Hard work, discipline and vocational training were the preferred methods of dealing with juvenile delinquents in the late 1800s. The Westborough House of Reformation was the place where miscreant boys of all ages were sent if they were convicted of a crime. It was also a place where parents who found their boys too hard to manage could voluntarily commit the troublemakers.

Westborough was a cruel place where the strong preyed on the weak. The discipline was harsh and whether the House of Reformation could actually claim to live up to its name of reforming youthful offenders was debatable. The inmates were expected to work most of the day on tasks such as brass nail making, chair caning and silverplating, and then were subjected to a four-hour school day.     

Discipline was along military lines. Despite the attempt at reform and a more humane approach to treatment than in earlier times or in adult institutions, in any closed system where social deviants are incarcerated, a jungle-like mentality emerges.

In this environment, a smart, cruel boy like Jesse Pomeroy could flourish. Most of the boys who had been sent to Westborough were non-violent offenders, Schechter reports, citing the massive “History of Boys” -- the volume that detailed the relevant details of every inmate ever sent to Westborough. The most frequently cited crimes were shoplifting, breaking and entering and the vague "stubbornness."

Jesse learned very quickly that his only chance to leave Westborough before his 18th birthday was to demonstrate that he had reformed his ways. The records show he was a model inmate, who avoided the floggings and corporal punishments meted out for even the most minor infractions.

They chronicle that he took an unusual interest in those punishments, often seeking out the most recent recipients to extract the painful details. The history of Westborough also reports that Jesse was mostly left alone during his sentence; the older boys teased him and the younger boys, who all knew why he was there, gave him a wide berth.

Shortly after he was brought to the reformatory, Jesse was taken out of the chair shop and assigned as a hall monitor. He thrived in his position of authority, taking great pleasure in maintaining order in his dormitory.

His time at the reformatory was quiet; he even opted not to join nearly half the inmate population who used an unlocked door to escape one afternoon.

There was that one incident, however. It happened toward the end of 1873, when Jesse had been in the reformatory for more than a year. He was outside when a teacher approached him and reported seeing a snake in the back garden. She asked for his help in killing it.

"Eager to oblige, Jesse had followed her back to the garden, snatching up a stick along the way," Schechter writes. "After a brief search, he uncovered the snake and began to strike it again and again, working himself up into a kind of frenzy as he reduced the writhing creature to an awful, oozing pulp."