Originally Posted by ADL Colin

Boss Tweed comes to mind.

From wiki:
"William M. Tweed (April 3, 1823 ? April 12, 1878), sometimes informally called Boss Tweed, was an American politician who was convicted for stealing between 40 million and 200 million dollars[1] from New York City taxpayers through political corruption. Tweed was head of Tammany Hall, the Democratic Party political machine that played a major role in the politics of 19th century New York. He died in jail."