Gutting of 19th Century New York: Five Points History

New York City has a vibrant and rich history as one of American’s first big cities. With people from all over the world and from all social classes docking in New York Harbor during the mid 19th century, it was only a matter of time before New York was split into these class areas. Each area was known for something specific; the Five Points was known for the brutality and rampant criminal activity’s ability to manipulate local and national politics. By the 1850s, the Five Points was an area enthralled with organized crime rings. Each gang had its unique style and prerequisites, but all had their political authority. These gangs were the muscle behind political moves of the leaders, such as Mike Walsh and “Boss” Tweed. These and other leaders would gather at the infamous Tammany Hall for political rallies. The social and criminal atmosphere of the time only perpetuated the political problems. The Five-Point political influence even bled over into the presidential election of 1844. With the onset of the Civil War came the short lived but politically famous Civil War riots of 1863, however, what was left of these early 19th century gangs faded away.

If you were to ponder where the modern day gangster first came into prominence in America, one must consider the Five Points district of New York as being among the prime candidates for that dubious honor. Dormarunno (2001) describes the five points:

Five Points took its name from the intersection of the five streets: Little Water, Cross, Orange, Mulberry, and Anthony. One of the vilest slums in the history of America, the Five Points district was a rat infested, mud swamp. The district was full of broken down tenement housing with robbery and murder an everyday occurrence.

A place where only the strongest survived and the weak fell by the wayside. The young and more determined battled to find a way out of the poverty that engulfed the district like a shroud.

The district of Five Points had originally been a barren swamp back in the 1600’s. (Anbinder, 2002). When New York City was first built, a lake called Fresh Water Pond near Mulberry Street had an island in the middle of it. That island was used as a prison for slaves that tried to escape their master’s grip. Punishment for those slaves who unsuccessfully made a bid for freedom consisted of being taken to the Island, tied to a wagon wheel, lashed with a whip and beaten severely. (The Five Points Site, n.d.) Later they would be untied from the wheel, a rope placed around their neck and hung until dead. Although freemen began roaming the streets of the Five Points, the violence did not cease.

Around 1732, 73 acres of this swamp like marshland was acquired by Anthony Rutger. He wanted to drain the marshes and fill it in, but later decided not to go ahead with his enterprise. This area became known as the Collect. Gallo and Schnabel (2001) illustrate, “The area in 1784 saw a great beginning to an influx of impoverished immigrant families and became a squalid slum. Again, in the mid 1840’s vast migrations of immigrants from Ireland come to New York in hope of fleeing the potato famine, which killed an estimated 20% of the population.” With this increase in immigrants, the so called natives of this area began to form en masse in order to create methods of dealing with the sudden surge in population, since the living conditions were worsening by the minute.

European immigrants were flooding into Manhattan by the time the 1890’s came around. Italian and Eastern Europeans mostly all looking for work were boarding anything that would take them to a more livable destination. However, what they found was a, mostly, dilapidated Five Points district in New York City. Overcrowding meant they were largely left to the very worst of these areas, living in tenements already overcrowded without even the minimum basics like plumbing and sanitation. (The Five Points Site, n.d.) Each of the ethnic groups snatched whatever territory they could and defended it, keeping outsiders at bay by any means. The old gangs were by this time fading away, but newer ones had evolved from the fading of the old, after the Civil War.

In the early part of the nineteenth century, the masters of the Five Points were the butchers. For entertainment, they would organize bull baiting contests, and huge crowds would gather. Money was bet on how many dogs the bulls would gore. (Asbury, 1990). Dormarunno (2001) continues, “As a result of this, it was not long before saloons and dance halls sprang up in the streets close by Paradise Square.” Taking advantage of the huge crowds now thronging the area was the only means of survival for many. The impoverished from far and near clamored to the area and each eager to eek a living from stealing, conning, and mugging the ever increasing population of the surrounding area. Quickly, the only people left that had any means to support decent living conditions in the area fled for greener pastures.

