Jesse Harding Pomeroy has few, if any, rivals for the title of naughtiest boy in American history. Other lads have wrecked trains, burned buildings, and done away with their friends in all sorts of cruel and imaginative ways. But Jesse makes them all look like dirty-faced angels “hooking” apples from a cranky farmer.

Jesse was not an occasional miscreant. He was no Saturday night saboteur or casual killer of playmates. Jesse’s crimes were vicious, unrepentant, and ongoing. He enjoyed every minute of ’em, freely violating the laws of God and man, all the while wearing a wickedly ecstatic grin on his face. Many bad children outgrow their violent delinquency to become upstanding citizens, or at least sensible, respectable criminals. Not Jesse. He was well on his way to becoming the next John Wayne Gacy. When they finally sent him away to prison for good at the ripe old age of 14, a mere life sentence wasn’t enough. The good people of Massachusetts were so incensed with Jesse’s crimes, they made him stand in the corner all by himself for the first 40 or so years.

It’s not hard to understand what made them so mad. Jesse was a very, very naughty boy—the Jack the Ripper of the junior high school set. He specialized in torturing, and sometimes killing, young boys between the ages of 4 and 8, using an elaborate modus operandi involving ropes, knives, pins, and sticks. He killed two children and assaulted at least seven more in a criminal career that scarcely spanned a year. At times, he was attacking a boy a week. Nor was he simply acting on some adolescent peevishness or making an unconscious, pre-New Age “cry for help”. Jesse knew exactly what he was doing and why. He loved it! Although contemporary accounts make no mention of any overtly sexual acts, every one of Jesse’s attacks was marked by strong overtones of sexual sadism. His surviving victims invariably remembered Jesse smiling, even laughing as he beat and stabbed them.

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All this, and it was only 1872. Grant was President, Victoria Queen. The Transcontinental Railroad had just been completed. Jules Verne was finishing Around the World in 80 Days. George Custer was riding strong, still several years from his encounter with Sitting Bull. Even Jack the Ripper was 14 years away from his ascension into myth. And there was Jesse, short pants, high collar and all, terrifying Boston with crimes lurid enough to keep a regiment of modern day true crime hacks busy churning out cheesy red-on-black paperbacks with titles like The Tot Torturer or The Boston Boy Killer.

Early warning signs

For all the horror of his crimes, Jesse had a surprisingly normal background. He was born in Charlestown, Massachusetts on November 29, 1859. His mother was a seamstress, his father a laborer in the nearby Boston Naval Yard. His father later quit this job to enter the butcher business. Years later, after Jesse’s arrest, Sunday supplement theorists found great significance in this career change. Mrs. Pomeroy, however, shot down this theory. Her husband’s duties primarily involved toting cattle carcasses around the market. Jesse had not spent his formative years helping Dad at the slaughterhouse. Jesse’s flair for butchery needed no such external inspiration.

Jesse had been a sickly baby. He developed a serious “humor” shortly after birth. He recovered from this apparently serious affliction (whatever it was) by the time he was seven months old, but it left him scrawny and frail. Either the humor or another infant illness scarred the cornea of his right eye, leaving a noticeable mark. But he rallied back from these early health problems. Save for the spot on his eye, he looked like any other chubby toddler, romping around the flat and playing with his older brother Charles by his third birthday.

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However, all parties (save his mother) agree that there was something noticeably strange about Jesse from an early age. He wasn’t just another nice normal little boy. It’s not that he was especially bad. That came later, in spades. Unlike many of his brethren in the multiple murderer fraternity, his younger years weren’t a confusion of habitual truancy, strangled puppies, and playground brawls. The only dark portent from his childhood is a neighbor’s possibly apocryphal story about 5-year-old Jesse stabbing a cat and tossing it into the river.

No, the odd thing about Jesse was what he wasn’t doing. He seldom played, or even spoke with the other children in the neighborhood. Even as rambunctious games of “old cat” and “kick the can” raged up and down the street, Jesse quietly remained aloof. He preferred to spend his time reading dime novels, especially those published by the Beadle and Munro publishing houses. His favorite series was based on the grisly exploits of Simon Girty, a real-life renegade white man who led the Shawnee Indians on many a frontier settler massacre in the 1780s. His subsequent activities showed undeniable touches lifted from cowboy and Indian dime novels. But the feeling around the neighborhood went deeper than the traditional prejudice against bookish youngsters. Jesse wasn’t just anti-social; he was anti-social in a weird way. There was something about the boy that was “not quite right.”

