Encyclopedia of Greater Philadelphia

Annie Anderson

Prisons and Jails

In the late 1700s, on the heels of the American Revolution, Philadelphia emerged as a national and international leader in prison reform and the transformation of criminal justice practices. More than any other community in early America, Philadelphia invested heavily in the intellectual and physical reconstruction of penal philosophies, and the region’s jails and prisons reflected these evolving principles. Throughout the 1800s, global and local observers looked to Philadelphia—particularly the Pennsylvania system of solitary confinement pioneered at Eastern State Penitentiary—as they modeled penal practices in their communities. By the late twentieth century, however, Philadelphia led the nation not in reform, but in rates of incarceration.

[caption id="attachment_29555" align="alignright" width="196"]a membership certificate for the Pennsylvania Prison Society. Top half is dominated by a vignette portrait of Bishop William White. Below the portrait is an illustration of Eastern State Penitentiary, a prison complex of eight long halls connected to a central hub. The building is surrounded by a stone wall. This Pennsylvania Prison Society membership certificate from 1855 features Eastern State Penitentiary and describes the innovative Pennsylvania System of Prison Discipline, a strict solitary confinement system advocated by the society. (Library Company of Pennsylvania)[/caption]

Local holding and correctional facilities—jails—emerged as the colonies’ populations grew and local economies developed. Philadelphia erected its first jail—essentially a well-fortified box-like room, seven feet by five feet—in late 1682 or early 1683 at the corner of Second and High (Market) Streets. Officials constructed a succession of several small jails in the near vicinity over the next forty years, including a brick prison, fourteen feet wide and twenty feet long, on High Street in 1695. A keeper lived in half of the building. A few years later, it was deemed inadequate. Around 1720, a stone prison and workhouse opened nearby on the corner of Third and High Streets. The prison portion of this facility housed debtors, runaway apprentices, and untried prisoners. The workhouse held those convicted of theft, vagrancy, and disorder.

Still, incarceration was used sparingly in colonial America. While criminal codes called for imprisonment for crimes such as bigamy and dueling, incarceration was typically reserved for those awaiting trial or sentencing. Penalties for those found guilty included fines or restitution, or corporal punishments such as branding or whipping. Capital punishment was meted out for a range of crimes, including blasphemy, kidnapping, and rape. As the colonies and their populations grew, officials made use of forts and blockhouses to house lawbreakers.

In Pennsylvania, William Penn (1644–1718) ushered in new legislation that reflected his Quaker values, including an almost total disavowal of capital punishment. In 1682, the province of Pennsylvania banned the death penalty for all crimes except murder and treason, while other colonies that emerged in the same era continued to enact much stricter criminal codes. Though Penn’s 1682 body of laws, known as the “Great Law,” included fewer capital offenses, it still demanded shameful corporal punishments and prison time: stealing livestock warranted thirty-nine lashes and banishment; swearing merited five shillings or five days in jail; sodomy and bestiality cost the forfeiture of one-third of one’s estate, whipping, and six months in the house of correction.

West Jersey Mirrors Pennsylvania

Criminal codes in the colonial province of Quaker-dominated West Jersey mirrored the milder punishments enacted in Pennsylvania, which varied sharply from the rigid codes of Puritanical East Jersey and New England. In West Jersey, criminal law protected the accused from undue punishments: no accused person could be convicted except by a jury of his neighbors, the accused could reject as many as thirty-five jurors before going to trial, and conviction could only occur upon the sworn testimony of two reputable witnesses. Still, corporal acts—whether the death penalty, branding, or whipping—encompassed nearly all punishments in East and West Jersey, which merged into a unified New Jersey in 1702. Because of the predilection for physical punishments, New Jersey had little need for penal institutions beyond small local jails, and there was no central prison administration during the colonial era.

[caption id="attachment_29554" align="alignright" width="300"]A black and white illustration of Walnut Street Prison Walnut Street served many purposes across multiple sectors of government during its six decades. From its opening in 1776 until it closed in 1835, Walnut Street Jail operated as the county jail of Philadelphia. From 1790 until 1818, it also operated as Pennsylvania's only state prison. (Library of Congress)[/caption]

Overcrowding, corruption, violence, and bribery ran rampant in Philadelphia’s early jails. The stone prison earned the nickname “school for crime” and “seminary of vice.” Administrative control of the jail rested with the local sheriff, who extorted money from prisoners, sold liquor from a well-stocked bar, and withheld food and other necessary goods. Individuals—regardless of sex, age, or crime committed—mingled indiscriminately. Officials ordered the building of a new facility in 1773, and this “New Gaol,” known as the Walnut Street Jail, opened in 1776. The old stone jail closed in 1784 and was demolished the following year. Despite the larger quarters, the Walnut Street Jail hosted the same debauchery as previous jails. (The jail keeper operated a tavern in his previous job.) A 1787 grand jury reported that “the prison seems to them to be open, as to the general intercourse between the criminals of the different sexes; and that there is not even the appearance of decency.” Scandals plagued other local jails. Chester County’s house of correction, opened around 1725, was neglected within a few decades of its opening. An applicant for the position of jail keeper wrote: “the person last appointed [keeper] . . . having absconded from his residence therein . . . the workhouse has for a considerable time past been very ill kept.” Even as jails became attached to county courthouses—public facilities charged with the high-minded task of facilitating justice—the improprieties of local houses of correction continued into the 1800s. In 1888, the New Jersey State Board of Health condemned the Camden County Jail “as a disgrace to our common civilization and a menace to the health of the people.”

