How H. H. Holmes Became America's Most Prolific Serial Killer

Although married to Clara Lovering, Holmes met a woman named Myrta in Minneapolis, whom he coaxed into coming to Chicago. They soon married, with Holmes neglecting to tell her that he was already spoken for. Two weeks later, he filed for divorce from Clara. Then he proceeded to buy a house for Myrta about 25 miles away in Wilmette, close enough to visit–but far enough to commit his nefarious crimes without interruption.

Unlike many serial killers, Holmes seemed to strategize his eventual murder spree with pinpoint efficiency. He purchased a vacant lot across the street from his drugstore, where he envisioned building a grand hotel, complete with shops, restaurants, and apartments, along with a number of sinister features, such as secret chutes and passages; an airtight, walk-in furnace; and hidden chambers in the basement. Holmes hired an assistant named Benjamin Pitezel and started construction, financed largely through fraud and credit.

Due to the plenitude of desperate laborers, he hired contractors to work on the building and refused to pay them once they completed the work. Because of this high rate of turnover, no one knew the entirety of the building’s secrets. One macabre element of construction involved a large furnace in the basement, ostensibly to manufacture glass. It wasn’t until after Holmes’s crimes were revealed that the furnace-installer recognized that the kiln was perfect for a crematorium, seeing as it produced no odor.

Related: Hotel of Horrors: The Murder Castle of Dr. H. H. Holmes 

When Jackson Park was chosen as the site of the fair, Holmes was set to become not only flush with cash, but also with a steady stream of young, female victims. His building–which came to be known as the “Murder Castle”–was mostly finished by May 1890. Using a series of aliases, Holmes bought furniture and fixtures on credit and never paid most of his creditors, confident he would avoid prosecution through his exemplary guile and charm.  

Holmes’s plan was to lure as many unwitting victims as possible into the Murder Castle between 1890 and 1893. Then after the World’s Fair, he would burn the building to the ground to collect the insurance money and destroy whatever evidence remained. To help deflect any future suspicion, Holmes even went so far as to ingratiate himself with officers of the local police precinct. 

One of the workers Holmes hired was Ned Conner, a pharmacist in Holmes’s drugstore. Holmes began paying attention to Ned’s wife Julia and sister Gertrude, and it wasn't long until Holmes instigated an affair with Gertrude. But with no marriage in the picture and the affair eventually discovered, Gertrude fled back to Iowa in shame, fell ill, and died shortly thereafter. Holmes went on to use his good looks and sly charm to seduce Ned’s wife, Julia. 

Around this time, Holmes actually sold Ned his pharmacy. Holmes was likely trying to avoid his debtors by making this sale. Creditors had begun to appear at the pharmacy demanding payment, and now that Ned was the pharmacy’s rightful owner, he inherited all of Holmes’s unpaid debts. With Julia and Holmes’s affair ongoing, her relationship with Ned had grown strained and tumultuous. Ned eventually abandoned Julia and his daughter Pearl to Holmes, moving out of town and filing for divorce as well. 

With Ned out of the picture, Holmes grew less interested in Julia and began to turn his sexual attention elsewhere. Yet when Julia surprised him with an announcement that she was pregnant, Holmes actually agreed to marry her, but with one stipulation: that she allow him to perform an abortion.

Related: American Ripper: H. H. Holmes's Great-Great-Grandson Claims Holmes Was Jack the Ripper 

On Christmas Eve, Holmes subdued Julia with chloroform under the guise of performing an abortion, and then he disposed of his newly betrothed. Holmes also murdered young Pearl. Neighbors asked pointed questions about Julia’s welfare, but Holmes put them at ease with assurances that she left suddenly, merely following her sister to Iowa. Vanishings in Chicago at the time were commonplace, and with an inept, corrupt police force, no one paid attention unless someone wealthy disappeared. Found bodies were often given to the medical college or the hospital for research and instruction, and skeletons were stripped and sold to doctors, museums, or private collectors.

