Money Crimes with Nicole Lapin - Scammed to Death: H. H. Holmes' Insurance Fraud Scheme Pt. 1

Episode Date: October 9, 2025

In 1889, Benjamin Pitezel befriended a man named H.H. Holmes in Chicago. The two of them became partners in crime, and cooked up a plan to defraud a life insurance company by faking Benjamin's death. But Benjamin had no idea that his friend Holmes had other ideas. Scams, Money, & Murder is a Crime House Original Podcast, powered by PAVE Studios. Listen wherever you get your podcasts. For ad-free listening and early access to episodes, subscribe to Crime House+ on Apple Podcasts. Don’t miss out on all things Scams, Money, & Murder! Instagram: @Crimehouse TikTok: @Crimehouse Facebook: @crimehousestudios X: @crimehousemedia YouTube: @crimehousestudios To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

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One of life's greatest challenges is finding someone you can trust. A true partner you can put total faith in no matter what. And for Benjamin Pitzel, That person was Dr. Henry H. Holmes. Their friendship was rock-solid. Benjamin trusted Holmes in every aspect of his life, especially when it came to committing crimes together. But as the saying goes, there's no honor among thieves.

And Benjamin Pitesell learned that lesson the hard way. Because H.H. Holmes was no run-of-the-mill criminal. He was a serial killer. Keep your friends close, but your enemies closer. It's not just a saying. It's a means of survival because in the world we're entering trust is a trap and betrayal is often fatal. I'm Carter Roy, and this is scams, money, and murder. And I'm Vanessa Richardson.

Every Thursday, we'll explore the story of a money-motivated crime gone wrong, whether it's a notorious con, fraud, burglary, or even murder. From the archives of Crime House, The Show, Murder True Crime Stories, and Killer Minds, these are some of our favorite cases that have kept us lying awake at night wondering, if money didn't make the world go round, could all this have been avoided? And as always, at Crime House, we want to express our gratitude to you, our community, for making this possible. Please support us by rating, reviewing, and following, scams, money, and murder wherever you get your podcasts. Today's case is from Murder True Crime Stories, the first of two episodes on the murder of a small-time fraudster named Benjamin Pitzel, whose death led to the capture of the notorious serial killer H.H. Holmes. Today, we'll explore how Benjamin first crossed paths with H.H. Holmes. We'll learn how they partnered up and how it all eventually went terribly wrong. Next time, part two, I'll take you through the investigation into Benjamin's murder,

following detectives as they try to unravel a confounding case and come face to face with a serial killer. While other money managers are holding, Dynamic is hunting. Seeing past the horizon, investing beyond the benchmark, because your money can't grow if it doesn't move. Learn more at dynamic.ca.c.active. Sometime around 1889, Benjamin Pytzel was in Chicago, trying to make sense. ends meet. The 33-year-old worked mostly as a carpenter for hire, although he also had some sort of criminal past. That sort of moral flexibility came in handy during times of need. Benjamin was, after all, a married man with five children, and raising a big family wasn't cheap. But at this point in time,

Benjamin was trying to make an honest living. He had actually invented a new type of coal, in, and he was showing it off in an exhibition of sorts. And so the story goes, that was where he met a man who would change his life forever. A man named H.H. Holmes. But in order to understand the story of Benjamin Pitzel, we first have to understand who H.H. Holmes was. First off, H.H. Holmes was an alias. The infamous serial killer was actually born Herman Muddgett, a far less sinister and much more unassuming name. He was born in 1861 and grew up on a farm in New Hampshire.

Herman was a polite, smart kid with lots of promise. He was also a bit of a loner and the frequent target of bullying. One day when Herman was a kid, he had to go to the doctor's office. According to his later autobiography, older kids were constantly relaying stories about horrifying things hiding behind the doctor's closed doors. And sure enough, on this day, two other boys apparently forced Herman face-to-face with a human skeleton. They put the skeleton's hands on his face, trying to frighten him. It worked. At first. But then, something shifted. for Herman. He became intrigued by the bones, not scared of them. If there was a moment that sent

Herman down his eventual path, it might have been this one. From then on, the story goes, Herman no longer feared death. He was fascinated by it. Over the next few years, Herman's preoccupation with death transformed into a desire to go to medical school. And after graduating high school at the age of 16, he found a way to turn that dream into a reality. In 1878, a year after he graduated, 17-year-old Herman married a young woman named Clara Lovering. Clara came from a privileged family, and she had the means to pay for Herman's tuition. So Herman went off to the University of Vermont, with Clara footing the bill. but he didn't exactly fit in there.

