Boston was a thriving city in the late 19th century when Jesse Pomeroy was born in 1859, the second son to Charles and Ruth Pomeroy, a lower middle class family in the city's Chelsea section. The Pomeroys were not a happy family. Charles drank and had a mean temper. He once used a horse whip on young Jesse when the boy played truant.

A trip behind the outhouse to the young Pomeroy children meant a savage beating that often ended in bloodshed. Charles Pomeroy would strip his children naked before a beating, somehow helping Jesse forge a link between sexual satisfaction, pain and punishment. Jesse would later recreate his father's abuse on his young victims.

The Pomeroy family was unable to keep pets in the house because strange, violent things seemed to happen when no one was looking. Harold Schechter reports that Ruth Pomeroy had wanted a pair of lovebirds to brighten up the dreary home, but she feared what would happen to them. The last time the family had birds they both ended up dead, their heads completely twisted off their bodies. After Jesse was discovered torturing a neighbor's kitten, there was no way Ruth would allow another pet into their home.

Like many killers, Jesse Pomeroy grew weary of torturing animals and began to look for human targets. Naturally, he selected victims who were smaller than himself. His attacks had an eerily familiar appearance; he acted out and enhanced what he experienced at home.

His first known victim was William Paine.

Near Christmas Day 1871, two men lumbered up Powder Horn Hill near the Chelsea Creek in South Boston. Nearing a small cabin, they heard a soft cry, barely louder than a whimper. As they approached the building, really nothing more than an outhouse, Schechter reported, the sounds grew louder and clearer. It was a small child.

Entering the building, the men were shocked by what they saw. Billy Paine, no more than 4 years old, was hanging by his wrists from a rope lashed to the center beam of the outhouse. He was nearly unconscious and half-naked. The cold weather had turned his skin pale and his lips blue. His hands, purple due to the blood trapped by the bindings, stood in sharp contrast to the rest of his shock-whitened skin.

The men quickly cut the boy down but not before gasping at the signs of the brutal beating young Paine had suffered. His back was covered in welts, red and ugly against his flesh.

Billy was in no condition to give police any clue to the identity of his attacker, and the police filed the awful report with the fervent prayer that it was an isolated incident.

Sadly for the children of Chelsea and South Boston, it wasn't.

In February of 1872, Tracy Hayden, 7, was Jesse Pomeroy's next victim, and he was lured to Powder Horn Hill with the promise of "going to see the soldiers," according to Schechter.

Once the two boys were alone, Pomeroy, who was barely a teenager at the time, set upon the diminutive Hayden and bound and tortured him as mercilessly as he had Billy Paine. Hayden's front teeth were knocked out, his eyes blackened and his nose broken by the enraged Pomeroy.

Like Billy Paine, Tracy Hayden was stripped and whipped with a switch, leaving deep welts, and Hayden told police that his assailant, whom he was unable to describe other than having brown hair, threatened to cut off his penis.

With nothing more to go on than a description of a teenage boy with brown hair, police were powerless to stop the assaults. But they knew they had a deviant on their hands and they could only assume that he would strike again.

In early spring 1872, Jesse attacked again. This time, promising 8-year-old Robert Maier a trip to see Barnum's circus, Jesse took the boy across the fens to his favorite lair and attacked. Stripping Maier and beating him with a stick, Jesse forced the youngster to repeat curse words as he was assaulted. Maier reported to police that Jesse was fondling himself as Maier withstood the ferocious beating. Achieving sexual satisfaction at the height of Bobby's suffering, Jesse freed the youth, threatened him with death if he told anyone and fled.

The police, faced with numerous angry and fearful Boston parents, began a massive manhunt, questioning hundreds of brown-haired south Boston teenage boys, with no luck. The "inhuman scamp," as the papers called the unknown pervert, eluded the dragnet, and became almost a bogeyman to the youngsters of the city. Parents warned their children not to talk to any strange boys and, as word spread, an inaccurate description replaced the one police were using: the new assailant took on a devilish appearance, now described as having red hair and a wispy red beard. Unbeknownst to anyone, the real monster, Jesse Pomeroy, at 12, was as smooth-skinned as a young girl.