Tweed became a powerful figure in Tammany Hall–New York City’s Democratic political machine–in the late 1850s. By the mid 1860s, he had risen to the top position in the organization and formed the “Tweed Ring,” which openly bought votes, encouraged judicial corruption, extracted millions from city contracts, and dominated New York City politics. The Tweed Ring reached its peak of fraudulence in 1871 with the remodeling of the City Court House, a blatant embezzlement of city funds that was exposed by The New York Times. Tweed and his flunkies hoped the criticism would blow over, but thanks to the efforts of opponents such as Harper’s Weekly political cartoonist Thomas Nast, who conducted a crusade against Tweed, virtually every Tammany Hall member was swept from power in the elections of November 1871.
All the Tweed Ring were subsequently tried and sentenced to prison. Boss Tweed served time for forgery and larceny and other charges but in 1875 escaped from prison and traveled to Cuba and Spain. In 1876, he was arrested by Spanish police, who reportedly recognized him from a famous Nash cartoon depiction. After Tweed’s extradition to the United States, he was returned to prison, where he died in 1878.