Herman didn't get along with his roommate, and he was a little too interested in dissecting bodies. After one term, Herman decided to head back home. But the call of the medical field was too strong to stay away. One year later, in 1881, Herman gave it another go. This time, he went to the University of Michigan, where he studied under a professor named William Hurdman. He was what they called a demonstrator of anatomy,

which was the polite term for someone who dissected human bodies for science. Herman seemed to spend all of his time in his professor's office, helping him prepare and dissect bodies, and maybe joining his mentor on night trips to the graveyard. During the late 19th century, medical schools often resorted to working under the table with resurrectionists or grave robbers to get enough cadavers for teaching. And then Herman had an idea. He and a friend came up with a plan to defraud an insurance company. It would be simple.

All they had to do was steal a body, create a fake identity for it, take out an insurance policy, stage and accident. dental death, and then, voila, they could collect. Herman didn't actually go through with it, but even if it was just a daydream at this point, the idea had taken root in his mind, and he wouldn't be able to shake it off. Meanwhile, things were not going well with Herman's wife, Clara. She had moved to Michigan with him, and by then they had a son, Robert. But Herman was said to be violent toward his wife, and Clara finally seemed to have had enough. Right before Herman's graduation in 1884, Clara took their young son with her and fled back to her family in New Hampshire.

While we can't pretend to know Herman's mind, he didn't seem phased by his wife leaving him. They would never actually get divorced. He simply carried on with his life without her. Soon after Clara's departure, 23-year-old Herman graduated from the University of Michigan's Department of Medicine and Surgery. He was now officially a doctor. But after graduation, things started going south for Herman. Within a year or two, he cropped up in Chicago, now going by the alias, Dr. Henry H. Holmes. It's not exactly clear why he changed his name. but it may have been a way to evade the law. Before Holmes came to Chicago, he spent brief periods

in New York and Philadelphia. In both cities, he ran afoul of the law. In New York, people had noticed Holmes coming into town with a young boy, who then disappeared. When Holmes was questioned about it, he said the boy went back home. That story seemed to suffice, and there's some evidence to suggest that truly nothing nefarious went down. The young boy may have been Holmes' son, Robert. Either way, Holmes faced a mountain of overdue bills and angry debt collectors, so he soon left town. Then he ended up in Philadelphia,

where it was rumored that he got a job as a clerk at a drugstore. There were whispers that a young boy came into the store and purchased some medicine, right after taking it, he died. Of course, Holmes denied having anything to do with it, but again, he immediately left town. And that's how he moved on to Chicago in 1886. Shortly after arriving, he got another job at a drugstore, Holton's drugstore, to be specific.

Some reports refer to a Dr. Edward Holton as the proprietor of Holton's drugstore, a fellow University of Michigan alumnists who found Holmes to be an ideal, hard-working employee, and eventually sold the place to him. In reality, Dr. Elizabeth Holton owned the pharmacy. And at least according to some sources, she and Holmes were more than employer and employee. They were lovers. She promised to give the store to Holmes in exchange for getting married.

Holmes agreed, only for Elizabeth and her young daughter to mysteriously disappear soon after. As always, when the police asked Holmes about their disappearance, he said they simply moved away, and they seemed to take his word for it, or at least didn't pursue him as a suspect. Although the truth of the matter may be far less sensational, according to Adam Selzer, author of H. H. Holmes, the true history of the white city devil, Elizabeth simply sold the store to Holmes. Her daughter sadly passed away nearly a decade later, but from gastritis, not a gruesome murder. Either way, once Holmes took ownership of the store, he purchased a plot of land across the street and began construction on a two-story building. This building would eventually become what the tabloids

deemed as Chicago's murder castle. The moniker came later, but it was based on the weird design of the building in addition to homes eventual alleged crimes that took place inside.

There were trap doors and shoots, stairways that went nowhere, and doors that opened into walls, and a giant furnace in the basement, big enough to fit a person. In hindsight, these strange design choices were clear indications that something was seriously wrong with H.H. Holmes, but at the time of the construction, people simply found it odd. It also helped that Holmes never let anyone spend too much time working on his building. He wanted to keep the rest of the world in the dark about what he was up to.

