In this episode of History for Cocktail Parties, James Ottley and Thornton Kennedy fire up one of the most daring and cinematic episodes of the Civil War: the Great Locomotive Chase. With Chattanooga’s rugged geography as the backdrop, the hosts break down why this region became a strategic prize and how Union operative James J. Andrews hatched a plan bold enough to change the war’s trajectory. Ottley and Kennedy explore Andrews’ first failed sabotage attempt, the high-stakes mission to sever Confederate supply lines, and General Mitchell’s sweeping vision for a coordinated strike. From runaway locomotives to relentless Confederate pursuit, the episode reveals how planning, execution, and pure luck shaped one of the war’s most dramatic moments — and why one of Andrews’ raiders became the first-ever recipient of the Medal of Honor.