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ONE OF THE most powerful politicians in New York City in the years following the Civil War, William Marcy “Boss” Tweed for a time led the formidable Tammany Hall political ring, but ultimately died behind bars a broken man. While in power, Tweed personified the political and financial corruption that often plagued American cities during the Gilded Age.

Tweed was born in New York City and, in early life, held a variety jobs including bookkeeper, chair maker, and volunteer fireman. It was through his work with the fire department that Tweed first became involved in ward politics. He parlayed his local influence into a seat as an alderman in 1852, and soon afterwards he won election as a Democrat to the U.S. House of Representatives. By 1856, Tweed was back in New York City, where he won election to the New York Board of Advisors. Tweed became a true political force after his 1863 election as “Grand Sachem” of the Society of Tammany. The group was originally a fraternal organization, but by the Civil War it had become heavily involved in New York City politics.

From his position as leader of “Tammany Hall,” Tweed held power through his ability to control patronage in the city. He made certain that corrupt friends were appointed to important offices, and held several positions himself. Following the Civil War, “Boss” Tweed and his Tammany Hall friends had a fierce grip on politics in the city, controlling not only patronage, but New York City's cash flow as well. Corruption was widespread as the group siphoned away millions of public dollars for their own use. Estimates vary widely, but the Tammany ring may have stolen as much as $100 million 1868–70.

A political cartoon of Tammany Hall Boss Tweed by illustrator Thomas Nast, 1876.

Like other political bosses of the period, Tweed led a ring that was efficient in providing city services, regardless of his personal misdeeds. His organization secured various types of relief for the poor, funding for increased construction and renovation of hospitals, public buildings, and city streets, and land for museums and parks. This made Tweed very popular with many New York voters, especially the working class, who came to view him as a larger-than-life Robin Hood figure and did not question his methods.

As Tweed lined his pockets, Thomas Nast, an influential cartoonist for Harper's Weekly, began a campaign to expose the Tammany ring. In his popular caricatures, Nast usually portrayed Tweed as a bloated, well-dressed swindler with no conscience, and at least some New Yorkers began to take notice. Tweed and his friends unsuccessfully pressured the magazine to fire Nast, and reportedly offered the cartoonist a bribe of several hundred thousand dollars to cease his activities. Eventually, Tweed's conduct drew significant public attention, and New York governor Samuel Tilden established a commission to investigate fraud and corruption in New York City. Hoping to topple the boss from power, Tweed's rivals within the Democratic Party began cooperating with the investigation, offering evidence of Tweed's crimes. In 1873, Tweed was convicted of corruption and sentenced to 12 years in prison. While the initial sentence was reduced, the state of New York sued the disgraced politician for millions of dollars and filed additional charges. In 1875, Tweed escaped from prison, fled to Cuba, and eventually made his way to Spain, where he was arrested by Spanish authorities who identified him using one of Nast's cartoons. Tweed was extradited to the United States and died in prison on April 12, 1878.

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