1871 - Detail
1875 - Detail

October 27, 1871 - New York politician Boss Tweed is arrested. Thomas Nast, German-American caricaturist, who had skewed the Boss Tweed ring in his cartoons, is credited with an important role in his downfall.

December 4, 1875 - New York City politician Boss Tweed escapes from prison and migrates to Cuba, then Spain. He would be captured and returned to New York authorities on November 23, 1876.

Article by Jason Donovan

“Power tends to corrupt, and absolute power corrupts absolutely. Great men are almost always bad men.” John Emerich Edward Dalberg Acton. “Unlimited power is apt to corrupt the minds of those who possess it.” William Pitt the Elder, Earl of Chatham 1770.

From a lowly immigrant upbringing to a ruler of men, from the top to the grave, a fall has occurred. A well-dressed crime boss wrapped in the respectability of a powerful politician, the 6-foot 300-pound political kingpin, with his men in key positions, had seized and plundered the city of New York for years. The following covers the slaying of the giant of Tammany Hall and the fall of William Magear “Boss” Tweed.

Tammany Hall

Tammany Hall was the current headquarters of the Tammany organization first formed in 1789 as the Society of Tammany after a Delaware Indian chief named Tammanend. The society was originally tasked with opposing the Federalists. As the 19th century moved along, Tammany allowed Irish members to join after they forced their way into a central committee meeting in 1817. The organization was also a philanthropic society that provided food, clothes, shelter, and employment to the immigrant poor who returned the favor with their votes. Tammany would continue to accumulate power within the Democratic party. Then there was the Boss.

William Magear Tweed was born in New York City on 3 April 1823 to Scottish immigrant parents. He left school at the age of 11 so he could work with his father as a chairmaker. Later in his life, he was apprenticed to a saddler and worked as a bookkeeper. Tweed was also a rather large and imposing figure, at 6 feet tall and 300 pounds. He began his path to ruin in 1840.

Boss Tweed Runs for Office

1840 was the year he would become a volunteer firefighter. In 1850, he ran for the first public office as a city alderman. An alderman represents a district or ward within a city government. Although he would lose this first attempt, he was undeterred, and at the next election, he would win his bid, serving in this position from 1852-1853. Tweed was destined to find a home within the arms of the corrupt officials of the Democratic party structure. In the meantime, he continued his climb to the top of New York politics. 1852 Tweed was elected to the House of Representatives from 1853 to 1855. All the while, he tightened his grip on power by winning a seat on the city board of supervisors in 1856. He accomplished his continued rise to the top.

As he headed the General Committee, 1860 was an important year for Tweed. 1860 was the same year he started one of his money-making schemes by opening a phony law office as a front to conceal illicit payments for his services. Extortion was only one revenue stream for Tweed.

Tweed would solidify his power in 1868 by becoming the highest official of the Tammany organization, the Grand Sachem. He was now the kingpin of New York, both city and state. Tweed was now a crime boss with his tentacles, which he used to seize the levers of power. An example was when the tyrant installed his picks by having the mayor, governor, and state assembly speaker elected. These were only three of the Boss’s men who were elected or assigned to important positions of government. The “Tweed Ring” was a child resulting from the patronage or spoils system.

Today, this system might be called pay-to-play or outright bribery. In this system, the victors get the spoils. Loyalty and donations were rewarded by being appointed to positions in all levels of government, including cabinet positions. Due to this system, government officials were loyal to their patrons, not the public. Tweed would create an inner circle of his empire this way.

As with most, if not all, criminal groups, Tweed had an inner circle of his most trusted associates. He installed these men in crucial positions, such as Mayor A. Oakey Hall, city Comptroller Richard B. “Slippery Dick” Connolly, and city Chamberlain Peter Barr “Bismarck” Sweeny.” As with many crime bosses, Tweed used gangs around the city, such as the Irish gang The Dead Rabbits, in order to keep the populous in line. Tweed was a mob boss masquerading as a politician — an example of a cartoon villain. For, roughly, three years, the Tweed Ring bled the vibrant city of New York of any city’s government’s life, blood, money. Tweed’s organization operated much as the then-fledgling mafia would come to operate. Arguably one of the most blatant examples of the dirty tricks that the Ring employed to keep control was the mayoral victory of John T. Hoffman, as Herbert Hillary states in his book “(1888) The Tweed Ring in New York City.”

