudden improvement in their circumstances. The diversity of gambling operations reflected the stratification of American urban society, with different games serving different classes and operating under different levels of criminal organization and political protection.

The simplest and most widespread form of urban gambling in this period was the policy game, also known as the numbers game or the lottery. Policy was a form of lottery in which players selected numbers from a large range, typically one to seventy-eight, and wagered small amounts, often just pennies, on their selections. Winning numbers were drawn daily, sometimes multiple times daily, and winners received payouts at odds that were substantially less than the true mathematical odds, providing the policy operators with a reliable profit margin. The game was accessible to everyone, regardless of how little money they had, and it attracted enormous participation in working-class and immigrant neighborhoods.

The policy game required organizational infrastructure to operate effectively. Policy wheels, the mechanisms by which numbers were drawn, needed to be operated and overseen. Collections of bets, typically gathered by "runners" who circulated through neighborhoods collecting slips and money, needed to be organized and the revenue accounted for. Payouts to winners needed to be made promptly enough to maintain player confidence. And the entire operation needed protection from police interference, which required the payment of regular bribes to precinct officers, district police captains, and in some cities to central police authorities or their political supervisors.

In New York, the policy game by the late nineteenth century had developed into a substantial industry, with multiple competing policy banks operating in different neighborhoods and under different political protection arrangements. John "Bet-a-Million" Gates and other prominent gambling figures of the era operated policy operations as explicit businesses, with hired employees, regular accounting, and systematic protection arrangements. The revenue from policy in major American cities was substantial: estimates of the total take from New York's policy operations in the 1890s ran to millions of dollars annually, with a significant portion flowing upward to political figures and law enforcement as protection payments.

The Gambling House

At the upper end of the gambling spectrum sat the gambling house, an establishment offering a variety of games, including faro, roulette, poker, and dice games, typically in more elaborate surroundings designed to attract middle-class and upper-class clientele. The great gambling houses of this era were significant establishments, some of them occupying elegant townhouses in respectable neighborhoods, employing dozens of workers, offering food, drink, and sometimes entertainment alongside their gaming operations, and attracting men of wealth and social position who desired the combination of excitement, exclusivity, and illegality that the gambling house provided.

The most celebrated gambling entrepreneur of the mid-nineteenth century was John Morrissey, whose career traced an arc from gang fighter to professional gambler to legitimate politician that illustrated the permeability of the boundary between criminal enterprise and respectable society in this era. Morrissey had been a prize fighter and a member of the Dead Rabbits gang in his youth, but he used the proceeds of his gambling operations to establish a racing track at Saratoga Springs, New York, that became the center of fashionable American horse racing. He was subsequently elected to Congress from New York and served two terms as a congressman before his death in 1878. His career was extreme in its particular combination of achievements, but its basic shape, criminally derived wealth converted into legitimate social status through strategic investment and political participation, anticipated a pattern that would become common in American organized crime.

Chicago's gambling industry in the late nineteenth and early twentieth centuries was organized around a small number of powerful figures who operated under explicit political protection from the machine politicians who controlled the relevant wards and precincts. Mont Tennes was the most powerful of these figures in the first two decades of the twentieth century. Tennes built a near-monopoly on poolroom betting on horse racing in Chicago through a combination of organizational skill and political connection, controlling the wire service that transmitted race results to poolrooms and using that control to extract tribute from gambling operations throughout the city. His organization anticipated the syndicate structures of the Prohibition era in its geographic reach, its vertical integration of different parts of the gambling business, and its systematic use of political protection as a business resource rather than as an occasional necessity.

Gambling and Social Life

Understanding gambling as a historical phenomenon in this period requires moving beyond the perspective of law enforcement and reformers, who saw it primarily as a source of social harm, to consider why gambling was so enormously popular in working-class and immigrant communities. For workers whose wages provided a meager and uncertain existence, the policy game offered the daily experience of hope: for a few cents, a worker could purchase a ticket on the possibility of a sudden windfall that might solve, however temporarily, the grinding problem of poverty. The irrationality of the gamble from an expected-value perspective is obvious, but expected-value calculations do not capture the psychological and social reality of what the policy game provided to its participants. It was a community activity as much as a financial one, a shared ritual of aspiration played out daily in neighborhood stores and on street corners that knit together the social fabric of communities in ways that observers focused on its economic exploitation often missed.