The back rooms of these small shops that had emerged among the saloons and dance halls were often used as drinking dens. This is where the various gangs, which were around then, met. Most of these shops were owned by local politicians who profited from these speakeasies through undercutting the saloons by selling cheap spirits to the none too fussy gangs looking to get drunk in the backrooms while discussing business. (Czitrom, 1991). Among the very first of these greengrocer speakeasies to appear was run by Rosana Peers in 1825 and was situated on Center Street, just south of Anthony Street. Gangs using speakeasies as headquarters around that time were the Roach Guard, Dead Rabbits, Chichester’s and Plug Uglies (Asbury, 1990).

Five Points was a neighborhood that generated a unique American subculture, in which gangs were able to develop and eventually thrive, becoming incredibly powerful in the realm of politics. Czitrom (1991) explains, “The industrialization of the United States gave rise to anti-capitalist politics that contradicted the ideals of the Republic of America. The gangs had republicanism ideas and similar to the unions, tried to make working conditions better.” The various gangs of New York were working-class men who served as an extension of the unions, but never merged with them. The political parties were always on the lookout for ways to increase their votes by tapping into the resources of popular organizations. Political power was held by four main groups in the Five Points: saloon keepers, grocers, policemen, and firemen. (Gallo, & Schnabel, 2001). The groups had a unique ability to influence voters.

Politicians reserved jobs in the police department for young men who had been loyal to their party in previous campaigns. In return for such a high paying and secure job, the police officer was expected to contribute a portion of his salary to the party and use his influence to assist party members who got in trouble with the law. (Asbury, 1990). Policemen served valuable services to the political party, and as a result, we’re able to quickly rise out of the ranks to both party leadership and elective office. Volunteer fire companies also served as an avenue to political prominence. A fire company was as likely to show up in full force to support a particular election as to extinguish a fire. Dormarunno (1991) clarifies, “Because intimidation was such an important weapon in Five Point politics, the bare-knuckle fighters of the sixth ward’s fire companies frequently determined the outcome of a primary or election, often by fighting with a competing fire company.”

These political actions were proposed and executed from numerous halls where the gang leaders would gather. Tammany Hall, the popular name of Manhattan’s defunct Democratic machine, was the most famous of these. The lore of Tammany Hall provides both the vicarious thrills derived from reading of brazen wrongdoing and the satisfying spectacle of thwarted justice eventually taking its course. Mike Walsh, a flamboyant Irish immigrant and leader of the Spartan Association was dominant in Five Points’ politics, eventually becoming a U.S. Representative. Walsh was famous for directing his supporters to overrun Tammany meetings. (Asbury, 1990). Walsh would fire up crowds with his cocky tirades and rants, perfecting the craft of using the mob as a powerful political tool. His use of force was perfectly in keeping with the roughhouse standards of the 1840’s. Furious over Tammany Hall’s refusal to give the Spartan Association an independent voice within the party, Walsh ran for Congress and drew enough votes away from the Tammany nominee to win. Tammany finally gave up in 1846 and nominated Walsh as a regular candidate for the state assembly. (Anbinder, 2002). The fact that an Irish immigrant gang leader could become a U.S. Representative demonstrates the control and ability for Five Points gangs to manipulate politics.

Even so, no name from these years carries with it more infamy or more excitement than that of William “Boss” Tweed, Tammany’s most famous boss. He began as a volunteer fireman and ward politician in lower Manhattan. He had already been elected chief of Tammany Hall when, in 1863, the Draft Riots plunged Manhattan into social and political turbulence. (The Five Points Site, n.d.) Through involved and astute political maneuvering, Tweed managed to have Tammany Hall designated as the main administrative apparatus of President Lincoln’s draft in the city. However, his masterstroke was the simultaneous election, in 1868, of Tammany men to the governorship of the state of New York and the mayoral seat of New York City. Here Tweed, chief of Tammany and later state senator and commissioner of public works, began in earnest his true career. (Anbinder, 2002).

Tweed was assisted by four cronies: Governor John Hoffman, City Chamberlain Peter Barr Sweeney, Comptroller Daniel Connolly and Mayor A. Oakey Hall. Together, these four put into place the elaborate financial machinery that allowed them to rob New York of more than $120 million, in today’s dollars, by 1870, with more than $20 million of that finding its way into Tweed’s own purse. (Gilfoyle, Schneider, & Diamond, 2002). Asbury (1990) continues:

In 1870, Tweed received the public approval of Peter Cooper, one of the pillars of legitimate New York society. While it is true that in 1871 a few details of the scheme leaked out in the New York Times, these revelations remained largely without effect. However, a bloody riot on Orange Day, July 12, 1871, proved to be the crack in Tweed’s career. The first real public outcry arose against Tammany in the wake of this riot, and when, ten days later, the New York Times went public with the actual figures, copied from city ledgers, that proved Tweed’s fraud beyond a shadow of a doubt, the blow that had failed to land some months earlier finally struck its mark.

