“Boss” Tweed led the Tammany Hall political machine in which major U.S. city?

William M. “Boss” Tweed (1823 - 1878) was an American politician who, in the 1860s and ‘70s, along with his “Tweed Ring” cronies, systematically plundered New York City, collecting some 25-45 million USD (21.1-38.1 million EUR) from New York City taxpayers via political corruption; later estimates ranged as high as 200 million USD (169 million EUR).

Tweed essentially ran New York City's Democratic Party as leader of the corrupt Tammany Hall organization. He was elected to the U.S. House of Representatives in 1852 and the New York County Board of Supervisors in 1858. That same year he became the head of the Tammany Hall political machine.

Using his position and his vast network of cronies, Tweed got an 1870 charter passed that gave his associates control over the city treasury. Then, he systematically stole tens of millions of dollars from government coffers before finally being arrested in October of 1871.

Tweed was released on 1 million USD (846 million EUR) bail, but was re-elected to the New York State Senate in November, due to his personal popularity. Further corruption ensued and Tweed was re-arrested, forced to resign his city positions, and replaced as Tammany's leader. Afterwards, he was in and out of jail.

Tweed eventually agreed to testify about the inner workings of the “Tweed Ring” in return for his release, but after he did so, the governor of New York refused to abide by the agreement. Tweed remained in the Ludlow Street Jail until his death in 1878.