The Terrifying True Story Of America's Youngest Serial Killer

Illustration for article titled The Terrifying True Story Of America's Youngest Serial Killer

In 1872, 12-year-old Jesse Pomeroy was briefly sent to reform school after brutally attacking several children. After his release, “the Boy Fiend” progressed to murder. A new book takes a look at this unusual case, one of the first to bring the insanity defense — and all its complications — into the public eye.


We spoke with Emerson College literature professor Roseanne Montillo about her just-released The Wilderness of Ruin: A Tale of Madness, Fire, and the Hunt for America’s Youngest Serial Killer; it’s an intriguing blend of true crime and Boston history, and offers a look at the early days of psychology and the legal system.

Illustration for article titled The Terrifying True Story Of America's Youngest Serial Killer

io9: Why did you want to tell the story of Jesse Pomeroy?

Roseanne Montillo: Actually, I was working on my first book, [The Lady and Her Monsters: A Tale of Dissections, Real-Life Dr. Frankensteins, and the Creation of Mary Shelley’s Masterpiece], browsing through the Harvard University archives, and I came across a collection of materials that belonged to one of the detectives. His name was James R. Wood, and he was a very famous detective here in Boston. He joined the Boston Police Department in the 1860s, and he rose through the ranks very quickly. Eventually he opened up his own detective agency, the first one in New England. So he was very well-known, and it was odd because of all the cases among the hundreds that he’d worked, Jesse Pomeroy stood out as the one that really frightened him. It really made him think more about evil in general. So I thought it was unusual that Wood, who was such a hardcore detective, should be a little bit frightened by a 14-year-old boy. I thought, “What could be so horrible about a teenage boy that he would scare a grown man?” I figured maybe there was something there that I should look into.

Other than the obvious factor of his young age, what were some of the things about Jesse Pomeroy that made him so unusual and frightening?

Montillo: He was born in Charlestown in 1859 — not too far from Boston. Strangely enough, he was born with a little bit of a mark on his right eye. It was called “an albino eye,” and it looked like a milky substance [covering the iris]. From the very beginning, he was seen as being very different from the rest of the boys in his neighborhood. Automatically he became the butt of many jokes. He was picked on by the children, and even by his own father, who believed that the white mark was the sign of the devil. He beat him up to see if he could almost perform an exorcism on him.


Jesse suffered a lot. But he realized as time went by that pain had sort of turned into pleasure. And not only did he start to enjoy the beatings that he got, he realized he could actually make other people suffer. So from a very young age he started beating up children who were much younger and smaller than himself. He got off on the pain that he was inflicting on other children.

And then of course it became much more gruesome than that.

Montillo: He started off by killing animals in his neighborhood. People saw him running around the neighborhood with knives and dead kittens in his hands. He killed his mother’s pet birds. But eventually, people started hearing about an older boy who was befriending the little children in the neighborhood, and he was taking them into secluded areas, giving them candy, maybe telling them that the circus was in town and they should go see it. But as soon as he had them by themselves, he would tie them up, beat them, strip them, cut them with a little knife, and sexually molest them. He really got more gruesome as time went by, and it got worse and worse.


People started to realize that they had something incredibly horrible on their hands, but they didn’t know how to get a handle on him. They began to think that maybe the devil had come to town, because only an evil person could do something like this.

As the book points out, though, he didn’t exactly prove elusive to police. The first time he was caught, it was because he walked into a police station, right?


Montillo: He actually gave himself up. There was an article that came out in the Boston Globe in 1872 about the crimes that were being committed, and Jesse’s mother, who was a real character herself, kind of recognized that the description of this person that the children were giving looked like her son. She suspected him, but instead of going to the police or to a doctor or anywhere to find help, she decided to move the family from Charlestown to South Boston. But in South Boston, he did the same very same thing, assaulting little kids.

Eventually one boy was able to tell the police that the one thing that stood out for him was that the assailant had an unusual-looking eye. So they started looking for someone matching that description, but they really didn’t have to do much; one day, out of the blue, Jesse thought it would be fun to just walk into the police station, and the boy he assaulted was right there and recognized him.


Wilderness of Ruin discusses how Jesse’s second trial offered an early, high-profile showcase for the insanity defense, though Jesse’s lawyers ended up not pursuing it. Did this case have an impact on others in the future?

Montillo: Well, Jesse was one of the earliest examples of a child who kills other children. The state didn’t really know what to do with him. Up until the point that he gave himself up, he’d abused children but he hadn’t killed anybody. He was sent to reform school — it was believed that if he stayed in reform school for six or seven years, until he was 18, he would get better, and that this was just a momentary lapse. Growing pains, if you will. But he didn’t stay there that long, and he got out about a year later. As soon as he did that, he went back to his old habits, and they got worse: he killed two children.