Prompted by the scandals of vice-ridden jails and the inhumanities of public punishment and spurred on by post-Enlightenment thinkers such as British prison reformer John Howard (1726–90), a group of prominent citizens formed the Philadelphia Society for Alleviating the Miseries of Public Prisons (later renamed the Pennsylvania Prison Society) in 1787. The group, comprised of thirty-seven individuals from the city’s elite civic and political circles, including physician Benjamin Rush (1746–1813), politician Tench Coxe (1755–1824), statesman Benjamin Franklin (1706–90), and Episcopal bishop William White (1748–1836), advocated for prisoners’ rights, as well as the restructuring of correctional spaces. The Prison Society shunned a corrupt criminal legal system and grotesque public punishments in favor of a rational, humanistic—and newly private—correction of the spirit. The group drew on Howard’s ideas that safe and decent jail spaces—and thus, true rehabilitation—could only be ensured by segregation of individuals by class of offense. In April 1790, the society’s lobbying paid off: a new law mandated solitary confinement at the Walnut Street Jail and called for the erection of a new “penitentiary house” at the jail for “the purpose of confining therein the more hardened and atrocious offenders.”

Walnut Street Prison, the Country’s First

With this new law, the Walnut Street Jail became the Walnut Street Prison—the country’s first state prison. With this designation, the distinction between a jail and a prison became clearer: jails came to house individuals awaiting trial or sentencing, along with those convicted of misdemeanors, minor offenses that typically carry a sentence of one year or less, while prisons house individuals convicted of felonies, more serious crimes that demand longer sentences. The Walnut Street Prison incarcerated convicted offenders from every part of the commonwealth of Pennsylvania—a practice never before attempted in the fledgling United States. New Jersey soon followed suit. It began construction on its first state prison, in Trenton, in 1797 and opened it in 1799. The inscription over its front door read, in part: LABOR, SILENCE, PENITENCE, THIS PENITENTIARY HOUSE . . . THAT THOSE WHO ARE FEARED FOR THEIR CRIMES MAY LEARN TO FEAR THE LAWS AND BE USEFUL. Delaware did not establish a state penal facility until well into the twentieth century, opting instead to send adult offenders to county facilities. Though some regional correctional philosophies emerged, consistent penal practices across the colonies and in the early republic remained elusive.

[caption id="attachment_29550" align="alignright" width="200"]a color photograph of a prison cell with paint and plaster falling off of the wall and collects on the ground. There is a badly decayed chair, table, and stool. Above, light shines through a narrow slit-shaped sky light. Eastern State Penitentiary’s vaulted ceilings and skylights were strategically designed to invoke a churchlike atmosphere. Eastern State was the first prison to practice solitary confinement on a large scale, and it introduced the concept of “penitence,” or true regret, as a penal philosophy. (Photograph by M. Fischetti for Visit Philadelphia)[/caption]

Untidy and experimental at first, Philadelphia’s prisons nearly perfected the separation of individuals in jails and prisons based on sex, age, and type of offense by the 1820s. The early experiment of solitary confinement at Walnut Street Jail inspired them to push for a prison where this penal practice could be implemented on a large scale. The first such prison, Eastern State Penitentiary admitted its first prisoner, Charles Williams (b. ca. 1809), in October 1829. Eastern State’s founders believed that in isolation, prisoners would reflect on their crimes and grow penitent; access their inner goodness and shun future criminal activity; and cease to corrupt or be corrupted by criminal associations in overcrowded jails. Prisoners spent twenty-three hours a day alone in their cells; they had two half-hour breaks for outdoor exercise in small yards attached to each cell. Prisoners ate, slept, and labored in their cells. Though internationally admired for its novel design and methodology, Eastern State’s use of solitary confinement drew criticism almost immediately after the prison opened. The British author Charles Dickens (1812–70), who visited Eastern State in 1842, claimed that prolonged isolation would inspire troubling mental health consequences. Outside observers found evidence of psychosis, anxiety, and depression among the prison population, but Eastern State officials remained vigilantly committed to the solitary system, at least publicly.

Eastern State’s architect, John Haviland (1792–1852), and the prison’s Quaker exponents wielded wide regional influence. Haviland was drafted to design New Jersey’s second state prison in Trenton, which opened in 1836. Built on a radial plan, it also imposed the Pennsylvania system of solitary confinement. In Philadelphia, Moyamensing, the county facility at Eleventh and East Passyunk Avenue built to replace the Walnut Street Prison, also employed the Pennsylvania system of separate and solitary confinement—in its case, for individuals awaiting trial, along with those serving short sentences. Moyamensing remained the major hub for those facing and serving misdemeanor charges from its opening in 1835 until a second county facility, Holmesburg, opened in 1896. While Moyamensing remained open until 1963, Holmesburg, in northeast Philadelphia, remained open until 1995. Built as a solitary confinement prison, Holmesburg’s radial plan and castlelike stone walls mirrored Eastern State’s architectural aesthetic. Like Moyamensing, it held men and women who were awaiting trial or serving short sentences. As county facilities, Moyamensing’s and Holmesburg’s populations were more transient—though larger, in terms of sheer numbers—than the convicted felony population of Eastern State.