For that reason, he constantly hired and fired new construction crews. Plus, Holmes didn't want to pay for the work being done. Every time he fired another crew, he claimed shoddy workmanship and refused to pay for their services. He did this with everyone from carpenters to furniture vendors. Supposedly, that is how he crossed paths with 33-year-old Benjamin Pitzel, a Chicago carpenter for hire. The details are a little murky, but Eric Larson's narrative nonfiction book, The Devil in the White City, suggests that Holmes hired Benjamin to work on his building in November 1889, about three years after Holmes settled in Chicago.

Adam Selzer's H.H. Holmes, the true history of the White City Devil, says the two also shared an office where Benjamin was selling a coal bin he had invented. The definitive truth of how they met has been lost to history, but once the two did cross paths, their lives would never be the same. Paramount Woe! Check out the big stars, big series, and blockbuster movies. Streaming on Paramount Plus. Cue the music.

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Now that's a mountain of entertainment Wehram Wealth We know even less about Benjamin Pitzel than we do about H.H. Holmes Which makes it hard to tell a completely full story about their partnership.

But here's what we do know. Benjamin was married to his wife, Carrie, and they had five children. He was a carpenter by trade, which explains why Holmes hired him, and he had some sort of criminal past, which perhaps explains why he and Holmes hit it off. Who knows how the subject was first broached, but one way or another, Benjamin learned that Holmes had a pension for insurance fraud schemes. For someone like Benjamin, it must have felt fortuitous. With a family of five, he no doubt needed all the extra money he could scrounge up.

And because of his questionable past, he probably had no problem bending the rules, or even breaking the law. The only question Benjamin had was how could he get involved? After Benjamin and Holmes became acquainted, they quickly grew close, so close, in fact, that they lived together for a time. We don't know whether the two pulled off any fraudulent schemes together during that period, but it seems plausible, if not probable. The historical archives refer to Benjamin as an associate of Holmes constantly in his orbit. it. And it sure seems like Holmes rubbed off on Benjamin. In 1892 or 93, after about three years of knowing each other, Benjamin landed himself in jail for a fraudulent scheme that appeared to be right out of Holmes' playbook. Essentially, Benjamin used bad checks to steal expensive suits. He did

it over and over again until finally the authorities caught on and arrested him. But, Benjamin wasn't too worried about the charges. He had his friend, H.H. Holmes, looking out for him. Sure enough, after a few weeks, Holmes bailed him out. Perhaps Holmes knew he too would need a friend if he ever got himself in trouble, or at least someone who owed him a favor down the line. For the time being, Holmes put aside thoughts of future schemes with Benjamin, he was too preoccupied with the possibility of a major event taking over Chicago

and the opportunities it might provide. You see, various cities across the United States had put in bids for the next World's Fair, and Chicago seemed poised to win. Sure enough, Chicago got the bid. And in May of 1893, the World's Fair came to the World's Fair. Windy City. Roughly 27 million attendees flocked to its grounds over its six-month run, some local, some tourists, every one of them taking in the fair's grandeur. So the story goes, Holmes took it upon himself to construct an addition to his own building

at the time. He wanted a third floor, so he could make it a hotel and rent out rooms to people attending the fair. At least, that's what he told investors to get their money. In reality, it's unclear whether Holmes ever intended to finish the construction project. This is an example of where the truth is hard to decipher from all the fiction. While many sources say Holmes opened up his hotel during the fair, author Adam Selzer discovered that he never actually did. What we do know is that a this time, many young women rented rooms from homes, and many of them mysteriously disappeared without a trace. Where homes went, people seemed to fall off the map, and rumors abounded. But there was no proof of anything seriously untoward, just a series of unfortunate circumstances. Another unfortunate so-called

circumstance, the summer of the fair, the third floor of Holmes building, the possibly unfinished one, caught fire. He had, of course, taken out insurance policies on the building to the tune of $60,000. That's worth just over $2 million today. The whole thing reeked of foul play. The insurance companies sure thought so. They refused to pay out and instead began investigating Holmes for fraud. As the insurance companies started looking into arson, Holmes left Chicago and headed south. And so apparently did his good friend Benjamin Pitzel, because the two of them had a plan to hit it rich in Texas.

