The Story of H.H. Holmes | Chicago’s Most Infamous Serial Killer

Posted: 12.12.2024 | Updated: 12.18.2024

When you think of the darker side of Chicago’s history, a few things come to mind: gangsters, prohibition, bank robberies, and the Great Fire. Yet, there was one man whose crimes were perhaps more heinous than any other individual who called Chicago home: H.H. Holmes. 

To learn more about the seedy underbelly of 20th-century Chicago and see some of the most haunted sites yourself, reserve a ghost tour with Windy City Ghosts tonight.  

Who Was H.H. Holmes?

H.H. Holmes is known as America’s first serial killer. During his lifetime, he’s believed to have murdered at least 27 people, while some experts believe he may have killed upwards of 200 people. 

Holmes became infamous for his twisted, tortuous ways of killing his victims in his labyrinth of a home, which has since been named the “murder castle.” 

The beginnings of H.H. Holmes’ murderous mindset

H.H. Holmes (birth name Herman Webster Mudgett) was born in 1861 to an upper-class family in New Hampshire. The boy showed high intelligence at a young age and a fascination with all things medical. This led him to perform surgeries on animals- which, today, we know can be a warning sign of serial killing tendencies. 

Excelling academically, Holmes went to medical school at the University of Michigan, where his fascination with human bodies only grew. He’d steal bodies from the morgue or even dig them up from graves and then sell them as cadavers to other medical schools.

After graduating, despite having a wife and son, Holmes left everything behind and moved to Chicago — changing his name to Dr. Henry H. Holmes in honor of the literary detective. 

The origin of the Murder Castle 

After arriving in Chicago, Holmes began working at a pharmacy. Soon after, the pharmacy owner mysteriously died. Holmes then convinced his widow to sell Holmes the pharmacy rather than run it herself. 

After the deal went through, the woman was never seen again, and Holmes told anyone who asked that she had “moved to California.”

With the income of the pharmacy behind him, Holmes purchased a large lot across the street and began building a massive, three-story residence. 

But this was no ordinary home. Holmes claimed he was building a hotel, with the top floor being reserved for his private living quarters. For the 100-room hotel, Holmes hired and fired several construction firms so no one person could connect the dots of what he was actually building: a murder castle. 

The rooms were soundproof, with several having gas lines connected to the rooms so he could easily (and silently) kill anyone he wanted to. 

Holmes also designed the building to allow him to dispose of his victims easily. Some rooms had trap doors or chutes that led directly to the basement, where Holmes had set up his own autopsy room, which included a dissecting table where he would remove the flesh of his victims and then sell the skeletons to medical schools. There was also a kiln to burn any remains. 

Holmes’ victims

Holmes began luring victims into his trap once his hotel was completed. It seemed that Holmes’ motives were often tied to making a buck, so he’d target wealthy people to stay at his hotel. 

There seemed to be a subset of victims Holmes would home in on: single women. Holmes reportedly seduced many women, even becoming engaged to several and marrying at least two. However, his fiancees seemed to have a knack for disappearing shortly after the engagement, when Holmes could collect their life insurance policy. 

One of Holmes’ employees said his charm and charisma helped him win over these women. “Holmes used to tell me he had a lawyer paid to keep him out of trouble, but it always seemed to me that it was the courteous, audacious rascality of the fellow that pulled him through… He was the only man in the United States that could do what he did.”

However, Holmes discovered an entirely new group of marks in 1893, when the biggest event in the world came to Chicago. 

The Chicago World’s Fair 

From May to October 1893, over 27 million people from all around the globe descended on Chicago to attend the great World’s Fair. Several groundbreaking inventions — like electricity and the Ferris wheel — were showcased at the fair for the first time on a large scale. 

All these excited visitors also needed places to stay, which Holmes immediately took advantage of. As these guests were from faraway places and had no family nearby, it was pretty easy for Holmes to make them disappear without raising any red flags. 

Holmes’ other fraud schemes

After the success of the World’s Fair, Chicago’s economy experienced a bit of a slump. Unwillingly to deal with that reality, Holmes headed on the road to swindle more unexpecting victims. 

His escapades included stealing horses in Texas and then selling them for a hefty profit in St. Louis. However, many of his scams centered around insurance fraud. This would ultimately be his downfall. 

The role of the Pitezel family

On his travels, Holmes met Benjamin Pitezel. Pitezel agreed to fake his own death to collect a 10,000 life insurance claim. 

Pitezel and Holmes committed this fraud in several states, and Holmes began trying to bring more people into the scheme. This included Marion Hedgepeth, another criminal. However, before Hedgepeth could get her payout, something happened between Holmes and Pitezel. 

Like so many people in Holmes’ life, Pitezel inexplicably disappeared. Pitezel’s wife had also been in on the con, and she became worried that Holmes had killed her husband for real. 

Concerned that Pitezel’s wife was going to talk, Holmes kidnapped three of her children. Around this time, Hedgepeth — feeling swindled— spoke to police about Holmes’ insurance fraud, not realizing he was also a mass murderer. 

During their investigation, police were able to tie Holmes to Pitezal’s murder. They also later found the bodies of two of the Pitezel children, theorizing that Holmes had killed them by locking them in a small trunk and pumping it full of gas. The other child’s burned body was found at one of Holmes’ cottages. 

Holmes’ conviction

Holmes was arrested in November 1894. During the interrogation process, Holmes admitted to killing 27 people, though he often changed his story.  

In 1895, Holmes was found guilty of Benjamin Pitezel’s murder and was hanged on May 7, 1896, at the age of 34.

In a final stroke of irony, Holmes requested to be buried in a cement-filled pine coffin 10 feet below ground because he was “worried about grave robbers.” 

Haunted Chicago 

H.H. Holmes is one of many wicked people who have called Chicago home throughout the centuries — some of whom still roam the streets today.

The souls killed by mobsters continue to haunt the Biograph Theater, while victims of the Order of the Golden Dawn cult are still present in the Golden Dagger gathering space. Brave enough to check out these spooky sites for yourself? Book a ghost tour with Windy City Ghosts to see if you spy anything out of the usual. 

To discover more haunted sites around the U.S., follow us on Facebook, Instagram, and TikTok. Follow our blog to stay up-to-date on the latest Chicago haunts.

Sources: 

https://www.smithsonianmag.com/smart-news/enduring-mystery-hh-holmes-americas-first-serial-killer-180977646

https://www.healthline.com/health/macdonald-triad

H.H. Holmes

https://www.biography.com/crime/hh-holmes

H. H. Holmes