Abandoning Solitary Confinement

Eastern State did not officially abandon the philosophy of solitary confinement until 1913—more a veneer at that point—when prisoners were allowed to congregate for worship, sports, and other activities. Overcrowding forced the eventual construction of eight additional cellblocks, wedged between existing structures on the prison’s ten-acre plot of land. Outdated and expensive, Eastern State closed in 1970, and most prisoners were transferred to Graterford, in Montgomery County, which was built largely by prison labor and opened in the late 1920s as Eastern State’s “farm branch.”

[caption id="attachment_29556" align="alignright" width="300"]a black and white aerial photograph of Holmsburg Prison. It has ten wings connected in a radial pattern to a central hub and is surrounded by a wall. Holmesburg Prison opened in 1896 in northeast Philadelphia and operated until 1995 and was beleaguered by skirmishes, power struggles, and violence throughout its history. Despite shuttering in 1995 and years of architectural decrepitude, Philadelphia officials used Holmesburg to house overflow prisoners as recently as 2013. (PhillyHistory.org)[/caption]

In the mid-twentieth century, after American prisons moved to congregate models, Philadelphia became known for its diagnostic and classification services. In the 1950s, state prison systems became more professionalized, with formal guard trainings and new correctional entities; Pennsylvania established the Bureau of Corrections in 1953, and Delaware created the State Board of Corrections in 1956. Beginning in the early 1970s, the national prison population grew steadily due to a series of policy decisions: longer prison sentences and mandatory minimums, new laws and enforcement techniques, and increased reliance on prisons as a punishment for all crimes.

From 1790 to 1970, Philadelphia was home to a state prison and was known as the most important locality of penal pioneering in the country. The landscape of prisons changed drastically over the course of those centuries—and in the years that followed. Because of increased incarceration rates, the number of state prisons in Pennsylvania grew from seven in 1970 to twenty-four in 2017. By the early twenty-first century, the state was also home to dozens of additional local jails, federal prisons, and immigrant detention facilities. Many Pennsylvania prisons and jails operated over their capacity. To ease overcrowded conditions, advocates lobbied for a range of reforms: more lenient sentences, the end of cash bail, and modernized facilities.

By 2015, the era of mass incarceration had prompted a bipartisan coalition of legislators to push for sentencing reform and the reduction of the prison population. Yet in 2017 the United States continued to have the highest incarceration rate in the world—with 25 percent of the world’s prisoners but just 5 percent of the world’s population. Once a trailblazer in prison reform, a pioneer in both prison architecture and philosophy, by 2017 Philadelphia had the highest incarceration rate of any large jurisdiction in the country, with about 810 per 100,000 people in jail—making it one of the most incarcerated places in the world.

Annie Anderson is the manager of research and public programming at Eastern State Penitentiary Historic Site and the coauthor, with John Binder, of Philadelphia Organized Crime in the 1920s and 1930s (Arcadia Publishing, 2014). She received her M.A. in American Studies from the University of Massachusetts Boston.


[caption id="attachment_23359" align="alignright" width="254"]Black and white photograph overlooking Thirteenth Street with the Hotel Vendig in the foreground and the old Reading Terminal right center. The Delaware River is visible in the distance. A large section of the Philadelphia’s vice district—known as the “Tenderloin”—is visible in this 1915 photograph, looking east from City Hall tower. At center is massive Reading Terminal, whose completion in 1893 fueled mobility and helped set the stage for a transient population that was a hallmark of the Tenderloin. (PhillyHistory.org)[/caption]

In the final decades of the 1800s, a vice district emerged just north of Philadelphia’s city center. Bound by Sixth Street on the east, Thirteenth Street on the west, Race Street to the south, and Callowhill Street to the north, this neighborhood was called the Tenderloin, like similar districts in many other cities of the era. The Tenderloin, encompassing Philadelphia’s cheap amusements district as well as its tiny Chinatown, housed as many as 250 pool rooms, gambling resorts, saloons, opium dens, and brothels by the close of the nineteenth century.

The origin of the nickname “Tenderloin” is unclear, but newspaper articles from the late 1800s note that red-light districts—areas with concentrated commercial sex and vice enterprises—offered “prime cuts” for multiple constituencies: sex, drugs, and amusements for the working classes; good incomes for madams, pimps, and showmen; and graft opportunities galore for politicians and police officers.

As in other cities, Philadelphia’s Tenderloin developed at the edge of the growing central business district (then extending westward along the axis of East Market Street) and in the vicinity of new railroad stations (the major depot for the Philadelphia and Reading Railroad built in 1859 at Broad and Callowhill Streets and its replacement, Reading Terminal, on Twelfth Street between Arch and Market, in 1893). The shifting market functions of the city center produced change for the neighborhood once occupied by prosperous merchants. As the railroads made it possible for the professional classes to move to suburbs like Chestnut Hill and the Main Line, the district they left behind became home to wholesale and retail warehouses, tenements, stores, single-family houses, and furnished-room houses (high-density homes offering lodging to single people). An abundance of inexpensive housing attracted a new population of working-class Chinese and European immigrants as well as African Americans. Low rents and the proximity to the railroad depots created a venue for vice as well as quick access for visitors to the district’s dime museums, brothels, and vaudeville shows.