Gambling also intersected with the social institutions of immigrant and working-class neighborhoods in ways that made its elimination difficult even when reform movements succeeded in disrupting specific operations. Saloons, which were among the most important social institutions in working-class neighborhoods, typically hosted gambling of various kinds as part of their normal operation. The poolroom, ostensibly a venue for the game of billiards, was in practice often primarily a venue for off-track betting on horse races. These establishments were not marginal to community social life; they were central to it, serving functions of male socialization, political organizing, labor recruiting, and credit extension that had no ready legitimate substitutes. Reform campaigns that attacked gambling without attending to the social functions it served often found that communities resisted their efforts, not because communities approved of exploitation, but because the organizations being targeted provided real services alongside the extraction.

Vice Districts

The vice district, a geographically defined area of a city within which the sale of sex, alcohol, and gambling was tolerated or explicitly permitted by local political authorities, was one of the most distinctive institutional forms of American urban criminal enterprise in the late nineteenth and early twentieth centuries. Vice districts existed in virtually every major American city during this period, under different names and with different formal statuses, but sharing a common functional logic: the concentration of socially disapproved activities in specific spaces, under the supervision of political and criminal authority, in ways that generated reliable revenue for those authorities while making the activities invisible to the middle-class neighborhoods that would otherwise find them offensive.

The logic of the vice district from the perspective of its political managers was straightforward. Vice was not going to disappear simply because it was illegal. The demand for the services provided in vice districts, alcohol consumption, commercial sex, and gambling, was too widespread, too deep, and too connected to fundamental aspects of male working-class and upper-class social life to be eliminated by prohibition. If vice could not be eliminated, it could be managed: concentrated in specific areas, controlled by specific operators who paid regular tribute to political and law enforcement authorities, and kept sufficiently out of sight that respectable citizens could maintain their own self-image of living in a moral community. The vice district was thus a political compromise between the reality of urban demand for prohibited activities and the formal moral commitments of American public life.

The Levee District, Chicago

Chicago's Levee district, located in the First Ward near the downtown business district, was the most extensively documented vice district in American history, partly because of the extraordinary detail in which muckraking journalists and reform investigators described it, and partly because the political figures who protected it were so brazen in their public celebration of the arrangement. The two First Ward aldermen who presided over the Levee for nearly two decades, John "Bathhouse John" Coughlin and Michael "Hinky Dink" Kenna, were genuinely colorful political figures who made no particular effort to conceal the nature of their arrangements with the vice operators they protected.

Coughlin, a former bathhouse attendant of limited intellectual attainment but considerable political instinct, and Kenna, a diminutive and shrewd saloonkeeper, had built their political power on the First Ward's distinctive social geography. The ward included not only the most concentrated vice operations in the city but also a large population of transient workers, seasonal laborers, and the urban poor who inhabited the cheap lodging houses, saloons, and mission dormitories of the area. Coughlin and Kenna controlled this population through a combination of services, including meals, lodging vouchers, and bail money in emergencies, and organization, including the notorious First Ward Ball, an annual fundraising event whose guest list mixed Chicago's political elite with its most prominent vice operators. The Ball was simultaneously a political fundraiser, a demonstration of machine power, and a celebration of the arrangement between politics and crime that made the Levee possible.

The Levee at its height contained several hundred establishments ranging from cheap dives to the elaborate Everleigh Club, a brothel of such elegance and reputation that it attracted visitors from across the country and became something of a perverse tourist attraction. Operated by sisters Ada and Minna Everleigh from 1900 to 1911, the Everleigh Club charged prices far above those of ordinary establishments, employed musicians and maintained a wine cellar, and attracted a wealthy clientele whose patronage gave the club a certain degree of protection from the police harassment that lower establishments experienced. The Everleighs paid regular tribute to the political and law enforcement authorities who permitted their operation, making their club one of the most profitable enterprises in the criminal economy of early-twentieth-century Chicago.

The Levee finally came to an end under pressure from the reform administration of Mayor Carter Harrison Jr., who ordered the closure of the district's brothels in 1912. The closure of the Levee was genuinely significant: it ended the era of openly operated, politically protected vice districts in Chicago. But it did not end the vice industries themselves. Prostitution, gambling, and illegal alcohol sales continued in Chicago after 1912, but they did so in more dispersed, more covert, and more organizationally sophisticated forms. The destruction of the Levee accelerated the professionalization of criminal enterprise in Chicago, forcing vice operators to develop more elaborate protection arrangements, more sophisticated organizational structures, and more geographically dispersed operations. In this sense, the reform movement's success in closing the Levee paradoxically contributed to the more dangerous organized crime that would emerge in the Prohibition era.

