Tammany Hall had existed since 1789 but it gained its notoriety under Tweed, a chairmaker by trade who used his popularity as a volunteer fireman to advance himself. He became an alderman in 1851 and he built his power through the election and appointment of his friends, which became known as the "Tweed Ring," to numerous offices in New York City, and even to the state legislature and judges' seats, often through illegal means. From 1860-1870, Tweed controlled all Democratic Party nominations for the city and the state.
In April 1870, Tweed secured the passage of a city charter putting the control of the city into the hands of the mayor, the comptroller, and the commissioners of parks and public works. He then set about to plunder the city. The total amount of money stolen was never known, but was estimated at between $30 and $200 million. Over a period of two years and eight months, New York City's debts increased by $81 million, with little to show for the debt.
They generally worked by presenting excessive bills for work performed. Ostensibly the bills were paid in full, but in reality only part of the amount was paid, with Tweed retaining the remainder and dividing it between his followers in proportion to their importance. For example, the city was billed $13 million to build a courthouse, which was several times the actual cost of construction; and $3 million for city printing and stationery over a two-year period.
The end came when one of the plunderers was dissatisfied with the amount he received and gave The New York Times evidence that conclusively proved the stealing was going on. In a subsequent interview about the fraud, Tweed's only reply was, "What are you going to do about it?" However, accounts in The New York Times and political cartoons drawn by Thomas Nast and published in Harper's Weekly resulted in the election of numerous opposition candidates in 1871. Tweed is attributed with exclaiming, "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 efforts of political reformer Samuel J. Tilden resulted in Tweed's trial and conviction in 1873. He was given a 12-year prison sentence, which was reduced by a higher court and he served one year. He was then re-arrested on civil charges, sued by New York State for $6 million, and held in debtor's prison until he could post $3 million as bail. On December 4, 1875, Tweed escaped and fled to Cuba and then to Spain, where he worked as a common seaman on a Spanish ship. He was identified, purportedly recognized from one of Nast's cartoons, and was extradited to New York (he was delivered to authorities in New York City on November 23, 1876), where he died in debtor's prison two years later.