Nast used his talents in a campaign to undermine Tweed and rally good government forces to overthrow the boss. Cartoon after cartoon pictured Tweed as a thief. In addition to his caricatures of Tweed, Nast created the Tammany Tiger as a symbol for the Ring, and sometimes he used it as a more general symbol for the Democratic Party.
''It's hard not to admire the skill behind Tweed's system, though,'' Ackerman writes. ''The Tweed ring at its height was an engineering marvel, strong and solid, strategically deployed to control key power points: the courts, the legislature, the treasury and the ballot box. Its frauds had a grandeur of scale and an elegance of structure: money-laundering, profit sharing and organization.''
The city’s debts jumped about $100 million dollars in just two years from 1868 to 1870. Tweed was convicted in 1873 for his role in a corruption ring that stole at least $1 billion in today’s dollars and given a 12-year sentence.
Tweed escaped and fled to Spain where he was arrested and sent back to New York City. Tweed died in prison from pneumonia in 1878. Many, including Tweed himself, believed that despite his crooked ways he did a lot of good for the city, especially for the poor.
It has been estimated that during his reign of corruption, William Magear (“Boss”) Tweed, the “Tiger of Tammany,” and his political cronies stole $200 million (the equivalent of about $3.5 billion in today’s money) from the citizens of New York.
In an era in which all of the land for Central Park cost New York City $5 million, and the elaborate St. Patrick’s Cathedral cost $2 million to build, the Tweed Courthouse wound up costing New York’s taxpayers $12 million (equivalent to about $200 million today). More money was spent to build the Tweed Courthouse than was spent to construct the United States Capitol. In fact, the Courthouse was the costliest public building that had yet been built in the United States.
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.
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.
With absolute power over who could be nominated as a Democratic candidate and enormous influence over appointments to office, "Boss Tweed" was himself appointed a Deputy Street Commissioner, and began putting cronies on the city payroll for doing no work. With his substantial kickbacks, Tweed bought several companies which were promptly awarded city contracts. He was elected to the State Senate in 1867, and within months had charmed and cajoled his way to similar near-absolute control over the state's capitol.
William Magear Tweed worked at a brush factory, and moved into management after marrying the owner's daughter. He soon became a rising star in New York City politics of the 1850s and a key player in Tammany Hall, the behind-the-scenes group that had make-or-break power over local Democratic Party nominations. By the late 1850s Tweed and his associates controlled the group, and in 1863 he was elected Chair of Tammany Hall.