H.H. Holmes [serial killer

Calvin

Welcome to the infamous edition of the Headstones and Microphones where we use AI to step into the past through a researched, first-person simulation done through creative story telling of history's most infamous people. Now, let’s meet our guest.

Calvin

"Welcome to the podcast. Let’s start at the absolute beginning, where the public narrative hasn’t yet distorted who you were. When and where were you born, and what was your given name?"

White Male Guest

"Hi Calvin. I was born as Herman Webster Mudgett on May 16, 1861, in the small, isolated town of Gilmanton, New Hampshire."

Calvin

"What was your hometown and home life like as a child?"

White Male Guest

"Growing up in Gilmanton, my home life was incredibly strict and difficult. My parents, Levi and Theodate Mudgett, were devout Methodists who demanded absolute obedience. My mother was quite cold and distant, using her rigid religious views to guide her parenting, while my father was an alcoholic and an abusive, harsh disciplinarian. He would physically abuse my siblings and me for the smallest things. If he thought we were being too noisy, he would routinely try to silence us by holding rags soaked in kerosene vapor over our mouths. Because of that terror at home, I often spent my time finding refuge alone in the nearby forests."

Calvin

"Was there a story behind your name, or a nickname that stuck with you?"

White Male Guest

"As a boy, I went by Herman, but when I moved to Chicago in 1886 to start fresh, I took on the moniker Dr. Henry Howard Holmes, or H.H. Holmes. I initially chose it partly as a tribute to Sherlock Holmes, but it was also a tactical choice to keep the law and creditors from connecting me to my previous financial frauds and abandonment of my first family back East. Of course, the newspapers later gave me far more sinister nicknames, like the Beast of Chicago and the Torture Doctor."

Calvin

"What were you like as a child, and how many years of schooling did you actually attend?"

White Male Guest

"I was a highly intelligent but exceptionally quiet child, a true loner. Because of my high marks and my slightly odd, detached behavior, I was bullied and tortured by my schoolmates quite a bit. Despite the social isolation, my academic record was stellar. I graduated high school at just sixteen years old. After that, I attended the University of Vermont for a year before transferring to the University of Michigan Medical School in 1882, where I spent two years completing my medical degree and graduated in 1884."

Calvin

"Was there a specific moment when you realized you were fundamentally different from everyone else?"

White Male Guest

"There was a defining moment when I was about six years old that changed everything. A group of older schoolmates found out I was terrified of the local doctor's office, so they dragged me inside and forced me to stand face-to-face with a fully assembled human skeleton. They meant to scare me out of my wits, but instead of fleeing in terror, I found myself completely fascinated by it. That sudden, profound curiosity about human anatomy is what ultimately drove me to become a doctor."

Calvin

"What’s a decision that changed everything for you, but felt small at the time?"

White Male Guest

"During my time at medical school in Michigan, I realized just how easily human anatomy could be turned into cash. I began a habit of stealing cadavers from the university labs or body-snatching from local graves. I would take out life insurance policies on fictional people or associates, disfigure the stolen corpses to make them look unrecognizable, and then plant them to claim that the insured person had died in an accident. It felt like a clever, small-scale financial game at the time, but it set the foundation for a lifetime of fraud and violence."

Calvin

"Let's talk about your early run-ins with the law. Before the world knew your name for your most infamous actions, what was your very first arrest or interaction with law enforcement, and what were the consequences?"

White Male Guest

"Before the murders made headlines, my very first major arrest happened in July of 1894 in St. Louis. I was picked up and put in jail for fraud and selling mortgaged property. I didn't stay behind bars long, as my companion Georgiana Yoke managed to help bail me out, but that brief stint in jail proved to be my undoing. While locked up, I foolishly bragged about an elaborate ten-thousand-dollar insurance scam to my cellmate, a train robber named Marion Hedgepeth. I promised him five hundred dollars if he recommended a good lawyer for the scheme, but once I got out, I never paid him. Angered by my betrayal, Hedgepeth went straight to the authorities and blew the whistle on me."