Knowing this, Holmes paid a specialist to turn Julia's cadaver into a cleansed (or articulated) skeleton and then sold the skeleton to Hahneman Medical College in Chicago. Demand for such bodies was high back then, and grave robbing was commonplace. So, as usual, no one asked where the body came from.  

Around this same time, Holmes’s assistant Ben Pitezel visited Dwight, Illinois, seeking a cure for his alcoholism. There, he met young Emeline Cigrand and returned to Chicago with such an awestruck description of her that Holmes immediately sent her an invitation to come to Chicago to be his personal secretary. Beautiful 24-year-old Emeline came to Chicago and quickly found herself ensconced in Holmes’s web of seduction and deceit.  

Holmes told Emeline that he had claims to an English lordship, and her infatuation with him led her to take him at his word. Even though he was already married, Holmes asked Emeline to marry him, and she accepted. However, Emeline soon grew suspicious of Holmes’s activities, and she promptly disappeared. Friends and family asked about her, but Holmes responded with a tale that she had married someone and departed. Suspicion simmered, but nothing was ever proven–and her body was never found.

A man named Charles Chappell was the articulator of Holmes’s misbegotten skeletons. Soon after Emeline disappeared, Holmes sent Chappell a female cadaver with the upper body nearly stripped of flesh. Years later, investigators discovered a woman’s shoeless footprint imprinted in the enameled door of Holmes’s large vault. They speculated that Holmes used acid to speed the departure of oxygen from the vault, acid which Emeline stepped in before placing her feet upon the door—possibly in an effort to kick it open.

Related: 5 Chilling Facts About H. H. Holmes's Murder Castle 

But none of Holmes's crimes had yet come to light. At the time, the horizon was rosy. His businesses were booming. His wife, Myrta, and daughter, Lucy, were just far enough away in Wilmette, and the World's Fair, with its tourists ripe for the swindling, was on its way. All he needed now was a secretary. Fortune brought him Minnie Williams, who possessed talents for stenography and typewriting, as well as the perfect blend of need and weakness. Her guardian-uncle in Texas had bequeathed her a sizable estate (one-and-a-half to three million in adjusted dollars). Holmes met her in Boston some years before, and Minnie had fallen for him. He wooed her to Chicago on promises of European travel, an extravagant life, and children.

When Minnie arrived, Holmes wasted no time convincing her to transfer the deed to her Texas property to one of his aliases. He “married” Minnie quickly, although no official record of their union exists in Cook County, Illinois. Minnie’s sister Anna, however, was skeptical of Holmes, so Minnie invited her sister to Chicago to dispel her fears about her new brother-in-law.

Guests were flowing into Holmes’s World’s Fair Hotel, and the arrival of so many beautiful young female guests put Minnie into a jealous tailspin. Holmes rented a flat for her some distance from the hotel, so he could operate in peace. No one seemed to notice when guests began to disappear. A waitress, a stenographer, and a hotel guest all disappeared from Holmes’s hotel. Inside, the smells of various chemicals filled the air. Loved ones of the missing people asked questions, but Holmes’s answers were always extremely helpful and concerned.

To Holmes, people were objects to be acquired—he enjoyed the possession of his victims, the utter control. He gassed them in their rooms, or snuck in and subdued them with chloroform. He disposed of them via Chappell’s articulation skills, or in his basement furnace, or buried them in quicklime-filled pits.

In mid-June, Minnie’s sister Anna arrived for her visit. Anna was quickly entranced by Holmes and Chicago. The exotic grandeur of the World’s Fair left Anna dumbstruck with awe. Holmes gallantly invited her to stay for the summer, cementing Anna’s good opinion of her new brother-in-law.

Related: 6 Victorian True Crime Books 

Anna wrote excitedly to her aunt in Texas that Holmes was going to take the sisters on a world tour. Before departing, however, Holmes invited Anna on a tour of his hotel—alone. 

During that special tour, Holmes murdered Anna in his gas-filled vault. To cover up her disappearance, he invited Minnie with him to the hotel to meet Anna and disposed of her there as well. He gave their clothes to Ben Pitezel’s wife, Carrie, and at least one of their remains was given to Charles Chappell for scientific disposal.

