Boss Tweed and Accountability for Powerful Criminals in 19th Century New York

Crime in 19th Century New York City was often executed out in the open. One of the greatest threats to day-to-day life was posed by young pickpockets who thrived in crowded, busy streets in broad daylight.[1] The public nature of the offense made it all the easier to incarcerate those who committed it.[2] Similarly, William M. “Boss” Tweed, leader of Tammany Hall, exerted his corrupt political influence via holding highly visible public office, making no effort to obscure the massive gains he and his ring were able to make as a result of their thriving power. However, because of both Tweed’s personal wealth and the focus the criminal justice system had on eliminating low-lives such as pickpockets, Tweed was sentenced to disproportionately light sentences in comparison to the gravity of the many crimes he committed. This is reflective of the difference in treatment of crimes committed by “high criminals” (criminals with great power and wealth) and “low criminals” (criminals with no power who have little choice but to commit crime to get by).

Tweed’s Rise to Power

Boss Tweed’s rise to power was made possible via the attention-shifting tactics he used to gain the trust and popular support of the city’s denizens. Tweed as the boss of Tammany Hall benefited from the “epidemic of war profiteering” plaguing the Union in the midst of the Civil War.[3] As a member of the County Substitute and Relief committee, Tweed was tasked with relieving poor draftees who could not afford the $300 commutation fee to avoid the war and replacing them with other recruits.[4] He ultimately accomplished this task via scandalous methods, including the recruitment of unqualified soldiers.[5] However, in comparison to the ignominy of corrupt contractors “charging Uncle Sam sky-high prices for everything from diseased horses to defective pistols”, the unorthodox strategy of Tweed’s committee — which ultimately paid over 100,000 recruits for Lincoln’s army — was easily forgiven.[6] This allowed Tweed to become “a hero in New York City”.[7] Now holding an established reputation in addition to his significant wealth and political power, William M. Tweed could now afford to become embroiled in scandal and employ questionable tactics to achieve his goals. In essence, he would now be able to engage in corruption right before the eyes of the people of New York City — even as the corruption of “low criminals” that plagued the streets was harshly punished.[8]

Tweed’s “Rough Methods”

Having gained the trust of the people of New York City, Tweed could now more transparently engage in old, “rough methods” of corruption to achieve his objectives while continuing to appear generous and trustworthy through gestures such as frequent charitable donations.[9] By the end of the Civil War, Tweed was a millionaire and had established a ring of profiteers with vested interest in his continued acquisition of power, to the point where New York police would, as a rule, refuse to assist in any investigation of Tweed’s wrongdoing.[10] Beyond purchasing individuals’ loyalty, Tweed was able to buy the verdict of the court of public opinion through frequent and sizable monetary contributions to various causes, from Civil War veterans to dinners attended by a large group of people.[11] This was one of the chief methods that Tweed was able to take advantage of to avoid arrest, that the “street-rats and gutter-snipes” would have no way to access.[12] In fact, because these monetary contributions benefited the poor, Tweed secured their loyalty in the process, thus being able to use them as pawns for his benefit — leading them to continue to be incarcerated while he and other privileged criminals remained free.[13] Thus, rather than attempting to disguise his ill-gotten wealth, Tweed embraced it and took advantage of it, securing the support of New York City in the process.

An Open Secret

The money that “Tweed and his fellow corruptionists stole” became “an open secret in political circles”, and the money that the Tweed Ring funneled to New York newspapers “in the guise of advertising” resulted in silence from journalists who were also aware of what was going on.[14] By the time that Boss Tweed’s corruption became blatantly prominent, many of those with the power to fight or expose him were already deeply invested in some aspect of his web of influence. At a time when street criminals were being sentenced to years in prison for what amounted to petty theft, Tweed and his cronies were stealing millions from taxpayers without consequence thanks to the bribery of the elite, and the manipulation of the masses.[15]


The success that Boss Tweed and the Tweed Ring enjoyed in their rise to power was ultimately unsustainable, but the punishment that Boss Tweed in particular received was disproportionate to his crimes, thanks to the wealth and connections that imprisoned him in the first place. During the Gilded Age, there were a number of financial bubbles waiting to collapse, but the Tweed Ring wasn’t one of them; rather, it was a political bubble, relying on an unstable network of lies, bribery and corruption.[16] It took chaotic rioting to shift the tide of public opinion and therefore render the Tweed Ring vulnerable to exposure by the media and arrest by the authorities.[17] Tweed was eventually convicted on fifty-one of fifty-four items.[18] He was then ordered to serve 12 years “on Blackwell’s Island, a place no less notorious than the state prison at Sing Sing”.[19] Yet, ultimately, he “did not pay the $12,750 fine, nor serve the twelve years”, and only spent a single year on Blackwell’s Island.[20] The eventual civil suit brought against him, the exacerbation of his punishment after his attempt at escape, and his death in prison served as forms of justice for Tweed.[21] However, the sheer amount of wrongdoing Tweed had to commit to receive a punishment comparable to that which pickpockets and other “low criminals” experienced is indicative of the significant gap of accountability between the rich and powerful criminals and the desperate, impoverished ones in 19th century New York City.

[1] Timothy J. Gilfoyle, “Street-Rats and Gutter-Snipes: Child Pickpockets and Street Culture in New York City, 1850-1900,” in Journal of Social History, 853.

[2] Gilfoyle, “Street-Rats and Gutter-Snipes,” 870.

[3] Kenneth D. Ackerman. Boss Tweed: The Rise and Fall of the Corrupt Pol Who Conceived the Soul of Modern New York. (New York: Carroll and Graf Publishers, 2005),

[4] Ackerman, Boss Tweed, 26.

[5] Ackerman, Boss Tweed, 29.

[6] Ibid.

[7] Ibid.

[8] Timothy J. Gilfoyle, “Introduction”, in The Urban Underworld in Late Nineteenth-Century New York, ed. Timothy J. Gilfoyle (Boston: Bedford/St. Martin’s 2013), 13.

[9] Denis Tilden Lynch, “Boss” Tweed: The Story of a Grim Generation, (Ann Arbor, MI: University of Michigan Library, 2005), 284.

[10] Lynch, “Boss” Tweed, 276.

[11] Lynch, “Boss” Tweed, 277.

[12] Gilfoyle, “Street-Rats and Gutter-Snipes”, 853.

[13] Anbinder, Tyler. Five Points: The 19th-century New York City Neighborhood That Invented Tap Dance, Stole Elections, and Became the World’s Most Notorious Slum. (New York: Free Press, 2001), 331.

[14] Lynch, “Boss” Tweed, 301.

[15] Gilfoyle, “Street-Rats and Gutter-Snipes,” 870.

[16] J.D. Broxmeyer. “The Boss’s ‘Brains’: Political Capital, Democratic Commerce and the New York Tweed Ring, 1868-1871” in Journal of Social History. 383.

[17] Ackerman, Boss Tweed, 276.

[18] Ackerman, Boss Tweed, 275.

[19] Ackerman, Boss Tweed, 277.

[20] Lynch, “Boss” Tweed, 396.

[21] Lynch, “Boss” Tweed, 399; Ackerman, Boss Tweed, 344.