The Downfall of New York’s Boss Tweed

William "Boss" Tweed, New York City, 1870
William “Boss” Tweed, New York City, 1870

William Tweed, aka “Boss Tweed,” was a ruthless 19th-century New York City politician.  He is known for his powerful influence within the NY Democratic political machine (Tammany Hall), and well as for flaunting his over-the-top corruption, fraud, and greed for over two decades.

After the Civil War, more than a million people crowded into New York City’s unpaved, manure-filled streets; many in dilapidated slums. Poverty, disease, pollution, and crime were rampant for the poor Irish and German immigrants who made up half the population. The city government offered very few basic services. Boss Tweed discovered how to provide these services and line his pockets at the same time. He personified government corruption in The Gilded Age.

William Magear Tweed was born on the Lower East Side of Manhattan in 1823, the son of a Quaker furniture maker. Young William left school at eleven to apprentice with his father. Bored with carpentry, he left and became a junior clerk at a New York mercantile firm, then advanced to bookkeeper at a small brush factory. At twenty-one, he married Mary Jane Skaden, the daughter of the factory’s owner.

William found brush making dull as well, but discovered an outlet for his restlessness in volunteer firefighting. By then, Tweed was a ruddy-faced, boisterous, man, six feet tall and nearly three hundred pounds.  By 1850, at 27, he was foreman of a new fire company, Americus No. 611, “Big 611,” with a Bengal tiger on its fire engine.

He ran for 7th Ward Alderman under the Democratic Party. Though he lost by a small margin, but he won his next race in 1852 by bribing a 3rd party candidate to split the Republican vote. William Tweed was learning how to manipulate New York politics. He was a fast learner and learned from the best—the New York City Common Council, better known as The Forty Thieves. He was now in his element and became a rising star. Tweed rapidly became one of the city’s leading politicians and one of the most corrupt.

In 1856, he was drawn into the Tammany Hall faction in opposition to Mayor Fernando Wood.  He was picked to be head of a new Board of Supervisors, formed to combat election fraud. He made his headquarters at Tammany Hall, located on East 14th Street. The board soon became an avenue for Tammany graft and corruption instead. Tweed willing and enthusiastically embraced it all.

Other powerful positions came to him – commissioner of schools, deputy street commissioner, New York state senator, and Finance Committee chairman. In Tammany Hall, he was now the most influential man in the organization. They selected him to head the city’s political machine, an authoritarian “BOSS” who would essentially would run the city. In 1861, his political enemy, Fernando Wood, was defeated in the mayoral race, giving the new “Tweed Ring” free reign of the city.

In 1864, he bought the New York Printing Company, which then became the official printer for the city.  “Boss Tweed” now wore a diamond in his necktie, orchestrated city elections, controlled the new mayor, and rewarded his political supporters. His primary source of funds came from the bribes and kickbacks he demanded in exchange for city contracts and favors.

In 1867, Tweed and his wife moved into a large mansion on Fifth Avenue and 44th Street and maintained a large stable of horses. Soon, Tweed owned a regal summer estate on the Connecticut shore as well. He gobbled up key real estate in Manhattan. Now a millionaire, Boss Tweed began to move in high society circles. He was now hobnobbing with the likes of wealthy banker J. P. Morgan. He threw lavish parties, and owned gold and diamonds worth tens of thousands of dollars.

By 1870, he had been named to the boards of the Harlem Gas Company, the Brooklyn Bridge Company, Third Avenue Railway Company and the Guardian Savings Bank, which controlled city monies.  The robber barons paid him off handsomely for allowing him to make lucrative deals in both their favors. Incredibly, a number of New York City’s most respected leaders were duped for years by Tweed, unaware of his criminal side.

In 1870, he manipulated the state legislature in Albany to grant New York City a new charter that gave local officials, rather than those in Albany, power over local political offices. It became known as the “Tweed Charter” because Tweed paid tens of thousands of dollars in bribes to state politicians for its passage.

Thousands of immigrants in New York were naturalized American citizens being able to vote. Tweed made sure the immigrants had jobs, a place to live, enough food and clothing, received medical care, and even coal to warm their flats during winter. He contributed millions to neighborhood churches, schools, hospitals, orphanages, and charities that cared for immigrants.  Immigrants in the city were grateful and voted in overwhelming numbers for Tammany Hall Democrats.

The most notorious example of his corruption was the construction of the New York County Courthouse (later called Tweed Courthouse). The city built it with stone and marble from a Massachusetts quarry owned by Tweed. The courthouse, expected to cost $500,000, wound up costing taxpayers $13 million, most of it winding up in Tweed’s pockets. The corruption was shocking in its breadth and boldness. His greed for wealth and power apparently knew no boundaries.

