A man named Amsterdam (DiCaprio) seeks to avenge the death of his father at the hands of Bill "The Butcher" Poole (Day-Lewis). Set in New York City during the period just before the Civil War, Amsterdam gets caught in the middle of the equally powerful and corrupt politician machines of Manhattan.

Story of the manners and morals of New York society in the later 1800's, focusing on a handsome young lawyer who cannot decide between passion and propriety in his women.

Readings of excerpts from and critical analysis of Wharton's The age of innocence, a novel about the upper classes of New York and the story of Newland Archer's love for Countess Olenska.