Nineteenth-century New York City was ruled by a turbulent combination of money and politics. Each hand fed the other’s mouth. And the two never manifested themselves in so corrupt and notorious a fashion as in the legendary and infamous Tammany Hall. Tammany was founded in 1789 as a fraternal organization for “pure Americans.” They named themselves after Tamanend, a chief of the Lenape Native American tribe. They adopted extensive Native characteristics, referring to their meeting hall as a wigwam and to their leader a the “Grand Sachem,” sachem being the word for the chief of the Algonquins.

As the group politicized itself at the turn of the 19th century, Aaron Burr helped turn Tammany into a political machine, ultimately using it to help Thomas Jefferson win New York’s electoral votes, and thus the presidency, in 1800, when Burr was running as his Vice President. In the days before Welfare, poor populations would often be extorted for their votes: financial support in exchange for their numbers in the ballot boxes. Tammany greatly expanded its political power in just such a way in the 1830s and 40s by buying the loyalty and support of the city’s burgeoning Irish immigrant population.

But no individual from the powerful Tammany machine lives on in such infamy and derision as William M. “Boss” Tweed. His very name has become synonymous with the stereotypical political fat-cat. His corruption was total. His takings were immense. And his reputation is legendary.

William M. Tweed was born April 3rd, 1823 on Cherry Street in Manhattan’s teeming Lower East Side. He dropped out of school at age 11 to learn his father’s trade as a chair maker. In 1844, he married Mary Jane C. Skaden and lived with her and her family on Madison Street for two years. In 1848, he’d begin his rise to power in a seemingly innocuous manner: by helping to found a volunteer fire company.

Early 19th-century fire brigades in New York were competitive commercial enterprises. The FDNY wouldn’t be founded until 1865, and until then, fires were put out by volunteer groups paid according to the calls to which they responded. Often, these brigades had ties to neighborhoods, gangs, and ethnic groups, and often, buildings would burn to the ground as competing engines fought, fist-to-face, over who would get to put the fire out. On his brigade, the Americus Engine No. 6, Tweed became notorious for his large stature and ax-wielding violence in fights. This notoriety ultimately got him kicked off the engine, but it caught the attention of Democratic politicians who ran the Lower East’s Side’s 7th Ward.

The party put helped get him elected as a city Alderman in 1851, and to the US House of Representatives in 1852. In 1858, Tweed was appointed to the New York County Board of Supervisors, which was in the process of beefing itself up to resist pressure from Albany’s Republican leadership. This would be Tweed’s first taste of the spoils of corruption: he and his cronies on the Board would charge 15% fees to companies wishing to do business with the City.

Tweed continued to line his pockets and to establish his “ring” of supporters in powerful places. His friend, Judge George C. Barnard, certified Tweed as a lawyer, despite his total lack of legal training, and he opened a law practice on Duane Street near City Hall. In 1861, he was named Chairman of the Democratic General Committee and, in 1863, of Tammany’s General Committee. That same year, he was elected Grand Sachem of the group and began to go by the nickname “Boss.”

Boss Tweed used his Duane Street law firm to extort money, writing the income off as legal expenses. He then had himself appointed Deputy Street Commissioner, giving him considerable access to the city’s contractors and funds. He purchased the New York Printing Company and made it the city’s official printer. Then he purchased the city’s stationery supplier, the Manufacturing Stationers’ Company. He had both companies drastically overcharge for their goods and services, and he pocketed the profits. His power continuing to grow, he began elevating his friends to powerful positions within New York’s government. And he started investing his vast illegally-gotten riches in real estate, making him the city’s third-largest landholder for much of the 1860s.

As Tweed became wealthier, his reputation grew accordingly, and he caught the attention of an influential political cartoonist by the name of Thomas Nast at Harper’s Weekly. Nast’s bitingly critical drawings of Tweed and his ring of cohorts were the one major thorn in Tweed’s side during his rapid ascent. “Stop them damned pictures!” he is reported to have said, “I don’t care so much what the papers say about me. My constituents don’t know how to read, but they can’t help seeing them damned pictures!”

In 1868, Tweed was elected as a New York State Senator. At the time, several wealthy railroad barons, including Cornelius Vanderbilt, Jay Gould, and Big Jim Fisk, were locked in a bitter fight over the Erie Railroad, which connected New York to Chicago and was up for sale. Fisk and Gould issued fake bonds for the railroad, illegitimately inflating their stake in the company, driving its stock price down, and forcing Vanderbilt to drop out of the fight at a $7 million loss. Senator Tweed passed legislation declaring the bonds legitimate, thus absconding Fisk and Gould, who rewarded Tweed with a large block of company stock and a position as the company’s director.

In 1869, the city’s Tweed-placed mayor won election as New York’s new governor. He, along with a $600,000 bribe from Tweed to some Republican lawmakers, helped to rewrite New York City’s Charter, giving vastly more power to the city government, and calling for new citywide elections. It should come as no surprise that all 15 council seats were won by Tammany men. The Charter also put complete control of the city’s finances in the hands of the Board of Audit, which consisted of Boss Tweed and two of his hand-picked Tammany brothers.

