Top 10 American Serial Killers Who Predated The 20th Century

Long before Netflix documentaries and true-crime podcasts, Americans were already
swapping stories about ruthless killers over newspapers, penny dreadfuls, and saloon
gossip. Serial murder isn’t a modern invention it just has better lighting and
streaming options now.

This countdown looks at 10 American serial killers (or serial-killer-level offenders)
who operated before the year 1900. They stalked riverboats, dusty frontier roads,
cramped city streets, and even respectable parlors. Their crimes helped shape early
ideas about “monsters” in human form, pushed communities to improve law enforcement,
and left behind legends that still haunt local history.

Fair warning: we’re focusing on facts and history, not glamorizing violence. The
victims matter more than the killers, and the goal here is context, not hero worship.
Think of this as a dark guided tour through America’s 18th- and 19th-century true
crime.

10. Samuel Mason – River Pirate of the Ohio

Our list opens on the American frontier, where the Ohio and Mississippi Rivers were
the original highways and perfect hunting grounds for criminals. Samuel Mason
started life respectably enough as a militia captain during the American Revolution.
After the war, debts, lawsuits, and a hot temper pushed him out of polite society and
into a more profitable line of work: river piracy.

By the late 1790s, Mason commanded a gang based around the notorious Cave-in-Rock
bluff, ambushing flatboats and keelboats along the Ohio River. Travelers drawn in by
his seemingly friendly camp regularly disappeared, their cargo and sometimes their
lives taken by Mason’s men. Contemporary reports linked him to dozens of killings,
enough to earn a massive bounty and nationwide notoriety.

In a twist worthy of a Western, Mason’s own associates eventually murdered him and
tried to cash in on the reward by delivering his severed head to authorities. The
scheme failed, and they were hanged instead a rare early example of a violent gang
eating itself alive.

9. Patty Cannon – Queen of the “Reverse Underground Railroad”

In the early 1800s, Martha “Patty” Cannon ran one of the ugliest criminal operations
in American history along the Maryland–Delaware border. While the Underground
Railroad secretly ferried enslaved people toward freedom, Cannon and her associates
did the opposite: they kidnapped free Black men, women, and children from the North
and sold them into slavery in the Deep South.

Cannon’s gang a mix of family members and hired muscle used taverns, farmhouses,
and backwoods holding pens to corral victims before marching or shipping them south.
When bodies were later discovered buried on her property, she was indicted for
multiple murders on top of kidnapping and illegal slave trading. Some accounts
suggest she personally killed several captives and even rival slave traders.

Arrested in 1829, Cannon reportedly confessed to numerous killings but died in jail
before she could be executed, possibly by suicide. Today she’s remembered less as a
“colorful outlaw” and more as a chilling example of how human trafficking, racism,
and serial violence intersected in early American history.

8. Samuel Green – Early “Public Enemy Number One”

Samuel Green wasn’t just a burglar who occasionally turned violent he was a
roaming catastrophe. Born in New Hampshire in 1796, he spent his teens and twenties
drifting across New England and Canada, breaking into homes, robbing travelers, and
killing anyone who got in his way. Newspapers later described him as one of the
first criminals in the United States to be labeled a true “public enemy.”

Green’s crimes escalated from theft and animal cruelty to brutal attacks on
salesmen, shopkeepers, and random victims during burglaries. Even after multiple
arrests, he repeatedly escaped or talked his way out of serious punishment, only to
resume his violent spree in yet another state.

His final act came inside a Boston prison, where he murdered a fellow inmate who had
informed guards about an escape plot. That killing finally brought a death sentence.
Green was hanged in 1822 a dramatic end to a short, vicious career that showed how
porous early 19th-century law enforcement really was.

7. Edward Rulloff – The “Genius Killer”

Edward H. Rulloff was the kind of criminal who would have broken the Internet: a
brilliant self-taught scholar who also happened to be extremely dangerous. Active in
New York state from the 1840s through 1870, Rulloff juggled identities as a teacher,
doctor, lawyer, and linguist while cycling in and out of prison for fraud, theft,
and worse.

Behind the façade, prosecutors believed he murdered his wife and young daughter,
though their bodies were never definitively found. Later, during a botched store
robbery in Binghamton, he killed a clerk, finally giving authorities a solid case.
Newspapers dubbed him “The Genius Killer,” fascinated by the idea that someone
working on a grand theory of language could also be capable of cold-blooded murder.

Despite public appeals to spare his life so his “remarkable brain” could be studied,
Rulloff was hanged in 1871. His brain was indeed preserved and weighed and
reportedly ranked among the largest on record which only deepened the era’s
uneasy obsession with the link between intelligence and evil.