Tenderloin Amusements

[caption id="attachment_23361" align="alignright" width="275"]Illustration of the facade of a large, four story building with people on the sidewalk out front and entering the building. The words "B.F. Keith's Bijou Theater" are written above the large entryway. The Bijou Theater–depicted in this 1922 illustration–was part of the B.F. Keith Circuit, a chain of vaudeville houses owned by Benjamin Franklin Keith and Edward Franklin Albee II. (Library Company of Philadelphia)[/caption]

The Tenderloin’s more unseemly offerings sprang up next to the district’s working-class entertainment options: minstrel shows, dance halls, and circus performances. On one block of Eighth Street, between Arch and Vine, three vaudeville theaters—including the Bijou and the Fourpaughs—emerged between 1875 and 1895. By 1910, this block contained five movie houses (in addition to the three vaudeville theaters), two dime museums, five shooting galleries for recreational target practice, and numerous other cheap diversions like penny peep shows and palm-reading parlors. A sociologist who surveyed the Tenderloin reported in 1912: “The tenderloin theatres are not composed entirely of degenerate residents of the slums, of wicked gamblers, of ‘furnished roomers,’ and painted blondes of doubtful virtue.” He conjectured that without the patronage of people passing through the city and others visiting from the suburbs and country, more than half of the Tenderloin’s theaters would fail. He also pointed to the district’s inexpensive housing stock, a plethora of low-cost rooming houses that furnished chorus girls and actors with temporary shelter and board.

The eastern outskirts of the Tenderloin and the warehouse district stretching east to the Delaware River attracted a Skid Row population of poor, homeless, and transient men and the missions, saloons, flophouses, and cheap restaurants that catered to them. This population, like the working classes, was drawn to the Tenderloin because of its inexpensive housing options and its proximity to the city’s rail yards and labor opportunities.

[caption id="attachment_23787" align="alignright" width="233"]Hand-drawn map depicting a section of the city from about a half block below Arch Street to a half block above Spring Garden and from 4th Street on the east to about a half block west of 11th. The map also marks the locations of hotels, bars, theaters, missions, and liquor stores as well as two large areas slated for redevelopment to the north and east. Go to the image gallery at right for a larger view of this map, which comes from a 1952 report titled “What About Philadelphia’s Skid Row?: A Report on Homeless and Transient Men Living in the Vicinity of 8th and Pine Streets.” (Special Collections Research Center, Temple University Libraries)[/caption]

The abuse of opium, morphine, and cocaine ran rampant in the Tenderloin. By 1910, Americans consumed 68,000 pounds of opium annually, with many of the nation’s Chinatown neighborhoods facilitating the drug’s trade. The recreational use of opium had existed in China for centuries, and many Chinese immigrants brought a tradition of opium smoking with them when they arrived in the United States. Chinese immigrants settled the 900 block of Race Street in the 1870s and 1880s. The concurrent emergence of the Tenderloin around Chinatown ensured that opium dens catering to a Chinese clientele found new patrons of differing ethnic and racial backgrounds. During one midnight raid on Chinatown's opium dens in 1900, Philadelphia police arrested more than forty Chinese-Americans, along with white and black men and women.

The Politics of Vice

Though police disrupted illegal activity in the Tenderloin, the press noted a pattern of inconsistent law enforcement in the district. Newspapers and reformers had long observed connections between the city’s political machine and its most well-known vice district. In a 1905 editorial in the Philadelphia Inquirer, the Rev. Daniel I. McDermott, rector of St. Mary’s Roman Catholic Church, claimed that the machine had “made a Sodom out of the heart of the city” by regulating vice in the Tenderloin. Many of the district’s “dens of infamy” remained operational by bribing local police officers and paying tribute to the Republican political syndicate. McDermott chided the police and the mayor, asking what right they had to “dedicate a section of the city to debauchery, to make it a plague spot, to scandalize its residents, to imperil the virtue of its youth and depreciate the value of property.” A grand jury investigating the Tenderloin echoed McDermott’s sentiments and went even further, blaming the prevalence of “disorderly houses” (brothels) not only on police graft and political interference, but also on the leniency of the courts. Many prostitutes simply saw their court fines as licensing fees.

To attack the social evils of the Tenderloin, reformers sought to dismantle the Republican political apparatus from the top down. They rallied around Rudolph Blankenburg (1843-1918), who became mayor of Philadelphia in 1911 after what the New York Times later called “one of the greatest reform campaigns ever fought in this country.” Blankenburg—a rarity as a reform-minded Republican within a then-unscrupulous party—appointed a Vice Commission, which uncovered a thriving market throughout the city for commercial sex, gambling, and drug use. The investigators found the largest number of vice houses in the Tenderloin (the city’s sixth and eighth police districts), which accounted for much of the $6.2 million spent on prostitution per year in Philadelphia. Three-quarters of all the city’s arrests for streetwalking (prostitution solicitation in the streets) took place in the Tenderloin.

[caption id="attachment_23242" align="alignright" width="249"]Photograph of Rudolph Blankenburg Rudolph Blankenburg became mayor of Philadelphia in 1912 after what the New York Times later called “one of the greatest reform campaigns ever fought in this country.” (Historical Society of Pennsylvania)[/caption]

Like other Progressive-era reformers, Blankenburg believed vice to be a social evil requiring treatment similar to contagious diseases. The social contamination caused by vice, they reasoned, required quarantine and suppression. This segregationist approach to vice differed from two other common approaches to combating vice in this era—the first involved licensing and regulation, while the other, referred to as “abolition,” required constant repression until annihilation was achieved.

