Ride Sally, Ride: H.H. Holmes

In this episode of Caviar & Criminals, Dana takes Anthony back to the glittering chaos of the 1893 Chicago World’s Fair — a moment in American history that promised innovation, progress, and possibility. But just a few blocks away from the White City’s shining lights, something far darker was unfolding.This is the story of charm weaponized.Of a man who could sell you a dream, a job, a marriage proposal… and then make you disappear.Dana walks Anthony through the twisted life of H.H. Holmes — the man often called America’s first serial killer — from his early days of scams and insurance fraud to the construction of his infamous “Murder Castle.” Hidden rooms. Sealed vaults. Gas lines. A hotel built not just for guests, but for control.And then there’s the question that still lingers: how much of the legend is true… and how much was manufactured by a press hungry for horror?Anthony reacts in real time as Dana unpacks the psychology, the manipulation, the financial grifts, and the cultural panic that turned Holmes into a monster of mythic proportions. Along the way, they explore the blurred line between con man and killer, spectacle and truth — and why America has always been fascinated by men who build empires on deception.Buckle up.Because this isn’t just a murder story.It’s a story about ambition without conscience. Hosted on Acast. See acast.com/privacy for more information.