In 1876, Spanish officials arrested a common seaman stepping off a ship because they knew his face from a political cartoon. He was William Tweed, Boss Tweed of Tammany Hall, once the third largest landowner in New York City and the man accused of taking between 25 million and 200 million dollars from its taxpayers. This episode follows the chair maker’s son, born on the Lower East Side in 1823, from the brawling volunteer fire company called the Big Six to the top of a political machine.

Tweed’s method was to fill every choke point of city government with a loyalist: the mayor, the district attorney, judges, and the comptroller who kept the books closed. An 1870 city charter bought with bribes gave his ring direct control of the treasury, and a county courthouse ended up costing $13 million. Yet he also delivered coal and food to poor immigrants, funded Catholic schools and hospitals, and widened Broadway. The episode weighs the thief against the builder, then traces the freak accident, the leak, and the cartoons that ended it all.

• Tweed had a friendly judge certify him as an attorney with no legal training, so contractors could pay him exorbitant legal fees in place of open bribes.
• The courthouse cost almost twice what the United States paid for Alaska, and Tweed bought the marble quarry that supplied its stone.
• In January 1871 the county auditor who kept the secret books was kicked in the head by a horse during a sleigh ride. His replacement copied the ledgers and leaked them to the New York Times.
• Tweed begged associates to stop Thomas Nast’s drawings in Harper’s Weekly, saying his constituents could not read but could not help seeing the pictures.
• He escaped custody in December 1875, fled through Cuba to Spain, was hauled back, and died of pneumonia in the Ludlow Street jail in 1878 at age 55.