By the end of the year, Tweed was a doomed man. He had been arrested and released on bail, resigned his post as the commissioner of public works, and been voted out of his post as chairman of Tammany’s general committee.

The political influence of the Five Points gangs extended beyond Tweed or New York City and into national politics. The tight presidential race of 1844 between Democratic candidate James K. Polk and Whig Henry Clay, was believed by many to be decided by the New York popular vote. Borchard (2007) describes the scene:

Gangs of fighters used intimidation and outright violence to prevent voters from casting their ballots in favor of the Whig candidate. Close to five hundred thousand votes were cast on Election Day, and New York’s vote was swung in Polk’s favor by only five thousand votes. In return for getting him elected to office, Polk offered lucrative no-show jobs, allowing devotion to gambling and politics.

For years, gangs influenced elections and disrupted primaries and other political gatherings. Not only did they get people to vote for the Democratic Party, but they also prevented Whig supporters, brought in from outside of New York, from voting by using threats and brutal violence against them. (Czitrom, 1991).

The Civil War Draft Riots of 1863 represents the culmination of gang involvement in New York City politics. Throughout the early to mid 19th century, immigrant gangs struggled to survive in a city where native New Yorker’s believed they had no right to be in the first place. This attitude of the Irish and other immigrants being toxic to America made it very difficult for the gangs to establish an identity for themselves. Just as the gangs were beginning to create some sense of control for themselves in New York through politics, the Civil War Draft forced them to abandon their success and fight for a cause for which they did not believe. The bloody Draft Riots began on the morning of July 13, 1863, and lasted for five dreadful days. (Gallo & Schnabel, 2001). Dormarunno (2001) says, “The mentality gang members had was that if the blacks were freed, job competition would become even fiercer. Their political success was being overshadowed by this rise in power that the blacks were beginning to obtain.” This led to frustration, and ultimately severe violence against the black community in Five Points. The immigrant gangs believing, that given time, the black population would gain enough political influence to take away the influence they did have.

The Five Points was not just a festering eyesore on the face of New York City. Throughout the 19th century, the Five Points was considered the most highly concentrated center for crime, poverty and violence. What made this district so unique was not just the violence displayed in future books and movies; rather, it was the vast political influence brought on by the gangs. The most famous of these gangs: The Roach Guards, Dead Rabbits, Chichester’s and Plug Uglies, all were major players in the shaping of criminal and political activity in New York. From local political gatherings at Tammany Hall, led by Mike Walsh and “Boss” Tweed, to presidential elections; the influence of the Five Points gangs on New York politics is undeniable. The connection between the gangs ability to persuade voters through violence and establish themselves as the muscle behind the brains is clear. The Five Points will remain an invaluable key to the 19th century political history of New York City.


Anbinder, T. (2002). Five Points. New York, NY: Plume Printing.

Asbury, H. (1990). The Gangs of New York: An Informal History of the Underworld. New York, NY: Paragon House.

Borchard, G. (2007). The New York Tribune and the 1844 Election: Horace Greeley, Gangs and the Wise Men of Gotham. Journalism History, 33(1), 51-60.

Czitrom, D. (1991). Underworlds and underdogs: Big Tim Sullivan and metropolitan politics in New York, 1889-1913. Journal of American History, 78(2), 536-558.

Dormarunno, R. (2001). The Five Points. Lincoln, NB: Writer’s Club Press.

Gallo, J., & Schnabel, O. (2001). Five Points & Ante-Bellum New York City. Social Science Docket, 7(2), 58-59.

Gilfoyle, T. J., Schneider, E., & Diamond, A. (2002). Gangs in the Post-World War II North American City: A Forum. Journal of Urban History, 28, 658-663.

The Five Points Site: Archaeologists and historians rediscover a famous nineteenth-century New York neighborhood. (n.d.). Web.

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