Calvin

"At what moment did you realize your name would never be forgotten?"

White Male Guest

"It was in the autumn of 1894, when the Pinkerton detectives and the police finally caught up with me in Boston. The moment they connected me to the disappearance of my business partner, Benjamin Pitezel, and his children, the media took notice. William Randolph Hearst’s newspapers latched onto the story, launching an absolute national media frenzy. Seeing my face printed across the front pages of every major newspaper in America made it clear that the name H.H. Holmes was permanently etched into history."

Calvin

"Did fame make you more dangerous, or did it simply expose who you already were?"

White Male Guest

"The media attention didn't make me more dangerous; it simply stripped away the carefully crafted, charming facade of 'Dr. Holmes' that I had used to manipulate people for years. I had always been a con artist, a polygamist, and a fraudster operating in the shadows. The sudden spotlight didn't change my nature; it just exposed the cold, calculating survival instincts I had relied on since my youth."

Calvin

"Who do you believe betrayed you first: a person, society, or your own instincts?"

White Male Guest

"Without a doubt, it was a person: Marion Hedgepeth. If I had simply paid him the five hundred dollars I promised him in that St. Louis jail cell, he never would have turned state's evidence. My own greed and arrogance got the best of me, leading me to cheat a fellow criminal who held the key to my undoing."

Calvin

"What was your most unique habit or a random fact about you that would surprise people?"

White Male Guest

"People are often surprised to learn that during my childhood, long before I ever handled a human body, I used to wander into the woods of New Hampshire and perform amateur surgeries and dissections on small animals and stray carcasses. It was my private way of exploring the mechanics of life and death away from my father's wrath."

Calvin

"What did the public never understand about the pressure you were under at the time?"

White Male Guest

"The public never understood the sheer, exhausting complexity of maintaining my lifestyle. I wasn't just managing a pharmacy and a large building in Chicago; I was simultaneously juggling three or four bigamous marriages, dodging an army of furious creditors, and constantly weaving an intricate web of insurance frauds across multiple states just to keep my finances afloat."

Calvin

"Did you have any known rivalries that defined your career?"

White Male Guest

"My defining adversary was Detective Frank Geyer of Philadelphia. After my arrest, he was the relentless lawman tasked with retracing my steps across the country. His stubborn determination led him all the way to Toronto and Indianapolis, where he meticulously uncovered the tragic evidence of the Pitezel children, completely destroying any chance I had of claiming innocence."

Calvin

"What personal battles were you fighting privately while the world was watching?"

White Male Guest

"Privately, I was fighting a battle against my own mounting financial desperation. When the Chicago World’s Fair ended in 1893, the city hit a sharp economic recession. My cash flow dried up, my schemes started failing, and I was forced to flee Chicago and constantly travel from city to city just to stay one step ahead of the law and the insurance adjusters."

Calvin

"What was your darkest moment, and was there ever a time you wanted to walk away from it all?"

White Male Guest

"My darkest moment came when the walls were completely closing in during late 1894. I knew the police were tracking me for horse theft in Texas and insurance fraud, but I never wanted to walk away from my schemes. Instead, my instinct was to double down, running further and weaving even more desperate lies to protect myself."

Calvin

"What truth was hardest to escape when you were alone at night?"

White Male Guest

"The hardest truth to face was that my brilliant intellect had ultimately failed me. I had prided myself on being steps ahead of everyone around me, yet I was sitting in a prison cell because of a petty grudge over a five-hundred-dollar unpaid debt to a jailhouse informant."

Calvin

"When the law finally closed in, how exactly were you brought to justice? Walk me through the final arrest, the charges that ultimately stuck, and the legal outcome of your trials."