Nor was school the environment where he flourished. He was a good, but not necessarily outstanding, student. One teacher described him as “peculiar, intractable, not bad, but difficult to understand.” When he gave an answer, it was the answer. Jesse did not take kindly to any corrections. Nor was he a shame-faced recipient of punishment. He consistently displayed great bitterness and a stinging sense of injustice towards any disciplinary measures, no manner how minor or well deserved.

It’s a time-honored tradition for relatives of any weird criminal to finger some medical mishap as the turning point that sent the family lunatic to his or her gory rendezvous with destiny. For Jesse, this wasn’t the traditional bump on the head but a serious case of pneumonia he caught in October of 1871. During his illness, he went through many crises and was frequently delirious. Even after he recovered, his mother (whose irrational support and defense of her problem child was almost pathological) recalled that he remained “not so well.”

His first victims

Jesse celebrated his 12th birthday shortly after his recovery. A few weeks after he passed this milestone, it suddenly became very unpleasant to be a little boy in the Charlestown/Chelsea area. The first attack came around Christmastime. In Chelsea, a Boston suburb across the river from the Pomeroy home, an older lad enticed a small boy up to a remote area on Powder House Hill. As soon as they were alone, he forced the younger child to take off all his clothes and tied him to a beam. He then took a rope and, brandishing it like a whip, flogged the child into unconsciousness.

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In the months that followed, at least three more young boys in the Chelsea-Somerville-Charlestown area, most 7 or 8 years old, suffered similar, yet increasingly brutal and perverse assaults at the hands of the mysterious “boy fiend.” Lured to remote areas (generally Powder House Hill in Chelsea) he would force them to strip and bind them to a post or beam. He would beat them with a stick or whip them with a rope and force them to say naughty things like “kiss my ass.” Often, he cut them with a knife and shoved pins into their bodies. He paid special attention to the area around their eyes (mutilating their faces for life) as well as their genitals and thighs. Every one of the victims reported how much their brutal assailant enjoyed these torture sessions, jumping about with a smile on his face and laughter on his lips as his little victims writhed in pain.

Needless to say, the public objected loudly to these hi-jinx. The police were under considerable pressure to capture the perpetrator of these outrages. So far, the fiend’s victims had all survived, but it seemed only a matter of time before he went too far. The City of Chelsea offered a $1000 reward, and the police launched an aggressive investigation. Many a neighborhood bully found himself under suspicion. At least 17 youthful hooligans were arrested and paraded in front of the little victims. Each time, the battered little boys shook their heads. No, that wasn’t the boy torturer.

The attacks stopped as quickly as they began in late July. But by early August, another series of sadistic assaults on young boys started in South Boston. The modus operandi matched the Chelsea attacks. Victims were lured to lonely areas, generally by the shore or the train tracks, forced to strip, bound, beaten, and cut. By mid-September, at least three more boys had been assaulted.

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Meanwhile, things had not been going well in the Pomeroy household. Jesse’s father packed up and left, leaving Mrs. Pomeroy the daunting prospect of providing for their two boys. But she was a resourceful woman. She rented a small storefront in South Boston at 327 Broadway and made it into a dressmaking shop. And in August of 1872, the small family moved into a flat across the street at number 312. It wasn’t easy; both boys had to help out in the shop. Charles also took a job selling papers. Oddly enough, their move coincided almost exactly with the end of the Chelsea attacks and the beginning of the South Boston outrages.

Meanwhile, the boy torturer claimed his final victim on September 17. Using his undeniable gift for gab, he enticed a boy, apparently 5-year old Robert Gould, away from his home to a lonely spot near the railroad tracks. (No one can agree on the exact order of Jesse’s victims.) He forced the terrified child to strip, tied him to a telegraph pole, cut him about the face and whipped him.