Although Blankenburg may have leaned toward a segregationist approach, neither he nor the Vice Commission considered the Tenderloin to be a segregated district because respectable people lived and worked throughout the district despite the presence of vice. Just north of the Tenderloin sat the furnished-room district, home to a burgeoning class of office workers—many of whom traversed the Tenderloin every day on their way to and from work in Center City. If not entirely segregated, the Tenderloin occupied the space of de facto red-light district in the city’s popular imagination, thanks to regular media coverage of the district’s seamy character.

The Tenderloin became a site of spectacular police raids, open-air political stumping, and missionary moralizing. In 1910, more than fifteen hundred religious reformers marched into the Tenderloin from City Hall on a Saturday evening, intent on interrupting the vice trade and focusing press attention on the city’s underbelly. In the wake of the 1913 Vice Commission’s investigation, Mayor Blankenburg took a walking tour of the Tenderloin, and within the span of four blocks, hundreds of onlookers had joined him for an excursion through the neighborhood. Although Blankenburg declared in 1912 that vice was “practically eliminated” in the city, and again in 1915 that “the much-heralded ‘Tenderloin’ does not exist,” vice squads continued to locate and interrupt illegal activity. During a single night in July 1916, police arrested more than five hundred people. Critics claimed that highly publicized raids and marches drew unnecessary attention to the red-light district while at the same time displacing vice onto other neighborhoods. 

The Decline

[caption id="attachment_23364" align="alignright" width="275"]Black and white photograph of the facade of a white building with several banners draped above the entrance. Two signs at either side of the entrance advertise "The French Frolics." Visitors to the Tenderloin viewed minstrel and vaudeville shows, motion pictures, and burlesque performances at the Trocadero, shown in this 1917 photograph. (PhillyHistory.org)[/caption]

As in many other red-light districts across the country, the Tenderloin’s sex trade declined around 1920. The United States’ entrance into World War I in 1917 introduced a marked national effort to repress vice and promote healthy living among servicemen. Police clamped down on districts like the Tenderloin, and in Philadelphia vice migrated to the main commercial thoroughfare, Market Street, where department stores and motion picture houses drew men and women from a variety of backgrounds for work and pleasure. Changing gender norms, economic opportunities, and the massive federal apparatus of Prohibition also shifted the landscape of vice by pushing drinking culture and its attendant behaviors further underground.

Architectural interventions further disrupted the neighborhood’s identity. The 1926 opening of the Delaware River Bridge (later renamed the Benjamin Franklin Bridge) led to more traffic around Franklin Square—the eastern boundary of the Tenderloin. By the mid-1900s, as commercialized vice disappeared from all but a few pockets of the Tenderloin, the former red-light district became known as Skid Row, as a longstanding homeless population continued to inhabit the neighborhood. The late-twentieth-century building of the Vine Street Expressway through the exact center of the former Tenderloin shifted the character of the Skid Row and Chinatown neighborhoods even more. A destination for pleasure seekers and a home to many working-class people in the late 1800s and early 1900s, the former Tenderloin became simply a place for commuters to pass through on their way elsewhere.

Annie Anderson is the senior research and public programming specialist at Eastern State Penitentiary and the coauthor, with John Binder, of Philadelphia Organized Crime in the 1920s and 1930s (Arcadia Publishing, 2014). She received her M.A. in American Studies from the University of Massachusetts Boston.


Bootleg liquor, produced illegally during Prohibition (1920-33), flowed into the Philadelphia region from a variety of sources, including overseas shipments, small home stills, large stills in urban factories and country barns, beer breweries, and manufacturers of industrial alcohol. Philadelphia’s location at the confluence of the Delaware and Schuylkill Rivers, just inland from the Atlantic Ocean, enabled deliveries of alcohol on ships from Canada, Europe, and the Caribbean. Trucks hauled imported liquor from coastal New Jersey towns like Atlantic City inland to Camden and Philadelphia, while beer arrived on trains from rural locales like Berks County.

[caption id="attachment_17004" align="alignright" width="300"]An Internal Revenue Service (IRS) agent scrutinizes the contents of a moonshine still during the Prohibition era. An Internal Revenue Service agent scrutinizes the contents of a moonshine still during the Prohibition era. (Library of Congress)[/caption]

Bootlegging gained protected status in a region where neighborhood saloons often served as informal offices for local ward bosses. Corrupt politicians, many operating within the Republican machine, worked in concert with police captains to protect vice industries like prostitution and bootlegging. Police heads often received kickbacks from both their underlings—for job protection—and from the illegal entities in their district—for ignoring their illicit operations.

Just before Prohibition took effect, Philadelphia was home to 1,700 saloons. Nearly a decade later, investigators estimated that nearly 1,200 saloons still operated more or less openly. Philadelphians abided a city of speakeasies, patronizing the candy stores, barber shops, pool halls, and private residences that served illegal liquor. The multitude of breweries in Philadelphia, which had an extensive and centuries-old history of beer production, also continued to supply the region.