White Male Guest

"The law finally caught up with me on November 17, 1894, when I was arrested in Boston. Initially, they held me for an outstanding warrant regarding horse theft in Texas, but the investigation quickly escalated. I was officially charged with the first-degree murder of my associate, Benjamin Pitezel, in Philadelphia. During my trial in 1895, I chose to exercise my constitutional right to represent myself, completely waiving court-appointed counsel. I aggressively cross-examined witnesses and demanded scientific analysis of the evidence, but I made critical errors and eventually had to ask my lawyers to step back in. The jury took very little time to find me guilty, and I was sentenced to death."

Calvin

"What’s the craziest rumor ever told about you, and what part of your story has been exaggerated the most?"

White Male Guest

"The yellow journalism of the Hearst newspapers completely invented the myth of my 'Murder Castle.' They printed wild stories claiming my building had custom-built gas chambers, trap doors to drop random tourists into acid vats, and secret execution rooms. The mundane truth is that the building's bizarre, labyrinthine layout existed solely because I constantly hired and fired different contractors so I could avoid paying them for their labor. There were no hidden torture chambers or assembly-line killings of hundreds of World's Fair visitors."

Calvin

"What is the biggest misconception people have about your life?"

White Male Guest

"The biggest misconception is the body count. The tabloids claimed I killed upwards of two hundred people, and in a desperate bid for a financial payout from the newspapers while in prison, I even confessed to twenty-seven murders. However, many of the people I 'confessed' to killing were actually found to be verifiably alive and well. Historically, only about nine of those victims are actually confirmed."

Calvin

"What would surprise people most about your ordinary, human side?"

White Male Guest

"People see me as a completely detached monster, but I lived a remarkably ordinary domestic life at times. I was a family man who fathered children, including my son Robert and daughter Lucy. To my neighbors, wives, and business associates, I was just a charming, polite, and remarkably well-mannered country doctor."

Calvin

"When, where, and how did you pass away?"

White Male Guest

"I met my end on May 7, 1896, at Moyamensing Prison in Philadelphia, Pennsylvania. I was executed by hanging at the age of thirty-four. My neck didn't snap instantly; instead, it took me nearly fifteen minutes to slowly suffocate to death on the gallows before I was pronounced dead and laid to rest in Holy Cross Cemetery."

Calvin

"Was your downfall caused more by your own flaws or by the world changing around you?"

White Male Guest

"My downfall was entirely the result of my own personal flaws—specifically my arrogance and my greed. I grew far too cocky because I had evaded the law for so long. I underestimated the people around me, made sloppy mistakes, and truly believed I could outsmart the justice system right up until the noose was placed around my neck."

Calvin

"What past regrets did you carry with you to the end? If you could erase one decision from your life, would you—or was it necessary to become who you were?"

White Male Guest

"If I could erase one decision, it would be my choice to cross Benjamin Pitezel and his family. Turning on my closest accomplice is what set the bloodhounds of the law on my trail. Up until that point, I was just a highly successful con artist, but that final, dark turn is what sealed my fate."

Calvin

"What scared you more: getting caught, losing power, or being forgotten?"

White Male Guest

"Losing control and getting caught by the law was my absolute greatest fear. I spent my entire adult life meticulously controlling every environment, every alias, and every person around me. Being stripped of that control and locked in a cell where I could no longer manipulate my surroundings was terrifying."

Calvin

"When you look back now, do you see yourself as the villain, the hero, or something in between?"

White Male Guest

"I certainly don't view myself as a hero. In my final days, I openly admitted to the public that I felt as though I was turning into a monster, even claiming my features were changing to look like the devil himself. I am remembered as one of America's first notorious villains, and frankly, it is a title I earned through my own calculated choices."

Calvin

"Do you have any closing remarks about the interview or the stories you shared that you would like to share with the listeners before signing off?"

White Male Guest

"Only this: do not believe everything you read in the sensational headlines. Strip away the myths of the castle, and you will find that the real danger wasn't a building with secret traps—it was simply a man with a charming smile and a completely cold heart."

Calvin

"And that wraps up another conversation from beyond the grave. Thanks for joining us on The Headstones and Microphones Podcast. Remember—Do better with the life you have been given and choose to do good in this life. Please help spread the word by sharing and following the pod."