The boy torturer had assaulted his last victim—at least for now. According to Jesse’s autobiography written a few years later, Jesse was innocently strolling by the police station a few days after the Gould attack when a cop walked out, accompanied by victim Joseph Kennedy. The cop beckoned Jesse to step inside. Jesse later wrote “I told him I had done nothing, and commenced to cry. I was so frightened.”

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At the station house, a few of the South Boston victims identified Jesse as the boy who’d attacked him. Jesse later begged to differ:

...those boys that had been so maltreated by another came and said that I was the boy that did it to them and the only way they identified me was because I had a spot on the right eye.

The police also suspected Jesse may have had a hand in the earlier attacks in the northern suburbs. They brought Johnny Balch down from Chelsea. Overjoyed, the small, now-scarred boy excitedly jumped about and exclaimed, “That’s the boy who cut me.”

Torturer on trial

When Jesse was indicted the following week, six of his erstwhile victims signed the complaint. At his trial, his mother testified that Jesse was dutiful, obedient, and an all-around “good son.” He never had problems with school and, contrary to that one neighbor’s story, was never cruel to animals. The whole thing came as a complete surprise to her. As for Jesse, he admitted all the charges, for now. (He would sing quite a different tune in the not-so-distant future.) Considerable sympathy was expressed towards Mrs. Pomeroy; even Jesse, whose lack of emotion was interpreted as an inability to comprehend the seriousness of his situation, cried after she testified. Nonetheless, he was sentenced to confinement for the duration of his “minority” at the Westboro House of Reformation. The judge had chosen this institution after much deliberation. He figured it was the place where Jesse would be least likely to contaminate other inmates.

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Life in South Boston returned to normal. Once again, small children darted recklessly along the sidewalks and through the alleys, no longer in fear of the lurking boy fiend. And Jesse went about becoming the star inmate of the reformatory. His behavior was impeccable. He applied himself to his studies, standing near the top of his class yet avoiding any difficulties with his fellow inmates. The administration granted him increasing privileges, eventually giving him free run of the entire school. And not once did he abuse fellow inmates or his newly won freedoms. The “boy fiend” had to all outward appearances reformed.

Thus, when his mother petitioned for his parole the following year, her request fell on receptive ears. Jesse was a model prisoner. A stable, healthy home awaited him, with plenty of work to distract him from the odd impure thought. Mrs. Pomeroy needed Jesse to help out in the store, and his brother could use an extra pair of hands on the paper route. The only concern was that Jesse might have some problems with the people in the neighborhood, especially from boys his own age. The local police put in their two cents here. They assured the reformatory that they’d be happy to keep an eye on things to make sure Jesse didn’t become a victim himself. It would be no problem.

The fiend on parole

Thus, about 14 months after his arrest, Jesse, now 14, was quietly paroled to his mother’s custody in early February, 1874. Just like the police promised, there were no problems. There was no outcry in the neighborhood or in the papers. Like a repentant sinner returning to the flock after going briefly astray, Jesse quietly went about his work, a testament to juvenile reform. He was ever the dutiful son.

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The quiet life of the neighborhood was disrupted briefly six weeks later. On March 18, 9-year old Katie Curran disappeared while running an errand on the 300 block of Broadway. The cops searched the entire neighborhood, including the Pomeroy store, looking for evidence of foul play. Fortunately for Jesse, a child told the police they’d seen a girl meeting Katie’s description climbing into a buggy with a strange man. The popular verdict was that she had been abducted. Jesse himself would opine the snatch had been arranged by her father in order to ship her off to a convent. Jesse was apparently never a serious suspect. Everyone knew he preferred little boys.

A little more than a month later on April 22, two boys playing in the marshes jutting out into Dorchester Bay between South Boston and Savin Hill made a grisly and gruesome discovery. They found the still warm body of a preschool boy lying on his back in the mud. He had obviously been the victim of a frenzied assault. His pants were down around his ankles. Blood still oozed from his eyes and numerous knife wounds in his chest and groin. Running, the boys told two nearby hunters of their discovery who then summoned the police.