Earlier in 1893, Holmes had hired a young woman named Minnie Williams as his personal secretary. They were also likely having an affair. Technically, Holmes was still married to his first wife, Clara, and by that point, Holmes had bigamously married his second wife, a woman named Murda Belknap, but he was constantly unfaithful to her. In fact, despite still being married to two different women, Holmes rented another apartment in Chicago with Minnie, and they acted like man and wife. Many might have had no idea about Holmes two wives, or maybe she did and she didn't care. Either way, Minnie grew incredibly close to Holmes. His interest in her, however, seemed to be more focused on her property. She had land in Fort Worth, Texas that he had his eye on. Eventually,

he somehow ended up with the deed to her land. Then Holmes ended up transferring that deed to Benjamin. After that, Minnie and her sister wrote a letter to their aunt saying that they were heading off to Europe for the summer with Holmes, who they referred to as Harry. Neither Minnie nor her sister were ever seen alive again after July 5, 1893. Once again, we're left to come to our own conclusions on their face. but if we are reading between the lines, Holmes got the property he wanted, and then he had to get rid of anyone who might want it back. By the latter part of the year, Benjamin and Holmes ended up in Fort Worth. They immediately began construction on a new hotel, situated, of course, on the property that they had taken from Minnie Williams.

They used aliases to throw anyone off their scent. Benjamin went by Benton F. Lyman, and Holmes went by O.C. Pratt. But their business expedition didn't last long. As usual, the two were engaged in a healthy amount of fraud. They took out tens of thousands of dollars in mortgages and loans on the building, but then never paid up. And that wasn't all. they were also accused of stealing horses. Benjamin and Holmes bought horses all over Texas,

paid for them with worthless deeds and promissory notes, and then resold the horses for cash. In Texas, that kind of crime was tantamount to treason. So the two turned right back around and ran out of town before they found themselves on the wrong end of the gallows. They regrouped in St. Louis, but they didn't have to go all the way back to the drawing board. Because for the better part of a year, Benjamin and Holmes had been quietly laying the groundwork for another scheme. They were planning to fake Benjamin's death in order to collect $10,000 from a life insurance company.

Holmes had been paying the premiums on Benjamin's policy for the last year. All they had to do was decide the time. was right, and they could spring into action. Unfortunately for Benjamin, when the time did come, his friend had slightly different plans. And Benjamin's death might not be so fake after all. Are you obsessed with Colts? Then, oh, goody, do we have a podcast recommendation for you? It's called Sounds Like a Cult, and it's a show about the modern-day cults we all follow.

It offers a more lighthearted twist on cults exploring fascinating topics like Disney adults, church camp, mom fluencers, and people who are obsessed with their Stanley Cups. On Sounds Like a Cult, Hosts Amanda Montel, Chelsea Charles, and Reese Oliver, that's me, cover a different fanatical fringe group from the cultural zeitgeist every week. With the help of expert guests and listener call-ins, sounds like a cult determines if this seemingly innocent group of the week is a live your life, a watcher back, or a get the f*** out level cult. The show is available on all major podcast platforms and new episodes come out every Tuesday. For more, find the show on Instagram at Sounds Like a cult pod. late 1893 or early 1894, Benjamin Peitzel and H.H. Holmes were laying the groundwork for a massive insurance fraud scheme. But while they waited for the right time to strike, they had other simpler schemes they could run. For example, Holmes had just purchased a new drug store

in St. Louis, and he'd started to stock up on goods. Of course, he promised to pay his suppliers later, but as always, that was an empty promise. Eventually, that caught up with Holmes. Suppliers started getting suspicious, and that led the authorities to come knocking. They arrested Holmes for fraud and selling those goods he hadn't paid for. Holmes didn't stay in prison for long.

