On September 16, 1920, an explosion rocked the financial district in New York City; it was the deadliest terrorist attack in the United States up to that point, and would remain so for seventy-five years. The culprit was an Italian anarchist immigrant, and he was part of one of the greatest enemies of the United States government in the early part of the 20th century. Italians came to the United States in massive numbers. What drove some of their cohort to engage in violent acts against the state? What was it about anarchism as an ideology that made it so attractive to Italian immigrants at the time? And what would an anarchist picnic look like? The Italian immigrant anarchist experience goes far beyond that of the trial of Sacco and Vanzetti, and offers important lessons for a greater understanding of the nature of transnational political violence.