Risks of Bootleg Liquor

While police guessed that 8,000 unlicensed taverns operated throughout the city, journalists estimated that at least 8,000 more “blind tigers” sold intoxicants to Philadelphians. Imbibing bootleg liquor carried risk; over the course of one month in 1923, Philadelphia reported 307 alcohol-poisoning deaths to the federal Prohibition Bureau. Government chemists noted that most of their confiscated bootleg liquor samples contained wood alcohol, chloride, sulfuric acid, iodine, or some other poison. By the late 1920s, temperance forces in the government ramped up their anti-liquor crusade by introducing a formula that doubled the poison in denatured industrial alcohol. Imbibing a product redistilled improperly by amateur moonshiners, consumers ran the risk of blindness and death. Nonetheless, forty million dollars poured through Philadelphia’s liquor trade annually.

The Delaware Valley, a hub of the chemical industry, produced millions of gallons of industrial alcohol. Those holding federal permits to manufacture perfumes, medicines, and barber supplies received about 430,000 gallons of alcohol every month. Many of these permit-holders operated “coverup houses” that distributed alcohol to consumers. Investigators unearthed records detailing implausibly large deliveries of hair tonics and perfumes throughout the Philadelphia region, including a delivery of 500 gallons of “hair oil” to an unidentified town of just fifty people. From 1924 to 1928, the number of gallons of industrial alcohol released in Philadelphia doubled, from five million to ten million. 

As Philadelphia’s industrial alcohol purveyors moved their product over land, high-profile rum-runners like Bill McCoy (1877-1948) set up shop in the Quaker City, moving their liquor into the city via its waterways. Bootleg liquor bound for Philadelphia often ran first through Atlantic City, described as a “smugglers’ paradise” because of the cooperation among rum-runners, local politicians, and Coast Guard officials. Rum-runners ushered as many as ten million quarts of liquor per year through the Bahamas and up the Atlantic Coast. McCoy and others sailed “Rum Row,” an Atlantic Ocean corridor stretching from Atlantic City to New York’s Long Island, making sure to stay outside of U.S. maritime limits (or working with corrupt Coast Guard officers) as they brought bootleg shipments northward. Though the term “the real McCoy” emerged in an earlier era, it was used by McCoy’s biographer in 1931 to signal the bootlegger’s unadulterated product: high-quality, single-source imported liquor.

The Regional Network

[caption id="attachment_17005" align="alignright" width="245"]Bootlegger and boxing promoter Max "Boo Boo" Hoff's speakeasy, the 21 Club, at the corner of Juniper and Locust Streets. Bootlegger and boxing promoter Max "Boo Boo" Hoff ran a speakeasy, The 21 Club, out of this castlelike building at the corner of Juniper and Locust Streets. (PhillyHistory.org)[/caption]

Numerous bootlegging gangs serviced the city alongside Philadelphia’s bootlegging kings, Max “Boo Boo” Hoff (liquor) (1895-1941) and Mickey Duffy (beer) (1888-1931). Philadelphia bootleggers worked in concert with South Jersey syndicates, who in turn partnered with North Jersey and New York City operatives. Max Hassel (1900-33), a bootlegger from Reading, Pennsylvania, who owned more than a dozen breweries in Pennsylvania, New York State, and New Jersey, paired with Duffy to operate several beer breweries in South Jersey, including Camden County Breweries Inc. and Camden County Cereal Beverage Company. Hassel also worked with Irving Wexler (1888-1952), commonly known as Waxey Gordon, a prominent bootlegger and associate of New York City crime kingpin Arnold Rothstein (1882-1928).

Philadelphia’s bootleg trade depended on the region’s roads, rail routes, and waterways—its interconnectivity and proximity to other import and export hubs, like Trenton, New Jersey, and Wilmington, Delaware. Bootleg business that affected Philadelphia often affected the surrounding region. When investigators probed bootleggers and racketeers in Philadelphia during the 1928 Special August Grand Jury investigation, some illicit entities crossed the Delaware River to Camden, New Jersey; as Philadelphia became more temperate, Camden became less so.

Charged with investigating bootlegging and its attendant gang violence, the 1928 Special August Grand Jury revealed the extent to which illegal liquor saturated the region, putting bootleggers on the defensive. The grand jury found that over the course of a few months, in excess of a million gallons of consumable liquor was released into the city, much of it diverted from denatured industrial alcohol. Philadelphia boxing promoter and nightclub owner Max Hoff built a bootlegging empire from industrial alcohol and amassed a fortune. Hoff operated several financial firms, including the Franklin Mortgage & Investment Co., to manage the revenue from his bootlegging ventures.

Despite interviewing 748 witnesses, the grand jury failed to indict Hoff or any other big-name bootlegger. Its success lay in uncovering police graft. When the grand jury finished its work, 138 police officers were deemed unfit for service. Many of these officers worked within Unit No. 1, an elite vice force established in 1924 by Director of Public Safety Smedley Butler (1881-1940).