It was a sight. The body was identified as Horace Millen, 4, of South Boston. His throat had been cut ear-to-ear, almost decapitating him. His body bore numerous stab wounds in his right eye, chest, and hands: all told, some 33 punctures. And, to leave no doubt as to motivation, the killer had all but castrated the boy. The testicles tumbled out onto the mud as the body was removed.

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Police found footprints nearby indicating an older boy had accompanied Horace to the scene of the crime. The footprints led back to a wharf a half mile away. Witnesses there remembered a young teenager that morning walking around with Horace, “asking what the men are shooting on the marsh.” He then jumped from the wharf, helping his small companion down with “a swing of his arms.” Horace took the older boy’s hand and, under what pretext will never be known, happily walked across the marshes to his fate.

This time, the police had a pretty good idea what kind of boy would do such a nasty thing. First instincts would prove correct. When they arrested Jesse at his home, they found blood on his knife, another spot of blood on his undershirt, and marsh mud on his boots. Reportedly, when the police confronted him with Horace’s mutilated corpse asked him if he’d done it, he laconically replied, “I suppose so.” Jesse explained he’d cleaned most of the blood on his knife by sticking it in the mud. His only request was that the police not tell his mother of his latest crime.

Whether Jesse actually confessed just then is open to question. Certainly, by the time of the inquest a few days later, he was singing a tune he’d harmonize with for the rest of his life: he was innocent. With utmost sincerity, he gave court a minute-by-minute account of how he rode the streetcars out to Boston Common for some good old-fashioned adolescent hanging-out the day of Horace’s murder. He hadn’t been anywhere near the marsh. The bloody knife? Why, that was the exact knife he’d lost earlier!

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For some reason, there was a long delay in setting a trail. Jesse was still lingering in jail in July, awaiting his day in court. And that is when it really hit the fan.

A terrible discovery

Things had been rough on Mrs. Pomeroy with her youngest son in jail. She continued to vociferously express her total belief in his innocence. Unfortunately, a son charged with capital murder wasn’t her only problem. Business at the dressmaking shop was bad and probably not improved by the increasing notoriety of the Pomeroy name. She was forced to close the store a month after Jesse’s arrest. She continued to operate out of her home.

One person’s misfortune is another’s good luck. James Nash, owner of an adjacent grocery business, saw this as a golden opportunity to expand. Mrs. Pomeroy had scarcely toted her dummies and sewing machine across the street when he signed the lease and started planning extensive renovations.

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In late July, a worker knocking down a wall in the cellar of the old dress shop noticed some bright fabric sticking out of a pile of ashes and rubbish. He reached down and gave it a tug. He received the shock of his life when a child’s skull rolled out of the rubbish. The police were quickly summoned.

After uncovering what was left of the body, the police had a pretty good idea who the corpse was. They brought in Mrs. Curran, mother of the girl that had vanished so mysteriously the previous month. The distraught mother identified the clothes as the ones Katie had been wearing the day she disappeared. The distressed woman exclaimed, “Oh, could she have been drowned. Anything, but such a death as this!” The police had to physically restrain her from taking remains, by now half skeleton, home with her.

Word of the discovery quickly spread through the neighborhood. No one had any doubts who might be responsible for this latest atrocity. A crowd gathered on the block, murmuring angrily about Jesse’s premature release and fomenting vague plans to do something. The police took Mrs. Pomeroy and Charles into custody, as much as material witnesses as for their own safety. It was not a good time on that block of Broadway to have the surname ‘Pomeroy.’

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At first, Jesse was indifferent when he heard news of the body. (He was really good at this.) But the police had a double cause for suspicion: not only had Katie’s body been found the Pomeroy store’s former quarters, Jesse had apparently been asking around the jail during the previous weeks if there was a reward offered for locating her body. When confronted with these accusations, Jesse coolly denied any knowledge of the body and called the stories lies that couldn’t be proven. He helpfully added that he didn’t think his mother committed the murder, either. In fact, the only thing that seemed to bother him was that she was in jail, too.

Jesse later confessed Katie’s murder to the Chief of Police. As he told the story then, Katie had gone out that morning to buy a “school card.” Stepping into the Pomeroy store by mistake, she asked Jesse, who was manning the counter alone, if he had any. Being a dressmaking shop, of course they didn’t. But Jesse, ever the boy fiend, hit on a scheme instantly:

I told her there was a store downstairs... I followed her, put my left arm about her neck, my hand over her mouth, and with my knife in my right hand cut her throat. I then dragged her to and behind the water closet... and put some stones and ashes on the body.