At this point, Holmes began to realize that his many debts and the questions of victims’ family members were growing too intense for him to remain in Chicago. He set fire to his hotel, as planned, but the damage was minimal. Holmes filed an insurance claim anyway, but investigators suspected him of arson. They required payment in person to the beneficiary, which happened to be one of Holmes’s many aliases, so he never collected the settlement. 

Holmes’s creditors ambushed him with threats of legal action and jail. He fled the city for Texas, where he planned to stake his claim to Minnie’s land and further enrich himself. He left Chicago with his new fiancée, Georgiana Yoke, and his associate, Ben Pitezel. Before departing, however, he took out a life insurance policy on Pitezel.

In 1895, authorities compiled a list of the “missing” – hundreds of people who went to see the fair and were never heard from again. In June 1895, Detective Frank Geyer of the Philadelphia police force was assigned to find three of the missing children, the offspring of Pitezel. They had last been seen in the company of a suspect incarcerated in Moyamensing Prison, a man named Mudgett, who went by the alias H. H. Holmes.

An insurance company had engaged the Pinkerton Detective Agency to search for Holmes, suspecting him of swindling the company by faking the death of Pitezel. The Pinkertons caught up with him in Boston and had him arrested. He was then extradited to Philadelphia to await trial for insurance fraud. It soon became clear that Holmes did not fake Pitezel’s death at all, but rather killed him and made it look like an accident.

Related: The Pinkerton Agency: America's First Private Eyes 

Detective Geyer began his investigation by interviewing Holmes in prison, who claimed the children were traveling in the care of one Minnie Williams, en route to where their father was "hiding."  From a collection of letters taken from Holmes after his arrest, Geyer pieced together what actually happened: Since Pitezel’s wife, Carrie, thought they really had faked her husband’s death, Holmes convinced her to let him take three of the Pitezel children to see their father in hiding. Instead, Holmes traveled with Alice, Nellie, and Howard Pitezel, enjoying his control over them. The girls wrote many letters to their mother, none of which Holmes actually posted.

Months later, Carrie was crushed by anxiety and grief over the fate of her children. Using the girls’ letters to help his detective work, Geyer retraced Holmes’s footsteps with the Pitezel children, starting in Cincinnati. From hotels to rental houses, city to city, Geyer doggedly traced the children’s path to Indianapolis. Here, young Howard became troublesome, and it was here that Holmes disposed of him. Throughout his search, Geyer maintained hope that he might find the children alive. He simply could not fathom how anyone would kill three helpless children; he believed evil had boundaries. From Indianapolis to Chicago to Detroit, Geyer followed leads.

In Detroit, he discovered that Holmes had brought Carrie and her remaining two children and kept them housed separately just a few blocks from each other. In addition, he had a separate hotel for himself and Georgiana Yoke. It was all a game for Holmes, and he reveled in the possession of his pawns. But here in Detroit, Alice wrote in her unsent letters, “Howard is not with us now.”

As Geyer peeled away the layers of Holmes’s crimes, he gained a feel for the man’s lies and behavior, even as he was stricken by the children’s tragic plight, who, homesick and forlorn, were writing letters to their mother without knowing she was only three blocks away.

By this time, Geyer’s search had made the papers, and he became somewhat of a folk hero and celebrity. Readers nationwide followed his search for the missing children, including Holmes. Geyer’s search led him to Toronto, where a tip had come in about a man matching Holmes’s description who had rented a house and once borrowed a shovel. With an associate detective, Geyer visited the address, borrowed the same shovel from the neighbor, and excavated the house’s cellar, where he found the bodies of Alice and Nellie Pitezel.

In Philadelphia’s Moyamensing Prison, knowing that he would soon stand trial, Holmes began writing his memoir: a florid, narcissistic amalgam of slim fact and often outright fabrication. It is unknown whether he was delusional or simply a pathological liar. He even wrote a letter to Carrie, telling her that her children were alive and well with Minnie Williams in London. When Holmes was confronted with the new development regarding the discovery of the Pitezel children, he maintained his innocence. Holmes plotted to have his memoir published to sway public opinion on his behalf.

