William Marcy Tweed, aka "Boss Tweed," began as a New York City volunteer fireman but worked his way up the political ladder. He was elected to the U.S. House of Representatives in 1853. In 1858, he rose to the head of Tammany Hall, the central organization of the Democratic Party in New York, and was later elected to the New York State Senate in 1867.
Tweed gathered around him a small ring of bigwigs who controlled New York City's finances. Tweed's Ring essentially controlled New York City until 1870, using embezzlement, bribery, and kickbacks to siphon massive chunks of New York's budget into their own pockets — anywhere from $40 million to $200 million (or $1.5 billion to $9 billion in 2009 dollars).
Companies under control of the Tweed Ring would bill the city for work not done or would overbill for work they did, and the kickbacks would filter back to Tweed and his cronies. Those companies, under city contracts, would also do substandard work that would soon require repair, which would then be done by other Tweed Ring-controlled companies. Also, because Boss Tweed had a large stake in New York's transportation system, he delayed the construction of the subway system for years.
Boss Tweed and his cronies were eventually taken down in large part because of investigative journalism by the New York Times and by the political cartoons of Thomas Nast in Harper's Weekly. Tweed was tried and convicted of forgery and larceny in 1873 and given a 12-year sentence. He was released after only one year but was soon arrested again and sued by New York City in a $6 million civil suit. In 1875, he fled to Cuba and then to Spain, but authorities were waiting for him there, and he was extradited back to New York. He died in prison in 1878.
Although the Tweed Ring is a dark mark on our history that defined government corruption for an entire century, its destruction is also a testament to the success of the free press. Had it not been for the investigative journalism of New York Times reporters and Thomas Nast's political cartoons (which could be understood even by the illiterate), Tweed's corruption wouldn't have been brought to light, and Tweed might not have been brought to justice.