In this episode, we explore a chilling chapter of Edgar Allan Poe’s life and imagination. Long before he became a master of the macabre, Poe spent time at Fort Independence on Castle Island in Boston Harbor. There, he encountered the story of a deadly duel between two officers, Robert Massie and Gustavus Drane, and the dark legend that Drane was supposedly walled alive in a fort chamber as revenge.

We examine the historical duel, the fort itself, the local lore that surrounded it, and how these real-life elements may have inspired Poe’s famous story, The Cask of Amontillado. We also dive into the atmosphere of Boston Harbor in the early 19th century, Castle Island’s foggy walls, echoing corridors, and the chilling tales told by soldiers — all of which shaped the young Poe’s imagination and contributed to his enduring fascination with reveng ...