6. Thomas D. Carr – A Veteran with a Deadly Confession

Thomas David Carr was a Civil War veteran whose postwar life spiraled into alcohol,
violence, and finally murder. In 1869, while working near Kirkwood Township, Ohio,
the 23-year-old Carr became fixated on a 13-year-old girl named Louisa Fox. When her
family broke off the relationship for obvious reasons Carr ambushed and killed
her on her way home from work.

That crime alone would have secured his place in local infamy, but Carr wasn’t done.
While awaiting execution, he gave a long, rambling confession claiming responsibility
for up to 14 additional killings across several states, stretching back to his army
service. Historians debate how many of those murders he actually committed versus
how many were morbid bragging, but it’s clear Louisa wasn’t his only victim.

Carr was hanged in 1870 before a large public crowd typical of the era’s
grimly theatrical executions. His case helped cement the image of the “drifter
veteran” as a potential danger at a time when mental health care for former soldiers
was essentially nonexistent.

5. Lydia Sherman – The Derby Poisoner

Lydia Sherman looked like a respectable New England housewife, but behind that quiet
exterior was one of the most notorious poisoners in American history. Born in 1824
and later nicknamed “The Derby Poisoner,” she spent the 1860s and early 1870s
moving between Connecticut and Rhode Island, quietly eliminating people who stood
between her and financial security.

Using arsenic then easily purchased as rat poison Sherman poisoned three husbands
and at least eight children, some of them her own and others stepchildren in her
care. At the time, sudden “fevers” and stomach illnesses were often written off as
infections, which helped her evade suspicion until multiple deaths finally raised
eyebrows.

Once toxicology tests confirmed arsenic in several exhumed bodies, Sherman was
convicted of second-degree murder and sent to prison. She briefly escaped, was
recaptured, and died behind bars in 1878. Her case fueled public fascination with
“black widow” killers and the dangers of unregulated household poisons.

4. Jesse Pomeroy – The Boston Boy Fiend

Jesse Pomeroy’s crimes shocked 19th-century Boston not only for their cruelty but
for his age. Born in 1859, he was still a young teenager when he began luring
younger boys to remote areas, attacking them, and then returning home as if nothing
had happened. Early assaults earned him a stint in a reform school, but he was
released after just over a year.

In 1874, Pomeroy murdered a 4-year-old boy and a 10-year-old girl in separate
incidents. His capture came after investigators matched footprints at one crime
scene to his distinctive boots. At trial, the press labeled him “The Boston Boy
Fiend,” and the public struggled to square his youth with the horrifying nature of
his crimes.

Pomeroy was sentenced to death, but the governor refused to sign the warrant for a
14-year-old. Instead, his sentence was commuted to life in solitary confinement. He
spent decades behind bars, becoming a grim symbol of unanswered questions about
juvenile crime, mental illness, and punishment in the late 1800s.

3. Stephen Dee Richards – The Nebraska Fiend

Stephen Dee (or Decatur) Richards brought serial murder to the American Great Plains.
Born in 1856, he left his family in Ohio in the mid-1870s and drifted west to
Nebraska, where he worked at an asylum and later as a farm laborer. In later
confessions, Richards claimed that his time working around severely ill patients
deadened his empathy and made killing easier.

Between about 1876 and 1878, Richards admitted to killing multiple men during
robberies and eventually wiping out the Harlson family a mother and her three
children on their Nebraska homestead. The murders were brutal and largely
motivated by financial gain and convenience rather than any complex psychological
motive.

Richards quickly became known as “The Nebraska Fiend,” and his trial drew large
crowds. He was convicted and hanged in 1879. Newspapers eagerly printed his jailhouse
interviews and “full confession,” turning his case into both a cautionary tale about
frontier isolation and a morbid form of entertainment.

2. Carl Feigenbaum – The Wandering Sailor Suspected of Being Jack the Ripper

Carl Ferdinand Feigenbaum is the wild card on this list. A German merchant seaman,
he wasn’t American-born, but his confirmed crime and execution took place in New
York and later investigators have suggested he might have been far more dangerous
than the record officially shows.

In 1894, Feigenbaum was arrested for the vicious murder of his landlord, Juliana
Hoffman, in Manhattan. The killing was severe enough to draw attention on its own,
but what came later made him infamous: after his conviction and execution at Sing
Sing in 1896, his attorney claimed Feigenbaum had privately confessed to harboring an
uncontrollable urge to kill women.

That confession, along with his work as a sailor and his presence in port cities,
led some modern researchers to suggest that Feigenbaum could be a viable suspect for
the still-unsolved Jack the Ripper murders in London’s Whitechapel district. There’s
no definitive proof, but his case illustrates how easily itinerant killers could
move between countries long before modern forensic tools or international databases.

1. H. H. Holmes – America’s “Murder Castle” Mastermind

If you’ve heard of only one pre-1900 American serial killer, it’s probably H. H.
Holmes. Born Herman Webster Mudgett in 1861, Holmes reinvented himself as a charming
doctor and businessman in Chicago in the late 1880s. Behind that polished façade, he
was a career con artist who dabbled in insurance fraud, identity scams, and,
eventually, murder.