Related: 25 Books About the World’s Most Famous Serial Killers 

Geyer, meanwhile, returned to Indianapolis to continue his search for Howard Pitezel. Chicago police, prompted by Geyer’s discovery of the missing girls, entered Holmes’s castle in search of evidence and quickly turned up a wealth of it. Bones, a bloodstained dissection table, surgical tools, quicklime and acid, charred women’s shoes and tattered clothing, human hair plugging a stovepipe, more and more human remains, and the walk-in vault with a woman’s footprint etched into the door. Their searches also uncovered the remains of a child. Geyer traveled to Chicago only to discover that it was the body of a little girl, thought to be Pearl Conner, a name that meant nothing to Geyer. 

In all, Geyer and his associates investigated over 900 leads. Finally, on a last, desperate hunch, he stopped at a real estate office in Irvington, Illinois, on the chance that Holmes might have used it to rent a property. Lo and behold, he had. In the rental house, Holmes had installed a large wood stove. Inside the stove and flue, Geyer found human remains. Among other items, he also found Howard’s favorite toy, a tin man that his father had bought for his son at the Chicago World’s Fair. 

With the discovery of the final missing Pitezel child, Frank Geyer became America’s Sherlock Holmes. On August 19, 1895, Holmes’s Murder Castle burnt to the ground. Police suspected arson; an attempt to cover up the building’s remaining secrets.

On September 12, 1895, Holmes was indicted in Philadelphia for the murder of Ben Pitezel. Indianapolis police indicted him for the murder of Howard Pitezel, and Toronto police for the murders of Nellie and Alice. Holmes’s memoir–wherein he maintained his innocence–hit newsstands shortly thereafter.

Chicago was humiliated in the national media: No one could understand how the police department could fail to notice Holmes’s tremendous number of crimes. One of the most difficult revelations was that the Chicago police chief, during his previous career as an attorney, had actually represented Holmes in several commercial lawsuits. The Chicago Times-Herald said of Holmes: “He is a prodigy of wickedness, a human demon, a being so unthinkable that no novelist would dare to invent such a character. The story, too, tends to illustrate the end of a century.”

Holmes stood trial for Benjamin Pietzel’s death in late 1895. The Philadelphia district attorney called him “the most dangerous man in the world.” He was found guilty and sentenced to death. As he awaited execution, he confessed to 27 more murders, but his confession was a mixture of truth and lies. Some of the victims he named were still alive. His exact murder count will never be known, but some estimates range as high as 200. 

Holmes was hanged in May 1896. In 2017, two of Holmes's great-grandchildren successfully petitioned to have his remains exhumed, in order to finally put to rest a rumor that Holmes had somehow escaped the gallows and that someone else was buried in his place. Such was the power of Holmes's mystique–many refused to believe that the infamous 'White City Devil' had actually paid for his treacherous crimes.

More than 100 later, Holmes is still the most prominent example of a evil doctor who gave himself license to kill . But there have been many more, including Michael Swango, who was arrested in 1997 for at least four murders. In Swango's possession at the time: a notebook with quotes from books about killer doctors, including Dr. Henry Howard Holmes.

Read more about killer doctors and nurses:

The Lambeth Poisoner: London’s Deadly Doctor 

Murder in Paradise: Jamaica’s “Mad Doctor” Lewis Hutchinson 

The Perfect Psychopath: Dr. Petiot’s Heinous Crimes During World War II 

Death Shift: The Texas Infant Murders of Nurse Genene Jones 

Angel of Death: Inside the Mind of Serial Child Killer Beverley Allitt

Doctor Death: The Decades-Long Killing Spree of Harold Shipman 

Joan Robinson Hill: Was This Woman’s Mysterious Illness Actually Murder? 

Did Dr. Sam Sheppard Murder His Wife? 

Featured photo: Skyhorse Publishing