When a cop reading the confession back misread “cellar” for “stairs,” Jesse was quick to correct him. “I didn’t say ‘cellar’, I said ‘stairs’, for if I had said cellar she wouldn’t have gone down.” However, the surviving parts of Katie’s body bore mute witness to the fact that Jesse’s attack wasn’t so simple. She had been stabbed and mutilated much like the Millen boy. Later, when asked at the inquest why he’d done it, Jesse only said, “I do not know. I couldn’t help it. It is here,” pointing to his head.

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There were some questions raised as to how Katie’s body could have avoided detection all those months. As it turned out, the cellar of the store was a real mess. When the police checked it after Katie disappeared, they apparently took one look at the piles of junk and garbage, figured nothing had been disturbed recently, and left to search elsewhere. The tenants above the store later noticed a rank odor, but, as the papers described it:

They continued their search for defunct vermin in the crannies of the cellar and behind the ceiling, little suspecting the real cause of their inconvenience.

Although contemporary accounts make no mention, the smell may have played no small part in the failure of Mrs. Pomeroy’s dress store.

A high-profile murder trial

In December, Jesse was tried for the Millen murder. Two doctors for the defense testified that Jesse was insane due to some obscure form of epilepsy. To no one’s surprise, another doctor brought in for the state thought that while Jesse certainly wasn’t normal, neither was he crazy. However, all three medical men concurred on two things. Jesse had no feelings for his victims and felt no remorse for any of his acts. The jury convicted him of first degree murder with a recommendation of mercy despite this unflattering diagnosis. But the judge brushed aside their advice and sentenced Jesse to the gallows anyway.

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This set off another storm of controversy. Many prominent men, including Oliver Wendell Holmes, supported commuting Jesse’s sentence to life imprisonment on the basis of his tender years. He’d barely turned 15, after all. A commutation petition was quickly filed. But hot on its heels came a counter-petition, “numerously signed by both sexes protesting against it.” In the midst of this furor (which wasn’t helped when church sexton Thomas Piper luridly clubbed a small girl to death in a Boston belfry), the state’s Executive Council formally denied Pomeroy’s petition for clemency. The governor needed only to sign a death warrant and set a date to make Jesse only the second child under 16 executed in Massachusetts history.

While the governor pondered, Jesse’s autobiography was serialized in a local newspaper. In keeping with a rich tradition in criminal autobiography, Jesse denied all charges against him. His early young victims were all mistaken in their identification:

Not one of them did or could tell what dress I wore or how my voice sounded—in fact, failed to notice everything a sharp boy would and fell back on the untenable ground of identifying me by my eye.

His original confession came only after being dragged out of bed around midnight and being threatened with “prison for 100 years” (wich we shall see was not that much of an exaggeration). His first trial, why, it was no trial. “The complaints were read to me, and I understood them about as much as I would Greek or Latin.” And his conviction? “It was not justice dealt out, but rather injustice.”

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He was equally glib in discounting the two murders. Confessions be damned. He accounted for his activities on the day of the Millen killing minute by minute. Needless to say, he wasn’t anywhere near the marsh. He only confessed and feigned insanity to protect his mother and brother, who had spent five and six weeks in jail respectively. The jury that convicted him consisted of “12 jackasses good and true.”

But no one, not even Jesse himself, had as much faith in his innocence as his mother. In letters published in the papers, she repeatedly stated her unshaken belief in her youngest child’s complete innocence. She knew Jesse, ever the selfless son (“...there never was a more kind-hearted boy”), confessed only to save her: “I was not surprised—I knew Jesse better than anyone and I knew his generous heart...” She bemoaned the cruelties heaped upon her innocent offspring: “I do not doubt that he is insane—driven insane—driven insane by the treatment that was heaped upon us.” She knew that Katie’s body had been put in the cellar after she vacated the store, and much of the testimony and evidence against Jesse was either contrived or misinterpreted. She angrily blamed Jesse’s death sentence as a sop to appease the bloodthirsty mothers of Massachussets.

