Winning entrepreneurs in the shadow economy relied both on their connections to legitimate activities and on their ability to circumvent the law. Sometimes they obtained police cooperation with thoughtful bribes. More often, however, urban police struggled in good faith but in vain to thwart shady dealers and shut down their elusive operations. Police were faced with relatively small forces that had no hope of keeping up with exploding urban populations, increasing disparities of wealth, and a fiercely competitive labor market that led to chronic unemployment. These problems only encouraged underworld economies. Urban populations in large cities increased exponentially in the 19th century. Between 1830 and 1870, the populations of New York City, Philadelphia, Boston, Baltimore, and New Orleans each rose more than fourfold. Chicago, a mere backwater in 1830 (not even one of the 100 most populous cities) rose to become the fifth largest city in just four decades, supporting a population rapidly approaching 300,000.
Despite their unprecedented growth, cities were slow to give up their night watchmen, informal groups of private citizens who had little training in law enforcement. And when they established municipal police forces, the numbers of uniformed men did not grow to meet cities’ needs. Low-rent districts, most often found at the edges of city centers and along waterfronts, were frequently the vice districts too, attracting brothels, gambling halls, pawnshops, and illegal gin shops. Self-sustaining cultures within the larger environs, they continued to thrive, despite the attention they received from police.