His lawyer managed to arrange for a bail bondsman to put up the money, but he was there long enough to have one little conversation that would come back to haunt him. Supposedly, Holmes got a little too candid with his fellow inmate, the infamous Wild West outlaw Marion Hedgepeth, otherwise known as the handsome bandit or the debonair killer. Hedgepeth was in prison serving a 25-year sentence. Perhaps in an attempt to impress the outlaw,

Holmes told Hedgepeth all about the plan to fendor, fake Benjamin's death. Holmes was also willing to cut Hedgepeth into the deal. If Hedgepeth could set Holmes up with a trustworthy lawyer, Holmes would pay him $500 for the connection. Hedgepeth liked the sound of that, so he gave Holmes a name. Jeptha Howe, the younger brother of one of Hedgepeth's own attorneys. When Holmes got out of prison, he met with Howe, who was,

immediately on board with a life insurance scheme. He'd gladly help Holmes pull this off, for a fee, of course. With all the pieces in place, Benjamin and Holmes decided it was time to put their plan into action. They decided to run the scheme in Philadelphia, so Benjamin moved to Philly and rented an office under the alias B.F. Perry. He pretended to be an inventor, which was an important part of the persona

because he and Holmes planned on staging an explosion. They'd make it look like an honest accident that happened while Benjamin was working. Then Holmes would supply a cadaver and they would disfigure the corpse enough so it was unrecognizable. The insurance claim would go through, they'd collect the payout,

and no one would be any the wiser. On September 4, 1894, a man named Eugene Smith stopped by the office. The door was unlocked, and when Smith wandered in, he felt like something was wrong. He called out, and nobody answered. So Smith ran to get the police. When the authorities arrived, a rancid smell hit their nostrils. The inventor must have been experimenting with something god-awful. But then they saw the real cause of the smell.

It was a body, burned, disfigured, and practically unrecognizable. The authorities first thought was that this was an accidental death from an explosion. Near the body, they found a pipe, several matches, and a broken bottle that contained a flammable fluid. It was all plausible. The coroner's physician concluded the body had been dead for about three days before it was discovered. The man who discovered him, Eugene Smith, identified the body as the inventor, B.F. Perry. But there were some irregularities to the scene. For one, none of the man's neighbors had heard any sort of explosion in the past few days,

and this would have been a big one. Second, detectives found letters in the dead man's pockets that seemed to be from his wife. She was back in St. Louis, but wrote about joining the inventor in Philadelphia. But the weird thing was, all the bottom portions of the letters, where the signatures would be, were torn off, as if someone didn't want investigators to know the name of the person who had written them. So they had no way of contacting the wife. and no other leads. The coroner's jury ruled that the man had died in an explosion.

His body went unclaimed in the morgue for ten days, and then they buried him in a pauper's grave. Unless someone came along later, B. F. Perry would remain buried with no one looking for him. But then, the insurance company Fidelity Mutual Life Association in Philadelphia, received a letter. It was from St. Louis, and it claimed that B.F. Perry was actually Benjamin F. Pitzel. And wouldn't you know it, he had a life insurance policy taken out with the company.

In order to process the payout, the company needed to confirm the body's identification. But instead of Benjamin's wife, Carrie coming out to Philadelphia, H.H. Holmes and his lawyer, Jeptha Howe, went instead. However, they did bring one of Benjamin's daughters, 14-year-old Alice. Holmes told the insurance men that Benjamin had a few distinguishing marks. They included a mole on the back of the neck, a broken nose, peculiarly spaced teeth, and a twisted fingernail from being crushed by a child's rocking chair. They were very specific marks. If the body was, in fact, Benjamin, everyone should immediately be able to tell.

So they exhumed the body. Holmes identified it as Benjamin. Alice, Benjamin's daughter, concurred. After that, they moved the body to another cemetery, and the insurance company paid out the $10,000 policy to Holmes, who was apparently acting on Kerry Pytzl's behalf. At the time, it all seemed above board. Carrie even supposedly wrote a letter to Fidelity, praising them for paying the policy so promptly.

Fidelity ended up using that letter for promotional purposes to advertise their services. But once everything was done and dusted, Holmes went to Carrie and told her the truth. Benjamin was actually alive. This was all part of the plan he and Benjamin had hatched. The body back in the Philadelphia office, he planted it and pretended it was Benjamin. But really, they just managed to swindle the insurance company of $10,000,

which today would be about $360,000. Holmes paid carry $500 of the $10,000 insurance pay. out. Then he told her that Benjamin was simply hiding out. They just had to go meet him. Carrie was more than happy to follow Holmes' lead. She wanted nothing more than to reunite with her husband. But Holmes was about to lead her on a wild goose chase. And eventually, Carrie would start to wonder if Benjamin's business partner might not be telling her everything. Thanks so much for listening. I'm Carter Roy, and this is Scams, Money, and Murder.

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