Storyville, New Orleans

New Orleans offered a distinctive model of vice district management in its Storyville district, established by a city ordinance in 1897 and named after Alderman Sidney Story, who had introduced the legislation. Unlike Chicago's Levee, which operated through informal political protection of technically illegal activities, Storyville was created by explicit legislation that delimited a specific geographic area within which prostitution would be tolerated, regulated, and taxed. The ordinance did not legalize prostitution outright but rather specified that the city would not enforce existing laws against it within the designated boundaries.

Storyville operated for twenty years, becoming internationally famous as a center of jazz music as well as commercial sex. The district's establishments ranged from ornate parlor houses catering to wealthy clients to cheap "cribs," small rooms in which individual women received clients for minimal amounts. The racial composition of Storyville was complex, reflecting New Orleans's distinctive history as a French and Spanish colonial city with a significant Creole population that occupied an ambiguous position in the city's racial hierarchy. Black and white women worked in Storyville, sometimes in the same establishments, in an arrangement that would have been impossible in most other American cities of the era. The district was also a significant venue for African American musicians, and several of the most important figures in early jazz history, including Jelly Roll Morton, performed in Storyville's establishments during the district's operation.

Storyville was closed in 1917 by order of the United States Secretary of the Navy, who had authority to prohibit prostitution near military installations, on the grounds that the nearby naval station at Algiers made the district a threat to military health and discipline. The closure of Storyville, like the closure of Chicago's Levee, dispersed vice activities rather than eliminating them, and it contributed to the migration of jazz musicians from New Orleans to Chicago and New York, where their music found new audiences and began its transformation into the central American art form it would become.

Political Machines and Criminal Enterprise

The relationship between political machines and criminal organizations was not a corruption of American democracy but a structural feature of American urban governance in the late nineteenth and early twentieth centuries, built into the institutional fabric of city politics in ways that made it remarkably durable and resistant to reform. Understanding this relationship requires moving beyond the language of individual moral failure, which dominated reformers' accounts of machine corruption, to examine the structural logic that made the machine-crime symbiosis rational and functional for all parties involved.

Political machines needed three things to maintain their power: votes, money, and organizational capacity. Votes came primarily from working-class and immigrant communities whose members depended on machine services and whose loyalty the machine cultivated through systematic patronage. Money came from a variety of sources, including city contracts awarded to machine-connected firms, assessments on the salaries of city employees who owed their jobs to machine patronage, and the protection payments extracted from gambling houses, saloons, and brothels. Organizational capacity came from the ward and precinct structure through which the machine maintained contact with its constituents, delivering services, gathering information, and mobilizing voters.

Criminal organizations needed political machines primarily for protection: protection from law enforcement, protection from prosecution, and protection from the reform movements that periodically threatened to close their operations. A gambling house that paid regular tribute to the relevant precinct captain, district attorney's office, and political boss could operate with minimal interference. One that did not make these payments faced the constant threat of arrest, prosecution, and business disruption. The protection that political machines provided was thus not a luxury but a fundamental cost of doing business in the illegal economy.

Tammany Hall and New York's Criminal Ecology

No institution more fully embodied the machine-crime relationship than Tammany Hall, the Democratic Party organization that controlled New York City politics for much of the nineteenth and early twentieth centuries. Under a succession of leaders, including William Marcy Tweed, John Kelly, Richard Croker, and Charles Murphy, Tammany developed what amounted to a franchise system for urban vice, in which political protection was available to gambling operators, saloon keepers, and brothel managers who paid the appropriate tribute and maintained the appropriate political loyalties.

The mechanics of Tammany's relationship with criminal enterprise were extensively documented by the Lexow Committee, which conducted hearings in 1894 and took testimony from police officers, gambling operators, and political figures about the specific arrangements through which protection was provided and payment collected. The testimony revealed a system of extraordinary organizational sophistication. Police captains paid substantial sums for their appointments and expected to recoup these investments through tribute collected from vice operators in their precincts. The amounts were not arbitrary but followed a systematic schedule: gambling houses paid one amount, saloons another, brothels another. The collected tribute moved upward through the police hierarchy, with portions retained at each level and the balance forwarded to the political figures to whom the police owed their appointments.