A carpenter was paid $360,751 for one month’s labor. A furniture contractor received $179,729 for 40 chairs. A plasterer, got $133,187 for two days’ work, earning him the nickname “The Prince of Plasterers.”   When a city committee investigated why it was taking so long to build, it spent $7,718  to print its report using the printing company owned by Tweed. He paid off dozens of judges for favorable rulings.

Boss Tweed publicly flaunted the rule of law. He hired people to vote multiple times and had deputies protect them while doing so. He stuffed ballot boxes with fake votes and had election inspectors who questioned him arrested. As Tweed said, “The ballots make no result; the counters make the result.”  At times, the Tweed Ring simply ignored the ballots and falsified election results.

An editorial cartoon shows Boss Tweed leaning on a voting booth. The caption reads: “ As long as I count the votes, what are you going to do about it?” By 1870, his power in New York was absolute – the ruler of all he surveyed. The ebullient Tweed shared his ill-gotten gains with his ring, the city comptroller, the county commissioners, and the mayor.  In total, the Tweed Ring brought in an estimated $200 million in corrupt money over its lifetime.

In the end, however, Boss Tweed’s greed was too great and his exploitation too shameless. By July 1871, two lower-level city officials with a grudge against the Tweed Ring, James O’Brien and Matthew O’Rouke, provided The New York Times publisher with reams of documents detailing the corruption with city projects. The newspaper published a string of damaging articles. Political cartoonist Thomas Nast launched his first volley of a series of caricatures in Harper’s Weekly—“Let Us Prey,” which depicted Tweed as a fat vulture feeding off the city.

Editorial Cartoon of Boss Tweed and his ill-gotten gains, 1871
Editorial Cartoon of Boss Tweed and his ill-gotten gains, 1871

A furious Boss Tweed offered bribes then threats to the editor of the New York Times to stop their reporting, but neither worked. The political cartoons created public outrage and a national scandal.  Even illiterate immigrants could understand the cartoons. Soon Tweed and many of his cronies were facing criminal charges. Nevertheless, due to his popularity amongst his base, he was reelected a state senator!

By December, 1871, Tweed’s luck had run out, and he was finally arrested and indicted. Others in his ring had fled abroad like rats on a sinking ship. It took two trials and two years to convict Tweed. The first trial resulted in a hung jury, but in a second trial, he was found guilty of more than 200 crimes. In 1873, he was sentenced to twelve years in prison and fined $12,750.

He managed to get his sentence reduced on appeals to just one year and paid only $250 in fines.  Democratic state chairman Samuel Jones Tilden vowed to take back New York City.  ‘No one is above the law,’ he declared. He filed an affidavit citing Tweed and his ring’s misdeeds, which became the basis of a civil suit for recovery of the city’s money. Tweed was rearrested in early 1875 in a civil action to recover $6 million of what had been stolen. Unable to secure the $3 million in bail set by the state, he was sent to jail yet again in New York City.

While in jail, Tweed’s lawyer’s were able to get him regular leave to visit his family, while guards waited at his doorstep. At one of these meals, he escaped out a rear door disguised as a servant and fled across the Hudson River to New Jersey.  Then he took a boat to Florida, from there to Cuba, and finally to Spain. Because Spain’s government wanted the U.S to end its support for Cuban rebels, it agreed to apprehend Tweed.

The warrant issued in New York for his arrest described him:

Fifty-five years of age, about five-feet eleven inches high, weight about two hundred and eighty pounds. Very portly, ruddy complexion, has rather large, coarse, prominent features and large prominent nose; rather small grey eyes, grey hair, head nearly bald on top from forehead back to crown. His beard may be removed or dyed, and he may wear a wig or be otherwise disguised.…

Another Thomas Nast cartoon, printed in Harper’s Weekly in 1876, led to his arrest in Spain and extradition back to New York City.  Unable to pay the $6 million judgment levied against him in the civil action, in which he was convicted of 204 out of 240 counts, he remained in jail. This time, he was granted no home visits as his wife had left him after he fled the U.S.

In an attempt to be pardoned, he gave detailed testimony, confessing his guilt and naming all his many cohorts and cronies.  It did not work. Samuel Tilden, now governor of New York, refused his pardon.  Boss Tweed died of pneumonia two years later in the Ludlow Street Prison on April 12, 1878. Everyone else, including his family, had long since deserted him. On his death, New York City mayor Smith Ely refused to fly the City Hall flag at half-staff.

Boss Tweed was one of the 19th century’s most reprehensible figures and has come to stand for all that is bad in American politics. His story serves as a reminder of the interplay between political ambition and narcissism. Tweed’s legacy endures as a cautionary tale of the dangers of unchecked political power by a single individual in government.  Nevertheless he helped to spawn further authoritarian political bosses over the years—again and again – on the local, state, and national scene … all the way to the present day.

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