1823–1878

Born and bred in New York, the jovial 300–pound William M. Tweed was perhaps the most corrupt politician that the city has ever produced. He worked his way up through the political ranks until he was Grand Sachem of Tammany Hall (a Democratic society that ran the city), and with the other members of the “Tweed Ring,” he accrued an incredible fortune through kickbacks, bribes, fraud, and theft of city funds. He and his associates were so smooth that no one is even sure how much they stole from taxpayers before they were caught in 1871; it’s estimated to be somewhere between $30 million and $200 million (or between $400 million and $3 billion today).