William M. "Boss" Tweed

Quick Summary

William Magear Tweed, known as "Boss" Tweed, ran the most powerful political machine in nineteenth-century America. As head of Tammany Hall, he presided over a ring that systematically looted New York City of an estimated $30 million to $200 million through fraudulent contracts, inflated invoices, and pervasive bribery between roughly 1865 and 1871. Exposed by The New York Times and the cartoons of Thomas Nast, Tweed was convicted of 204 charges in 1873, imprisoned, escaped to Spain, was recaptured, and died in the Ludlow Street Jail in April 1878.

Timeline of Events

The Details

Tweed's corruption machine operated through a deceptively simple mechanism. Any company wishing to do business with New York City was required to inflate its invoices, typically by 50% to 85%, and kick back the excess to the Ring. The scheme was administered by four key figures: Tweed himself, City Chamberlain Peter "Brains" Sweeny, Comptroller Richard "Slippery Dick" Connolly, and Mayor A. Oakey "the Elegant" Hall.

The most infamous example was the New York County Courthouse, begun in 1861 and still unfinished when the ring collapsed. A plasterer named Andrew Garvey billed the city $2.87 million for plasterwork; earning the nickname "the Prince of Plasterers." Carpenter George Miller billed $360,751 for one month of work. A furniture dealer named James Ingersoll charged over $5.6 million for furnishings, much of which never arrived. The thermometer bill alone came to $7,500.

The Ring controlled virtually every aspect of city government. Tweed sat on the boards of the Erie Railroad, the Brooklyn Bridge Company, and the Third Avenue Railway Company. He hand-picked judges, controlled the Board of Elections, and distributed patronage to an estimated 12,000 city workers who owed their jobs to Tammany. Naturalization of immigrants was fast-tracked before elections, up to 1,000 new citizens processed in a single day, in exchange for votes.

Thomas Nast's biting cartoons in Harper's Weekly, beginning in 1869, were instrumental in turning public opinion. Tweed reportedly said: "Stop them damned pictures. I don't care so much what the papers say about me. My constituents can't read. But, damn it, they can see pictures." The New York Times, under editor Louis Jennings, published the Ring's secret financial records in July 1871 after refusing a $5 million bribe to suppress them.

The exposure of the Ring was accelerated by disgruntled insiders. James O'Brien, a former sheriff denied a claim by Connolly, obtained copies of the city's financial books from county bookkeeper Matthew O'Rourke. These documents were provided to the Times, which published them as "The Secret Accounts," providing irrefutable documentary evidence of the fraud.

What Happened

Tweed was arrested on October 27, 1871. His first trial in January 1873 ended in a hung jury, widely suspected of bribery. His second trial resulted in conviction on 204 of 220 counts on November 19, 1873. He was sentenced to 12 years in prison and fined $12,750. The sentence was reduced on appeal, and he served about one year at the Blackwell's Island Penitentiary.

Upon release, he was immediately re-arrested on civil charges by the state seeking to recover $6 million. Held in the more permissive Ludlow Street Jail, Tweed was allowed visits home under guard. On December 4, 1875, he escaped during one such visit and made his way through New Jersey to Florida, then by ship to Cuba and Spain.

Spanish authorities captured him in Vigo in September 1876, reportedly recognizing him from Nast's cartoons. He was returned to the Ludlow Street Jail, where he spent his final years. Tweed attempted to cooperate with prosecutors, providing a detailed confession of the Ring's operations, but the promised leniency never materialized. He died of pneumonia on April 12, 1878, at age 55.

Of his co-conspirators, Connolly fled to Europe with several million dollars and died in exile. Sweeny also fled abroad but eventually returned and made a financial settlement with the city. Mayor Hall was tried twice but acquitted both times. None of Tweed's associates served significant prison time.

Financial Impact

Historians differ significantly on the total amount stolen. The most commonly cited figure comes from an 1877 report by the city's Board of Aldermen, which estimated losses at approximately $30 million. However, later analyses, including Kenneth Ackerman's 2005 biography, suggest the true figure may have been much higher when indirect costs, inflated property taxes, deferred infrastructure, and lost economic development, are included.

The courthouse alone cost more than the entire Alaska Purchase ($7.2 million in 1867) or the construction of the Houses of Parliament in London.

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