Tweed and his friends found ways to siphon money from any and every project they touched. They bought extensive land holdings in Manhattan’s Upper East Side and Harlem, used city funds to improve the land with roads and plumbing, then sold the land at high markups, pocketing astronomical profits.

And the New York County Courthouse, which had been under construction since 1861, suddenly saw its cost suddenly multiply to more than $13 million, twice the amount paid for the entirety of the Alaska Purchase in 1867. Later investigation would show the extent of Tammany’s extortion: “A carpenter was paid $360,751 (~$4.9 million today) for one month’s labor in a building with very little woodwork … a plasterer got $133,187 (~$1.8 million today) for two days’ work.”

By 1871, Tweed was living in a mansion on 5th Avenue, was the director of the Erie Railroad, the Brooklyn Bridge Company, the Third Avenue Rail Company, and the Harlem Gas Light Company. He and his friends even established the Tenth National Bank to provide themselves a secure place to store their fortunes.

But that year would be marred by the Orange Riot of July 12. And it would signal the beginning of Tweed’s downfall.

Every year on July 12th, Irish Protestants held a parade in New York celebrating the anniversary of 1690 Battle of the Boyne, where England’s King William III (William of Orange) defeated Ireland’s King James II, bringing Ireland under British (and Protestant) rule. There had been violence at the previous year’s parade, as Catholic Irish laborers revolted against the anti-Catholic pageantry. 1871’s parade had been banned by Boss Tweed out of fear of further violence. But this was seen as kowtowing to the brutishness of a Catholic mob, and popular opinion forced Tweed to reverse course, allowing the parade to go forward, but with militia protection.

On the afternoon of July 12, 1871, almost as soon as the parade began its march down 8th Avenue from the Orange headquarters at 29th Street, the seething crowds of Catholic laborers lining the streets began throwing bottles, stones and bricks. The militiamen responded with musket fire, and the crowd responded in turn with pistol fire. The parade continued through Manhattan, gunfire and violence following it all the way. In the end, more than 60 civilians were killed, 150 wounded, and over 100 arrested. Enraged, the Catholic Irish population of New York blamed Boss Tweed and his cohorts for allowing the parade to carry on.

Much of the power which Tammany and Tweed possessed was made possible by a combination of two things: the voting power of Manhattan’s Catholic poor, and the turned blind eyes of Manhattan’s wealthy Protestants. The latter, in the aftermath of the Orange Riot’s bloody violence, began losing faith in Tweed’s abilities to control his constituents. Support fading on both sides, the Boss’s grip on the city began to slip. Insiders began passing information to the media, leading to global economic panic as European lenders and bond-holders began to doubt the city’s ability to repay its debts to them.

The city’s economic solvency in trouble, New York’s wealthy elites met at Cooper Union to discuss reshaping their government away from Tammany’s influence. They formed a committee which cut off the city’s funding, and none other than Judge George Barnard, the man who certified Tweed as a lawyer years before, forbade the city from spending money. Enraged unpaid government workers marched on city hall. Tammany Hall was losing its control.

Panicking, many of Tweed’s cohorts began resigning their posts, some even fleeing the country. Each one was replaced by representative of the anti-Tammany group from Cooper Union. The new City Comptroller had the city’s financial records closely examined. It didn’t take long to trace illegal profits from city projects directly from city contractors into Tweed’s pockets, and he was swiftly arrested.

Released on $1 million bail, and maintaining a strong, though weaker, political arm, Tweed ran for and was re-elected to the State Senate. However, the tide had turned against him: he was re-arrested, removed from the Senate seat, removed from his post as Tammany’s leader, and forced to pay $8 million bail to get out. At his trial in 1873, he was found guilty of 204 counts and sentenced to a year in prison. Once released, New York State filed a civil suit against him. Unable to come up with the $3 million bail, he was locked up in Ludlow Street Jail.

Tweed was allowed home visits while at Ludlow, and on one of these, he escaped and fled to Spain, where he hid out as a ship worker. Recognized in Spain from Thomas Nast’s Harper’s Weekly cartoons, he was handed over to the U.S. Government in November 1876, and sent back to prison.

In America, a desperate and broken Tweed agreed to provide information about the City’s corruption rings in exchange for his release from prison. He testified, but his political opponents refused to release his from jail anyway. He died of pneumonia in prison on April 12, 1878 and was buried at Green-Wood Cemetery in Brooklyn. The new Mayor refused to allow the City Hall flag to be flown at half-mast for him.

In his time, Tweed accomplished many great things for the City of New York: Broadway was widened and improved, land was secured for the Metropolitan Museum of Art, and the Upper East Side, Upper West Side, and Harlem were all improved and developed. But all happened to the benefit of Tweed and his friends. In today’s dollars, it is estimated that, all told, Boss Tweed stole somewhere between $1 billion and $8 billion dollars. His name remains the most potent symbol of government corruption this city has ever seen.