“In 1865 the Ring obtained control of the mayoralty. Its candidate, John T. Hoffman, was a man of much higher character than his supporters and associates. He was personally honest, but his ambition blinded him to acts of his political friends. His initial resistance to the operations of the Ring seems to have been overcome by the promise of the governorship.”

The promise for his loyalty came when he became governor in 1868. Hilary continues when he talks about how the election was won, “His election was secured by the grossest and most extensive frauds ever perpetrated in the city, e.g. illegal naturalization of foreigners, false registration, repeating votes, and unfair counting.” Voter fraud was not the only way the Ring defrauded New York.

There were many ways the Ring made its money. The Ring was overbilling for work that was done or billing for work that was not meant to ever be done. They also awarded no-bid contracts as long as the business paid a fee for the favor. Or worse, they created a contract with no one just to pocket the money themselves. 1870 would see a new city charter pass, and this was good news for the Ring; it increased their grip on power as they were made the “board of audit.” Like any cartoon villain, the Ring had their nemeses.

Nemeses and Tweed's Downfall

Tammany Hall had three such nemeses, the first two in the form of the newspapers of the day led by The New York Times and their support for political cartoonist Thomas Nast, whose cartoons were published in Harper’s Weekly. As was stated above, Tweed’s support came from the Irish immigrant community. Like many new immigrant communities of the time, many, if not all, of his supporters, could not read what was written, but they could get the point through the cartoons. The third party of the trifecta was an anti-corruption lawyer and reformer, Samual J. Tilden. These three would drive the wolves to the hunters.

Samual J. Tilden was not a person in the background. He made his political career fighting corruption. Between 1865 and 1875, he restructured the Democratic Party of New York, working from the inside to rip the cancer of corruption out of the political system of New York.

The trifecta would work together to turn public opinion against the Tammany and Boss Tweed. With a light shining on the Boss’s operation, the public turned on him. As the revelations came out as to the amount and the extent of the looting of the city’s treasury, $379 million to $253 million (as of 2025). Nast kept the cartoons coming, for him there was a personal angle to his fight against Tweed. Tweed and Nast grew up in the same neighborhood, as Nash had immigrated from Germany as a child. Tweed had unknowingly made a lifelong enemy after beating Nast as a child. All the attention now focused on the Ring, Tweed’s empire started to falter. Nast’s artistry was having the desired effect.

Tweed was arrested on 27 October 1871 and charged with 55 charges of embezzlement, larceny, and forgery, totaling 102 counts. Tweed and his associates had been barred from touching additional public funds via an effective injunction since 7 September. Tweed’s trial kicked off on 1 January. The prosecution was a disaster, and as a result, the trial ended in a mistrial. Tweed’s hubris was on full display when he boasted that “no jury could convict him.” The state would go for round two.

Tweed returned to court with his second trial starting on 5 November 1873. On their second try, the prosecution had all their ducks in a row, so to speak, even though there was not much evidence put forward during the trial. In the end, the jury returned a guilty verdict on 19 November 1873. Tweed was sentenced to 12 years in prison and a $12,750 fine (roughly $335,330 as of 2025). His lawyers would appeal this verdict, and the court of appeals would lower his sentence to one year. Tweed’s legal troubles were not done.

Tweed would serve his one-year sentence and be rearrested after his release as New York started a civil trial to recoup some of the money lost to his illicit activity. Tweed was remanded on a bail of $3 million (roughly $86 million in 2025). Even with all his ill-gotten gains, Tweed could not afford to post bail and was sent to Ludlow Street jail. Due to his fame and notoriety, the warden gave him special treatment. On 4 December 1875, the warden’s trust would come back to haunt him. While on his regular evening carriage ride, the Boss made his move and forgot to come back. Tweed was on the run. From New York City, he fled to Cuba and then to Spain. Spain would be where his run came to an end as a result of Nast’s artwork. While in Spain, Tweed was recognized by a police officer. He would be returned to the United States, dying in prison on 12 April 1878 in New York City.