[caption id="attachment_17003" align="alignright" width="300"]The Bailey Brothers bootlegging gang Brothers Francis Bailey (far left) and Harry Bailey (far right) flank the members of their bootlegging gang: Louis "Fats" Barrish, Peter Ford, George "Skinny" Barrow, and Robert Mais. (Philadelphia City Archives)[/caption]

In its report, the grand jury admitted it failed to destroy an underworld architecture built on bootlegging. In noting the lack of a permanent solution to the liquor racket problem, it implicated the residents of Philadelphia. It reasoned that only a constantly vigilant citizenry could prevent bootlegging, violence, and police graft. District Attorney John Monaghan (1870-1954), leading the investigation, implored Philadelphians to insist upon clean government and law and order. His exhortation echoed the voices of many Pennsylvania reformers of the 1920s, including Butler and Governor Gifford Pinchot (1865-1946). The will of Philadelphians to abide by Prohibition remained limited, however, and officials who zealously enforced the unpopular federal mandate assumed a hefty political liability. Bootlegging in Philadelphia continued until Prohibition’s repeal, meeting the unwavering demand for liquor.

Annie Anderson is the senior research and public programming specialist at Eastern State Penitentiary and the co-author, with John Binder, of Philadelphia Organized Crime in the 1920s and 1930s (Arcadia Publishing, 2014). She received her M.A. in American Studies from the University of Massachusetts Boston.


Despite the national prohibition of alcohol from 1920 to 1933, Philadelphia earned a reputation rivaling Chicago, Detroit, and New York City as a liquor-saturated municipality. The Literary Digest described Pennsylvania as a "bootlegger's Elysium," with every city as "wet as the Atlantic Ocean." The Quaker City in particular was singled out, by newspapers from New Haven to Newark, as one of the wettest and wickedest cities in the United States. Philadelphia and Atlantic City, New Jersey, a seaside resort town that served as a major port of entry for illegal liquor, were considered “open towns” during Prohibition—open in their defiance of liquor laws. 

[caption id="attachment_16459" align="alignright" width="225"]General Smedley Butler destroying a keg of beer with an axe Philadelphia received help from the federal government twice in the 1920s to combat its Prohibition-fueled crime problem. The first intervention involved the appointment of General Smedley Butler (1881-1940), shown here in 1924 destroying a barrel of beer. (Library of Congress)[/caption]

Prohibition began in 1919 with the passage of the Eighteenth Amendment, which made the production, transportation, and sale of alcohol illegal. Although the Eighteenth Amendment took effect nationally in 1920, several states enacted prohibition before then, including Delaware on March 18, 1918, and Pennsylvania on February 25, 1919. New Jersey ratified the Eighteenth Amendment on March 9, 1922. A confluence of social forces brought Prohibition to the national stage after nearly a century of Protestant criticism aimed at the supposed moral laxity induced by alcohol. In the early 1900s, the United States saw a rise in xenophobia against immigrants whom nativists associated with alcohol—especially those of Irish and German descent. Factions of the women’s suffrage movement propped up their claims to full citizenship by proclaiming a distinctly feminine moral authority, guided by temperance. Advocates of clean government and clean living argued that the elimination of the saloon would promote moral character and curtail the power that political bosses held. Prohibition encapsulated the Progressive Era’s impulse toward reform.

Though drinking moved underground with the introduction of Prohibition, Philadelphians actually had more saloons and watering holes to choose from after the law was enacted. The supposed abolition of bars and liquor dispensaries allowed for the emergence of a black market economy regulated only by bootleggers. Journalists reported that Pennsylvania’s largest cities, including Pittsburgh, Harrisburg, and Scranton, showed no pretense of obeying the Prohibition laws. Philadelphia, meanwhile, was the worst Prohibition violator in the Commonwealth, allowing its citizens considerable ease and freedom to obtain intoxicating beverages. Philadelphia had long been one of the nation’s leading beer brewing capitals. Though some breweries switched to making “near beer” (a malt beverage with an alcohol content of less than 0.5%) and soft drinks during Prohibition, many continued brewing beer. Philadelphia police suspected and pounced on the illegal activity. Vice raids on dozens of brewers—including Esslinger & Son, Finkenauer Brewing Co., Liebert & Obert, Roehm Brewing Co., and Philadelphia Brewing Co.—turned up high-powered beer. Most Philadelphia breweries failed or were padlocked out of existence by the early 1930s. A city of nearly 100 breweries in the 1880s, Philadelphia had just 10 licensed breweries when Prohibition ended in 1933.

A Cyclical Pattern of Corruption

A city of two million residents, Philadelphia accommodated as many as 16,000 speakeasies during Prohibition. City officials, public servants, bootleggers, and consumers contributed to a cyclical pattern of corruption around the management and distribution of vice. Long before Prohibition, the Republican political machine used the police as a central tool in maintaining control over the city’s various districts. Philadelphia police officers, many taking bribes from bootleggers, prostitution houses, and other illegal entities, contributed to corrupt ward politicians who hand-picked police captains and provided job protection. One policeman estimated that politicians took one day’s pay per month from each of the 7,000 men employed as police officers and firefighters. While Prohibition did not invent corruption among political and law enforcement entities in Philadelphia, it exacerbated established patterns of misconduct. As the 1920s wore on, bootlegging gangs wreaked violent havoc on the city, while officials took a cut of their profits. In describing the Quaker City’s entrenched machine politics and lax law enforcement, journalists resurrected the nickname “corrupt and contented,” first used by Lincoln Steffens in 1903.