Holmes built a three-story building in Chicago that later gained the nickname
“Murder Castle.” On paper it was a hotel and office space located conveniently near
the 1893 World’s Columbian Exposition. In reality, it was a maze of strange rooms,
hidden stairways, and sealed spaces, some fitted with gas fixtures or chutes that led
directly to the basement, where bodies could be disposed of or stripped for parts.

Officially, Holmes was convicted of just one murder that of his business associate
Benjamin Pitezel and definitively linked to eight others. He once claimed to have
killed 27 people, and later writers inflated that number to the hundreds, though
those huge figures aren’t supported by solid evidence. Still, there’s no doubt he
was one of the most prolific predators of his era. Holmes was hanged in 1896, but
the legend of the Murder Castle continues to loom large in American true-crime
history.

What These Early Serial Killers Tell Us About American History

Looking back at these pre-20th-century serial killers, one thing jumps out right
away: almost none of them were caught quickly. Many crisscrossed states, changed
names, or simply blended into communities where record-keeping was sloppy and
communication between jurisdictions was slow. There were no fingerprint databases,
no DNA tests, and no national crime networks just wanted posters, word of mouth,
and overworked local sheriffs.

Their cases also highlight the social blind spots of the time. Patty Cannon could
kidnap and kill Black victims for years partly because the wider society treated
their lives as disposable. Lydia Sherman slipped through the cracks in an era when
women were rarely suspected of calculated violence and when sudden illness in the
home was often blamed on “fever” instead of poisoning. Samuel Green and Stephen Dee
Richards took full advantage of frontier distances and jurisdictional confusion.

Meanwhile, Jesse Pomeroy and Edward Rulloff reveal the period’s fascination with the
psychology of crime. Newspapers obsessed over Pomeroy’s youth and Rulloff’s
intellect, asking whether evil was born or made questions we’re still arguing
about today, just with more neuroscience and fewer gallows sermons.

Perhaps the most striking thing is how quickly these men and women were turned into
entertainment. 19th-century readers devoured lurid pamphlets, trial transcripts, and
newspaper sketches of “fiends” and “monsters,” much the way modern audiences binge
crime documentaries. The packaging has changed, but our uneasy mix of fear, curiosity,
and moral outrage hasn’t.

Experiences and Reflections on Exploring Pre-1900 Serial Killer Cases

Spending time with stories like these is a weird experience. On one hand, the
details are chilling: people boarding what they thought was a safe riverboat and
never making it home, children walking through familiar neighborhoods and vanishing,
travelers trusting a boardinghouse on the prairie that turns out to be a death trap.
On the other hand, the cases feel distant, wrapped in old-fashioned language and
yellowed newsprint. That distance can make it tempting to treat them like ghost
stories rather than real tragedies.

If you dig deeper, though, the human reality starts to come back into focus. You can
almost picture the exhausted passengers who stopped at Samuel Mason’s camp after
fighting river currents all day, or the families in Kansas who realized one by one
that relatives who stayed at the Benders’ homestead were not just late they were
gone. Letters, court transcripts, and small local notices about “missing persons”
remind you that these weren’t just names on a list; they were parents, children,
neighbors, and co-workers whose deaths reshaped entire communities.

From a modern true-crime fan’s perspective, reading about pre-1900 serial killers is
also a crash course in how far criminal investigation has come. Cases that hinged on
boot prints in the mud, a suspicious bottle of arsenic, or a hastily buried body
would today generate DNA profiles, phone records, and surveillance footage. It’s
both frustrating and fascinating to realize how many of these killers were stopped
not by careful detective work, but by accidents, confessions, or sheer luck.

There’s also a responsibility element. It’s easy to turn figures like H. H. Holmes
into almost cartoonish villains the “Murder Castle” is tailor-made for dramatic
retellings but if you’re going to immerse yourself in this history, it helps to
keep a few guiding rules in mind. Avoid romanticizing the killers. Center the
victims whenever possible. Notice the systems racism, sexism, lack of mental
health care, chaotic frontier justice that allowed these crimes to continue.

Finally, these cases can shape how we experience modern safety. Reading about the
Cannon gang’s kidnappings might make you think differently about human trafficking
today. Learning how easily Feigenbaum moved between ports without notice may change
how you see global crime networks. And realizing that families in the 1870s or 1890s
felt the same shock, grief, and anger that people feel now is oddly grounding. The
technology changes, but the emotional impact of violent loss doesn’t.

So if you’re exploring the world of pre-20th-century serial killers whether
through books, documentaries, or lists like this one it’s worth treating the topic
less like a haunted-house ride and more like a guided history tour with serious
stakes. The stories are undeniably gripping, but the lessons about justice,
inequality, and human vulnerability are what make them worth revisiting.