Meanwhile, the governor wouldn’t sign Jesse’s death warrant. And when a new governor was elected, he too refused to sign on the dotted line. The Executive Council finally caved in. On August 31, 1876, Jesse’s sentence was commuted to life in solitary confinement.

Prison life

Jesse was transferred to the State Prison at Charlestown. His home for the next 16 years was a boiler-plate lined 10’ x 8’ x 8’ “coke oven” cell built in 1805 to house the insane. Isolated from the prison population, he came in contact with no one save his mother (who visited every month until her death in 1914), prison officials, and perhaps the odd clergyman and a lawyer or two. In the early 1900s, he was transferred to a more modern, but no less solitary, cell.

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Jesse did not spend these years of isolation quietly going insane. Number one item on his agenda was escape. Every couple of years, the papers carried stories about his latest effort, which generally never went too much beyond monkeying with the bars. The only notable effort was in 1888, when he dug a small hole through the wall of his cell, broke a gas pipe, let the gas fill the gap between two walls, and lit a match. Typical of his escape schemes, the resulting explosion did not blast out the wall or tear his cell door open. He succeeded only in singing his eyebrows and making a lot of noise. Jesse never came close to busting out of the joint.

Between escape attempts, he became an omnivorous reader and fanatical self-educator. He eventually read all 8000 books in the prison library, picking up a working knowledge of a broad range of subjects and learning several languages, including French, German, Greek, Latin, Spanish, and Italian.

Not too surprisingly, one of his favorite subjects was law. If Jesse couldn’t get out one way, he’d do it the other. Over the years, with no official encouragement or the faintest glimmer of a positive response, he bombarded every authority from the Governor to the US Supreme Court with a steady stream of petitions, briefs, and pleas. The arrival of his petition for pardon at the state capitol in Boston was almost an annual event. No less than 12 governors in a row would deny it.

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Jesse may have been bettering himself intellectually, but he was far from Nathan Leopold material. A commission of three psychiatrists and the prison physician studied him and reviewed his case in 1914 after he’d spent 38 years in solitary. They found him to be sane and intelligent, but a cold, paranoid manipulator utterly obsessed with his pardon. Their report stated:

He takes kindness as a matter of course, is highly egotistical and inclined to dictate to the prison authorities. His only interest in his mother is the aid she can give him in securing his release. He shows no pleasure at seeing her but begins on his case as soon as she comes and talks of nothing else. He is very unreliable on account of his untruthfulness. He thinks everyone is against him and apparently never loses his suspicions for a moment.

Surprisingly, they found Jesse a strong believer in firm punishments for law breakers. But when conversation turned to applying this theory to his case, he became evasive and steered conversation to the “illegality” of his sentence. The commission noted, “His memory is very good except on points the admission of which might weaken his case.”

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In 1916, the Executive Council finally voted to lift Jesse’s solitary confinement. For the first time in 41 years, he was allowed to attend chapel, mingle with the general population, and work in prison industry if he so desired. Not that he did. Commissioner of Corrections A. Warren Stearns, who knew Jesse, wrote in a long article on the case:

He engaged in no occupation, never participated in prison industries, and was seen as a gradually aging old man, nearly blind, with a tremendous hernia, standing about impassive and solitary, not taking part in any of the social life of the institution.

The Boy Fiend as an old man.

Gradually, Jesse became the most famous convict in the country. In 1920, when he made his first public appearance since boyhood, it was headline stuff. At the annual inmate minstrel show, he read a 13 stanza poem, one of many pieces he contributed to the prison newspaper under the byline ‘Grandpa.’ Convicts and staff accorded him a standing ovation.

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Later that year, he privately published his first (and apparently only) book, Selections from the Writings of Jesse Harding Pomeroy. Reportedly, friends from his boyhood (!) helped him pull this project off. Comprised of a mix of poetry and prose pieces with stimulating titles like “How I Learned Spanish”, “A Boston Brew of Tea, Sir!” and “A La Miss Suffragette”, a reviewer concluded that although not bad, “there is nothing in his book of intrinsic merit.”