The other two large players in this affair went on to jobs in government. Nast would have a falling out with the editors at Harper’s Weekly. This decision was detrimental to both Nast and Harper’s. Nast would have his fortune nearly wiped out when the firm handling his investments went bust, leaving him bankrupt after Harper’s Nast had trouble finding work. He would end up in Ecuador when President Theodore Roosevelt, “… appointed Nast a minor diplomat.” This assignment was in 1902. Nast would arrive in the country in 1906. He would die of yellow fever soon after arriving. Then there was Tilden.

Tilden’s post-Tweed career would go on for decades. He would run and win the 1874 election for governor of New York. Throughout his governorship, he won the public’s attention as a strong reformer. He would use this spotlight to make a run for President in 1876, a victory snatched during the Compromise of 1877 when two sets of electors came to the meeting of the Electoral College from three states. Even with losing, Tilden still had power within the Democratic party. Unlike Nast, Tilden’s investments paid off, leaving him very wealthy. Following his death on 6 August 1886, Tilden’s wealth would be used to build a library in New York.

The story of Boss Tweed follows a similar storyline to that of a comic book villain and his adversaries. Boss Tweed was the natural outcome of the spoils system. His greed blinded him to the right path. As a result of this greed he pushed his enemies into action. Nast battled Tweed with a pen, and Tilden worked to weaken Tweed from within. These battles’ effects were to bring down a political Godzilla. Nast’s legacy is that of “the father of political cartoons.” Tweed is a warning as people with ruthless motivations, endless ambition, and unending lustful greed have, in most cases, ended in the formation of a quasi-feudal system. The lesson from this episode in American history is that when you run a government like a mob boss, the crime fighters will find a way to bring one down. The citizenry will only take so much.

Photo above: William Magear "Boss" Tweed, date unknown, Hoxis Collection. Courtesy Library of Congress. Photo below: Three Thomas Nast Cartoons of Boss Tweed, various dates, Harper's Weekly. Courtesy Library of Congress. Info Source: Martin, Gary. ““Absolute Power Corrupts Absolutely” - the Meaning and Origin of This Phrase.” Phrasefinder, 2019; Zeidan, Adam. “Boss Tweed | Biography & Facts.” Encyclopædia Britannica, 2019; Britannica, The Editors of Encyclopaedia. "Tammany Hall". Encyclopedia Britannica, 2024; Moore, Tony. “Boss Tweed - Money Scam, Life & Tammany Hall.” Biography, 2019; Boss Tweed Trials: 1873, University of Massachusetts; Grigsby, Patrick Wayne. “It’s Philanthropy but It’s Politics Too”: How Tammany Hall Filled the Void after New York City’s Public Charity Failed, 1857-1905.” Tamu.edu, 2023; Lamoureux, Aimee. “The Rise and Fall of Boss Tweed’s Tammany Hall.” All That’s Interesting, All That’s Interesting, allthatsinteresting.com; Tikkanen, Amy. “Spoils System | Definition, Examples, Significance, & Facts.” Encyclopædia Britannica, 2018; Boss Tweed and Accountability for Powerful Criminals in 19th Century New York | the NYC Criminal. Fordham University; “The Tweed Ring.” U-s-History.com, 2019; “Cartoons | Boss Tweed | Political Cartoonist | Thomas Nast.” ThomasNast.com; Hillary, Herbert. “(1888) the Tweed Ring in New York City.” Scribd, 2025; “Boss Tweed Trials: 1873 - Reformers Fight Back.” Jrank.org, 2024; Samuel J. Tilden | American Politician.” Encyclopedia Britannica; “$12,750 in 1873 → 2025 | Inflation Calculator.” in2013dollars.com; Ballard, Matt. Overlooked Orleans. 2016, cobblestonemuseum.org; “Today in History - December 4.” The Library of Congress, 2015; “Thomas Nast (1840-1902).” Macculloch Hall Historical Museum; “Samuel Jones Tilden.” National Governors Association; Wei, Stella. “Thomas Nast: The Rise and Fall of the Father of Political Cartoons - Illustration History.” illustrationhistory.org, 2021.

History Photo Bomb

Old Faithful Geyser, Yellowstone National Park, circa 1872. By the Hayden Survey, William H. Jackson, Photographs. Courtesy National Archives.

Jesse James, circa 1882. Courtesy Library of Congress.

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