Richard Croker, who led Tammany from 1886 to 1902, was the most powerful figure in New York City politics during this period and one of the most brazen in his enrichment from political power. Croker entered Tammany as a young Irishman of modest means and retired to Ireland as a multimillionaire, his fortune accumulated through political protection arrangements, city contracts, and investments in real estate and business facilitated by his political connections. His career demonstrated that the machine-crime relationship was not simply about tolerating criminal enterprise at a distance but about the direct personal enrichment of political figures through the systematic taxation of vice.

The Tammany system was also a system of ethnic politics, and the ethnic dimension of machine power had direct consequences for the organization of criminal enterprise. As the composition of immigrant populations shifted from predominantly Irish to increasingly Italian and Jewish by the early twentieth century, Tammany adapted, incorporating new ethnic constituencies into its structure and creating new protection arrangements with the emerging Italian and Jewish criminal entrepreneurs who were building organizations in the city's immigrant neighborhoods. This ethnic flexibility was one of Tammany's sources of organizational resilience: it could accommodate new groups by extending the same protection arrangements to them that it had previously reserved for the Irish.

Chicago's First Ward

The political management of vice in Chicago differed from New York's primarily in being more territorially concentrated and more openly celebrated by its principal managers. The First Ward aldermen Coughlin and Kenna operated what amounted to a franchise on vice in their ward, collecting tribute from hundreds of establishments and using the revenue to maintain a political organization capable of delivering their ward's votes as a block to whichever mayoral or state candidate promised to leave their arrangements undisturbed.

The First Ward Ball, held annually from 1896 to 1908, was the most visible demonstration of this arrangement. Held in the Chicago Coliseum and attended by thousands of participants, the Ball mixed Chicago's political figures, including state legislators, city aldermen, and ward committeemen, with the city's most prominent gamblers, saloon keepers, and brothel operators. Admission was sold at prices that generated substantial revenue for the First Ward Democratic organization, and attendance by a vice operator was understood to be not entirely optional, a payment in social form of the tribute that was otherwise collected in cash. Reform newspapers covered the event with a combination of outrage and fascinated detail, and the Ball became a national symbol of the brazenness with which Chicago's political class conducted its relationship with criminal enterprise.

The durability of the Coughlin-Kenna arrangement demonstrated a characteristic that frustrated reformers consistently underestimated: the machine-crime relationship was not simply imposed from above on unwilling communities but was sustained by genuine constituency support from below. The First Ward included large numbers of working-class voters whose immediate economic interests were served by the machine's patronage operations, and who had little reason to support reform campaigns that might disrupt the services the machine provided. Reformers who imagined that exposing corruption would automatically generate popular opposition to the machine often found instead that immigrant and working-class voters preferred the corrupt machine that served them to the reform government that promised clean administration but typically cared little about their daily economic needs.

Corruption in Growing Cities

The corruption that sustained organized crime in American cities was not simply the product of individual dishonesty but a systemic feature of urban governance built into the structure of law enforcement, municipal administration, and political organization. Understanding corruption as a system, rather than as a collection of individual moral failures, is essential to understanding why reform movements so often achieved only temporary results, and why the same patterns of criminal-political cooperation recurred in city after city across the country.

Urban police forces in the late nineteenth and early twentieth centuries operated within an institutional structure that almost inevitably produced corruption. Police appointments were controlled by political machines, which meant that police officers owed their jobs to political figures who were themselves deeply embedded in the protection arrangements that sustained vice. Officers who did their jobs by enforcing laws against gambling and prostitution were not simply disrupting criminal enterprises; they were disrupting the revenue streams that sustained the political organizations to which they owed their employment. Officers who collected protection payments and turned a blind eye to vice were not aberrations in the system; they were functioning precisely as the system expected them to function.

The Lexow Committee hearings of 1894 provided the most detailed documentation of how this system worked in New York. Officers testified about the practice of "buying" positions: a promotion to police captain cost, by the testimony of various witnesses, between ten thousand and fifteen thousand dollars in the early 1890s, a sum that represented several years' salary for a working officer. This investment was expected to be recouped through the tribute collected from vice operators in the captain's precinct. Officers who did not collect this tribute not only failed to profit personally but found themselves at a competitive disadvantage relative to their colleagues who did, because the tribute was expected by the political figures above them in the hierarchy and failure to deliver it could jeopardize the officer's position.