[caption id="attachment_16461" align="alignright" width="300"]Police testing a new speedboat in 1925. Smedley Butler’s tenacity in pursuing Prohibition violators extended to the waterfront, patrolled by a new police speedboat obtained at Butler’s direction and seen here during a test trip in 1925. (Special Collections Research Center, Temple University Libraries)[/caption]

Philadelphia received help from the federal government twice in the 1920s to combat its Prohibition-fueled crime problem. The first intervention involved the appointment of General Smedley Butler (1881-1940), a decorated Marine, as director of public safety—the equivalent of police commissioner—in 1924. While running for mayor in 1923, Freeland Kendrick (1874-1953) pleaded with President Calvin Coolidge to release Butler from the Marine Corps to Philadelphia. Coolidge complied, and Butler, originally from West Chester, Pennsylvania, arrived in January 1924 with a mandate to clean up the vice-ridden city. Over the course of Butler’s first year in Philadelphia, police closed more than 2,500 speakeasies, compared to just 220 the previous year. While raids and arrests increased during Butler’s tenure, liquor law violators saw few repercussions. In 1925, of the 10,000 individuals arrested on the charge of conducting a speakeasy, only a few hundred were punished with more than a light fine.

Despite—and perhaps because of—Butler’s tenacity in pursuing Prohibition violators, he immediately clashed with Kendrick and the Republican political machine, including South Philadelphia ward boss William Vare (1867-1934). Butler left his post as director of public safety in December 1925. Many observed that his honesty and zealous commitment to enforcing Prohibition contributed to his speedy exit from Philadelphia. Upon his departure, Butler called Philadelphia the “cesspool” of Pennsylvania, and implored Quaker City citizens to demand honesty from their politicians.

A Crime Crescendo in 1928

Gangland murders, as well as Philadelphians’ continued disregard for liquor laws, reached a breaking point in the summer of 1928. Judge Edwin O. Lewis (1879-1974) charged the Special August Grand Jury with investigating organized bootlegging syndicates, gang violence, and police corruption. Investigators and journalists attributed twenty deaths in the year preceding the inquiry to bootlegging gangs vying for territory. Once again, the federal government intervened to help Philadelphia with its Prohibition-fueled crime problem. Prohibition officials in Washington ordered a unit of the Internal Revenue Service’s intelligence department to Philadelphia to aid the investigation.

[caption id="attachment_16462" align="alignright" width="300"]Members of the Special August Grand Jury The Special August Grand Jury of 1928 was jump-started by two murders involving a speakeasy operator and another member of "the trade." (Special Collections Research Center, Temple University Libraries)[/caption]

The grand jury revealed that hundreds of police officers received bribes for protecting bootlegging operations and illegal taverns. Twenty-four high-ranking police officers, each paid $1,500 to $2,500 in an annual salary, had accumulated $750,000 in assets amongst them. The grand jury’s final report found 138 police officers unfit for service, but failed to garner any indictments against the city’s organized bootlegging outfits.

Prohibition—like the prominent 1928 investigation initiated to curtail bootlegging, payoffs, and violence—proved a failure in Philadelphia, costly in financial and political terms, but also in human lives. One Philadelphia coroner noted that every day ten to twelve deaths from poison liquor, including denatured industrial alcohol improperly distilled, came to his attention. Still more deaths, including untold unreported or unsolved murders, resulted from the violence that sprang up between warring bootleg factions.

A Widespread Disregard of Prohibition

Philadelphians, like many Americans, disregarded Prohibition en masse. Despite the federal mandate, residents of the Quaker City continued to consume alcohol (legal), thereby spurring its production, transportation, and sale (all illegal). In the working class saloons of Brewerytown and Kensington, and the ritzy hotels dotting Center City’s Broad Street, Philadelphians of divergent classes saw alcohol as social ritual and social fabric. Many advocates for repeal argued that this widespread lawlessness undermined American values, creating a nation of hypocrites. Other critics of Prohibition observed that a multitude of organized crime networks sprung up to control bootlegging, creating a dangerous black market business. Still others exposed Prohibition’s financial failings, an argument that gained potency after the stock market crash of 1929.  Prohibition was costly to enforce, and the government lost millions—if not billions—of dollars in liquor tax revenue. Organizations such as the Association Against the Prohibition Amendment, which counted several members of the wealthy Delaware Valley du Pont family as its leaders, worked to defeat Prohibition. With the passage of the Twenty-First Amendment in 1933, the Eighteenth Amendment mandating Prohibition was repealed.

Liquor laws in Pennsylvania—as well as a slew of South Jersey towns—harken back to an earlier era when temperance advocates held public office. Pennsylvania Governor Gifford Pinchot, a reform-minded “dry” politician, created the Pennsylvania Liquor Control Board days before Prohibition ended so that the state would retain some control over the sale and distribution of liquor. Little has changed since Pinchot’s action; Pennsylvania is one of two states (the other is Utah) in which liquor is sold only in state-run stores. Though private retailers may sell beer, the state regulates when, where, and how much. Attempts to privatize liquor sales have met with a measure of popular and political support. However, resistance from the United Food and Commercial Workers’ Union, which represents liquor store clerks, and legislative gridlock have swiftly dissolved these efforts.

Annie Anderson is the senior research and public programming specialist at Eastern State Penitentiary and the co-author, with John Binder, of Philadelphia Organized Crime in the 1920s and 1930s (Arcadia Publishing, 2014). She received her M.A. in American Studies from the University of Massachusetts-Boston.

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