Charles 'Lucky' Luciano is running a crime empire from behind bars in 1936 when federal prosecutor Thomas Dewey puts him away for pandering. This film traces how, within a few years, Naval Intelligence is negotiating with the same mobster to protect New York's waterfront from sabotage and, later, to smooth the Allied invasion of Sicily using Mafia contacts on the ground. Interviews and archival material lay out Operation Underworld, the deal that got Luciano transferred to a more comfortable prison and eventually deported to Italy instead of executed or left to rot, and the murkier question of how much his network actually shaped the 1943 landings. The film moves between New York docks, wartime Sicily, and courtroom records, weighing the official Navy version against historians who think the mob's wartime contribution has been oversold. It's a story about a criminal syndicate turned into a tool of state power, and about how thin the line got between the American government and organized crime when there was a war to win.