The Structure of Police Corruption

Police corruption in this period was not disorganized bribery but a systematic institutional arrangement with its own rules, hierarchies, and expectations. Each level of the police organization had its own relationship with vice, its own expected share of the protection revenue, and its own political connections. The officer on the beat collected small amounts from street-level operations, the precinct captain collected larger amounts from the gambling houses and brothels in his territory, and figures higher in the hierarchy received percentages of the aggregate collected in their jurisdictions.

This systematic character meant that corruption was self-reinforcing. An honest officer who refused to participate in the system faced not only economic disadvantage but active career sabotage from corrupt colleagues and supervisors who saw non-participants as threats to the arrangement. Conversely, officers who participated deeply in the system had strong incentives to advance within it and to protect it from external challenge. Police opposition to reform movements was thus not simply a matter of individual officers protecting their personal income but of an organizational culture and structure that had evolved to sustain the corruption on which many careers and fortunes depended.

The corruption of the courts added another layer of protection for criminal enterprise. Judges in many cities were elected on tickets controlled by political machines, which meant that prosecutions of vice operators who had political protection were unlikely to result in conviction even when they resulted in arrest. Bail was set at levels that permitted continued operation pending trial. Cases were scheduled and rescheduled until witnesses lost interest or moved away. Charges were reduced or dismissed for technical reasons that courts with different political orientations would not have found compelling. The result was a justice system that functioned as a mechanism for the management of criminal enterprise rather than its suppression, processing arrests in ways that demonstrated the formal existence of law enforcement while ensuring that the enterprises generating protection revenue continued to operate.

Reform Movements and Their Limits

The decades between 1890 and 1920 saw recurring waves of reform activity aimed at disrupting the machine-crime relationship in American cities. The Progressive Era, roughly 1900 to 1917, produced a particularly intense burst of reform energy, including campaigns against vice, efforts to restructure municipal government through civil service reform and proportional representation, and investigative journalism that exposed the details of machine corruption to national audiences. Some of these campaigns achieved genuine results, at least temporarily: corrupt machine bosses were occasionally defeated, vice districts were sometimes closed, and police forces were periodically reorganized under more honest leadership.

But the structural limits of Progressive Era reform were significant and instructive. Reform movements were typically led by middle-class and upper-middle-class Americans whose relationship to the working-class and immigrant communities most affected by crime was distant and often condescending. Reformers tended to diagnose the problem of urban crime in moral and ethnic terms, attributing vice and gang activity to the supposed deficiencies of immigrant cultures rather than to the structural conditions of poverty, inequality, and political exclusion that actually produced them. This misdiagnosis led to reform programs that focused on moral uplift, the provision of settlement houses, temperance education, and Americanization programs, rather than on addressing the economic conditions that made criminal enterprise attractive.

Reformers also consistently underestimated the genuine services that political machines provided to their constituencies and the strength of working-class and immigrant loyalty to machine politicians who had served them. A Tammany ward boss who had provided coal in winter, secured employment for neighborhood residents, and produced bail money in emergencies commanded a real claim on voter loyalty that an honest reform candidate who had done none of these things could not easily displace. The machine-crime relationship was sustained not only by corruption but by a genuine exchange of services for loyalty that gave the machine a popular base reform movements found difficult to erode.

The limits of reform in this period had a paradoxical consequence for organized crime. When reform movements succeeded in closing vice districts, disrupting police protection arrangements, or convicting prominent criminal figures, they did not eliminate criminal enterprise but forced it to adapt. Criminal organizations that had operated openly under political protection learned to operate more covertly and more sophisticatedly. Operations that had been concentrated in specific districts dispersed into residential neighborhoods. Relationships with political figures became more subtle and less visible. The criminal organization that survived a successful reform campaign was typically more resilient, more organizationally sophisticated, and harder to attack than the one that had existed before the reform. In this sense, the reform movements of the Progressive Era, by disrupting but not destroying criminal enterprise, contributed to its professionalization in ways that bore fruit in the Prohibition era.

Everyday Life and the Criminal Underworld

The history of organized crime in American cities is not only a history of gang leaders, political bosses, and criminal entrepreneurs. It is also a history of the ordinary people who lived within and around the criminal economy: the runners who carried policy slips through immigrant neighborhoods, the bartenders who served drinks in saloons that hosted gambling operations, the women who worked in vice districts, the merchants who paid protection to avoid vandalism, and the residents of criminal-dominated neighborhoods who navigated the presence of gang organizations in their daily lives with a mixture of accommodation, avoidance, and occasional resistance.