So the question was, you had him in your custody. Why did you let him go? And now that he’s killed, and been caught again, what do you do with him now? Do you hang a boy of 14? Put him in jail or in a mental institution? Lots of people wanted him to be studied. They thought that maybe it would be a good way to learn about children who kill other children. But many people in Boston thought he should just die. There shouldn’t even be a trial, they should just do away with him.

For the most part, though, his lawyers tried to mount some kind of an insanity defense, that he’d just had a mental lapse. But it didn’t really work, because they could trace every single step that he’d taken. Most of the crimes that he committed were completely premeditated. He’d brought knives, ropes, and he’d looked into the children. He knew very well what he was doing. So, what do you do now? The insanity defense wasn’t going to work with him anymore.


The book contextualizes the life and times of Jesse by really delving into what Boston was like at the time of his crimes. Why did you decide to frame the story that way, and how did Herman Melville and Oliver Wendell Holmes become a part of it?

Montillo: Back then, Boston was really divided by class. There were the very wealthy, and the very poor. Few people were in between. Jesse was on the poor end of things, living with his mother after his mother and father had separated. Mr. Pomeroy went his own way, and Mrs. Pomeroy got a job doing anything that she could do. She cleaned houses, she took in laundry, and she had a little shop where she sold odds and ends. But really nothing was enough. And this was a time when the wealthy didn’t care too much about what happened in the neighborhoods where the poor people lived. Crimes that were committed in areas like Charlestown and South Boston, people didn’t know too much about, and they didn’t want to know too much about. These were issues that the poor had to deal with ... until Jesse brought out the idea that, maybe you should be paying a little bit more attention to what happens outside your neighborhood. He looked everywhere, he walked everywhere. He could have taken a shine to any child that belonged to any parent. He really brought home the idea that the social divide shouldn’t exist anymore, and it was very painful for people to see that.


Herman Melville was in the area during the trial, which took place in December of 1874. He was fascinated by the case, as he was with anything that had to do with crime and mental illness. His own family had lots of people who had unfortunately gone through all kinds of mental disease: his father, his brother, his son, his niece. He was fascinated, but he was also afraid that one day he’d succumb to it as well. The Jesse Pomeroy case emphasized those issues that he was always worried about, and that he used in his fiction as well.

Oliver Wendell Holmes was in town, obviously, he was a doctor, and he studied mental illness as well. He followed the case, and when he found out that Jesse had been found guilty and was going to be executed — because initially, he was sentenced to death — Holmes believed that the best thing to do would be to place him in a mental institution and to really get to know him, to figure out why he had done the things he’d done.


Holmes thought you could learn a lot from Jesse, and he didn’t believe that Jesse was the only child who could do these things. He thought that people had a tendency to underestimate children, and that there’d be another Jesse Pomeroy out there. Most likely, there was one already. And maybe if you learned about Jesse, it would be easier to help the next boy who needed help. He saw Jesse as being very useful, so he tried hard, writing letters to the governor to make sure that Jesse would go to a good place. But nobody really listened to him; [the common mentality was] you had two choices: you killed Jesse, or you placed him in jail.

How has the system changed since Jesse’s case?

Montillo: I spoke to someone last night at a reading who said, “I work with children all the time, and today we’d see the signs early on. We’d know that a child who taunts other children, who goes around with a knife, who kills animals ... well, maybe you should pay attention to that.” Back then, no one knew what Jesse was going though. Even his mother just believed that it was part of growing up, and eventually he’d grow out of it and become a normal boy. That’s not to condone anything that she did or didn’t do, but the support system is a lot better today.


I was interested to read that some people blamed Jesse’s habit of reading lurid dime-store novels as contributing to his behavior. It’s almost like when you hear about a school shooter, and someone blames the kid’s love of video games.

Montillo: Very much so. It was an easy excuse to blame the reading material. If you go back and read the things those children had their hands on, the dime novels were not the greatest literature that you could find, but kids would save whatever money they had to buy them. The stories were full of butchery — cowboys and Indians, and detectives — I was reading some of them, and the amount of blood that was gushing out of everywhere, I was like, “Really? Children would read these things?” But they did! And there were people who thought maybe you shouldn’t give a publication like this to a 12- or 13-year-old boy, because you don’t know what kind of affect it will have on his mentality.


Jesse really loved them. He read dozens of them. His lawyers, and doctors, thought maybe the books instigated something in him, and he wanted to try them out to imitate the things he was reading, and to see if he could get away with it. Which kind of makes sense when you think of it, but it was really an easy way to blame society in general for what he did.

Which is what we still do today!

Montillo: Things haven’t really changed all that much.

What was the overall experience of writing Wilderness of Ruin like?

Montillo: It was interesting. I learned a lot — it was scary to learn about Jesse, but also to learn about what was done to him, as well. It was interesting to process his background, and how he grew into the person that he became. It’s not as simple as just saying, “He was a killer.”



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