The milestones gradually passed. The judge at his trial, the prosecutor, his lawyer, and all 12 jurors died. His mother visited him every month until her death around 1915. Clarence Darrow threatened to take up his case, blustering, “The State of Massachusetts ought to be in the hands of a receiver for keeping Jesse Pomeroy in prison 50 years. It is an outrage.” But nothing further came of this. By the late ‘20s, Jesse was the state’s oldest prisoner.

Despite his anti-social attitudes, Jesse found plenty to keep himself busy in between his never-ending pleas for a pardon. In 1927, one Miss Alice Blackwell wrote a letter to a Boston paper accusing Jesse of being cruel to animals in prison. (This was the subject of many a popular rumor. Prison records, however, record no such offenses.) Jesse was severely offended by this affront to his good reputation. He responded by suing her for libel. The presentation of his case at the trial was hampered by prison officials refusing to give him a furlough to testify on his own behalf. Nonetheless, he won, but it was a hollow victory. He was only awarded $1 in damages.

End of the line

In 1929, the warden recommended Jesse for transfer to the State Prison Farm at Bridgewater. Jesse protested vociferously. The only ways he planned to leave Charlestown were via pardon or pine box. He added petitions to block the move to his usual pardon paperwork. But it was all for naught.

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The transfer came through in August. Jesse was driven to Bridgewater, his first real ride in an automobile (he’d had one quick spin around the prison yard a few years earlier). Virtually every two-bit pen jockey in the country seized the opportunity to comment on how strange the outside world must seem to this modern Rip van Winkle after 53 years “inside.” Poor Jesse unwittingly found himself the spring board for countless bad metaphors and half-baked musings on 50 years of progress.

During the extensively documented 1 hour, 43 minute transfer, the 69-year-old murderer appeared very shy and unsure of himself. The crowds and the traffic frightened him; he pulled his cap down and coat up to conceal his face as much as possible. He saw his first elevated train and his first steam shovel. In wonderment, he asked where all the horses had gone. Even though he was now blind in one eye and losing sight in the other, he noticed a headline trumpeting the move of the “boy slayer.” He questioned why they were making such a big deal about it. And why did they insist on calling him “slayer”? He drank ginger ale, ate an ice cream cone, and watched a plane take off. Left unsaid were his thoughts on the young boys he surely saw on the streets.

At Bridgewater, Jesse became even more “dissatisfied, peevish, almost surly.” Losing his cell behind Charlestown’s austere brick walls and iron bars knocked him from his spot as America’s most famous convict. He’d had prestige and special privileges at the State Prison (he used to sell photos of himself for $1.50); now he was just another old codger out on the farm. He had little to say to anyone, and didn’t take part in any activities. When they caught him with a bundle of tools and clothes for one last escape attempt, everyone laughed, sure the 70-year old con was just out for the publicity. With his hernia reaching massive proportions, he’d be lucky to make a half mile even without pursuit.

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Jesse died two years later on September 29, 1932, two months shy of his 73rd birthday. By then, he’d spent a record-setting 59 years in jails, reformatories, and prisons, much of it in solitary confinement. After his death, there were rumors that he had amassed a considerable fortune from his writings, his brokerage account, and his photo-peddling business. But when they actually got around to counting it, he’d only left an estate valued at $191.

In the years following his death, a small body of legend grew up around him. Some accounts claimed he’d killed dozens of children. Others stuck to the traditional two victims, but hinted darkly he’d tortured many more children who never came forward. Accounts of his 1888 gas-fueled escape attempt became exaggerated to the point where three fellow inmates were killed in the blast, and so on.

But even with the case shorn of its legends, the remaining facts are enough for Jesse to occupy a high position among the ranks of youthful offenders. He is unmatched for his cruelty and continuity. His crimes weren’t the behavioral lapses of some little brat, but the vicious acts of someone who loved what he was doing. The only thing that stopped Jesse was getting caught; chances are, if he’d gotten out again, he would have been up to his old tricks again within weeks. Jesse truly deserves his naughtiest boy crown.

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Lower image: AP Photo

John Marr is the former editor of the zine Murder Can Be Fun. Further information here and here.

This article originally appeared in Murder Can Be Fun and has been republished with permission.