For the young men who joined street gangs in immigrant neighborhoods, the decision to do so was rarely a simple choice between legitimate and criminal pathways. In most cases, the boundary between gang membership and ordinary neighborhood life was permeable and sometimes invisible. Gangs organized themselves around neighborhood social networks, and belonging to a gang in its lower levels often meant nothing more than hanging around with the same group of young men who had grown up together, shared school experiences, worked the same casual jobs, and attended the same church or synagogue. The escalation from neighborhood social grouping to criminal organization happened gradually, through specific opportunities and specific decisions, rather than through a single moment of crossing a clearly marked line.

The economic logic that drew young men into criminal activity was straightforward in an environment where legitimate employment was both scarce and brutal. A young man from an Italian or Jewish or Irish immigrant family in lower Manhattan in 1900 faced a labor market that offered, at best, factory work at wages of six or seven dollars a week for sixty or seventy hours of labor in dangerous, degrading conditions. The streets of his neighborhood offered, to those with the right connections and the right combination of nerve and judgment, substantially more: a runner for a policy operation might earn ten or fifteen dollars a week, enough to dress better than factory workers, to contribute meaningfully to the family economy, and to enjoy the social status that a little money and a lot of street presence could confer in a poor neighborhood.

Women and the Criminal Economy

The history of women in the criminal economy of this era is more difficult to recover because women were much less likely to appear in the court records, newspaper accounts, and police reports that form the primary documentary basis for the history of organized crime. Yet women were not absent from criminal enterprise; they occupied specific and often vulnerable positions within it.

The most visible and most discussed role of women in the criminal economy was as workers in vice districts. The women who worked in the brothels, lodging houses, and street-level prostitution operations of districts like the Levee and Storyville occupied positions of extreme vulnerability. They were typically paid a fraction of what their employers collected for their services, required to purchase food, clothing, and lodging from their employers at inflated prices, and subject to a variety of controls that limited their freedom of movement and their ability to leave their situations. The popular narrative of the era emphasized the figure of the innocent girl "lured" or "trafficked" into prostitution by criminal operators, and while trafficking did occur, the majority of women who worked in vice districts had entered more or less voluntarily, driven by economic desperation rather than physical compulsion. The distinction mattered less than reformers sometimes implied: desperation in an economy that offered women few alternatives to low-wage domestic or factory work was itself a form of coercion.

Women also appeared in the criminal economy as proprietors: madams who managed brothels, some of whom, like Ada and Minna Everleigh, achieved considerable wealth and a degree of power within the criminal world. Women ran policy operations in some neighborhoods, particularly in African American communities where the numbers game was a major industry. Women worked as fences for stolen goods, as organizers of shoplifting operations, and in various supportive roles within the organizational structures of criminal enterprises. Their contributions to criminal enterprise were consistently understated both in the contemporary accounts that shaped the historical record and in the subsequent histories that relied on those accounts.

African American Communities and the Criminal Economy

African American communities occupied a distinctive and particularly difficult position in the criminal economy of this era. In northern cities, Black communities were concentrated in specific neighborhoods by a combination of housing discrimination, economic exclusion, and the social dynamics of racial segregation, and criminal organizations operated within those communities in ways that both reflected and reinforced the broader structures of racial inequality in American society.

The policy game was especially important in African American communities in northern cities, where it operated as one of the few economic activities that could provide substantial income to Black entrepreneurs who were excluded from most legitimate business opportunities. Policy operators in Black neighborhoods built genuine organizational structures, employed runners and accountants and managers, and accumulated capital that was reinvested in community businesses, churches, and political organizations. The numbers banker was often a figure of real economic importance in Black neighborhoods, providing credit, employment, and political connections that the formal economy refused to extend to Black residents.

But African American criminal entrepreneurs operated under an additional layer of constraint and exploitation that white operators did not face. White criminal organizations that controlled particular criminal markets in the broader city frequently sought to extract tribute from or take over Black criminal operations, using both violence and political connections to impose their authority. Law enforcement, which was already corrupt and unreliable in its treatment of white criminal enterprises, was even more systematically hostile and exploitative in its approach to Black communities, where the police were an instrument of racial control as much as of criminal justice. The result was that Black criminal entrepreneurs faced all of the normal risks of operating in the illegal economy plus the additional risks of racial violence and racially discriminatory law enforcement.

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