Other historians of crime, however, have seen Jesse’s experience in a very different light. According to these writers, Jesse never lost his sanity during his decades in solitary for the simple reason that he had none to lose—i.e., that he was criminally insane to begin with. These experts view Pomeroy’s unremitting struggles against his captors, not as a sign of his heroic willpower, but as the symptom of his monstrously warped, hopelessly incorrigible nature. In a Boston Globe article that appeared in 1932, for example, a writer named Louis Lyons described Pomeroy as “the meanest prisoner” in the history of Charlestown:
He could not be trusted a minute. He would steal from other prisoners. A moral degenerate, a pervert, a sadist, his traits persisted through the years. Even at the State Farm, young lads had to be kept away from him. . . . He never responded to kindness, was always suspicious of everyone, and never showed any interest even in his mother, who martyred herself to seek his freedom through forty years. He never would talk to her about anything except his case and her efforts toward his release. . . .
Obsessed with his importance, he was forever demanding hearings, pardons, commutations, forever complaining, forever seeking publicity by any means, never ceasing to insist on his martyrdom.
However one views Pomeroy—as a resolute, unyielding freedom-seeker (a kind of homegrown Papillon) or a sociopathic monster forever contriving diabolical ways to break out of his cage (a sort of real-life Hannibal Lecter)—one fact is incontrovertible. From virtually the moment that he entered the grim fortress of Charlestown until the day, fifty three-years later, that he was finally transferred to the State Farm at Bridgewater, Jesse Pomeroy was a persistent, rankling, irredeemable source of trouble for his captors.
* * *
The “punishment books” from the years of Jesse Pomeroy’s confinement in Charlestown can be found today in the vaults of the Massachusetts State Archives in Boston. These enormous ledgers—fourteen in all—record the transgressions of each prisoner, along with the sanctions meted out (typically, a day or more locked up in the “strong room,” a lightless isolation cell in the basement).
These bare-bones entries offer a revealing glimpse of the exceptionally strict discipline enforced at the penitentiary—of the harsh penalties imposed for even the most trivial reasons. Indeed, for the most part, the infractions noted in the books seem no more heinous than the misdemeanors of unruly high-schoolers. In any given year, the average inmate might have committed one or two offenses, the most common of which were “disobeying orders,” “insolence to officer,” “refusing to work,” “bad conduct in hall,” “smoking in cell,” “talking in cell,” “singing in cell,” “talking on line,” “fooling in corridor,” and “fighting in shop.”
Jesse Pomeroy’s record, however, is of a strikingly different order. A typical yearly entry for a prisoner in Charlestown, for example, reads as follows:
JOHN LOFTUS
DATE
OFFENSE
Jan 26, 1886
Disobedience
Mar 8
Laziness
May 5
Profanity
Oct 26
Not doing his work
Dec 1
Refusing to go to shop
By contrast, Jesse Pomeroy’s entries from November 9, 1877, through 1912 are as follows:
DATE
OFFENSE
1877
Nov 9
Trying to escape, digging through cement
Apr 18
Cutting bars in cell
1880
Nov 2
Cutting iron work of cell
1887
Sept. 4
Attempt to escape, cutting bars of cell door
Nov. 10
Causing gas to explode in cell
Dec. 26
Tampering with cell door
1888
Jan 10
Digging in his room
May 29
Cutting cell door, having tools in his room
1891
May 25
Cutting cell door
Aug 17
Attempting to escape, cutting bars in cell
window
1892
Aug 14
Cutting cell door
Aug 25
Cutting cell door
Oct 17
Attempting to escape
1894
Jan 26
Digging bricks out of the wall of his cell
1895
March 9
Cutting bar in cell window
July 25
Digging around cell window
1897
Jan 6
Attempting to escape
Feb 8
Digging a hole in the floor of cell
1898
Sept 6
Cutting cell door
1899
Feb 3
Cutting cell door
June 26
Cutting cell door
1900
Oct 26
Cutting iron work in cell; attempting to escape
1904
Aug 7
Digging around the water pipe in his cell
1912
Dec 30
Cutting bars in cell door
Cut-and-dried as they are, these notations serve as an eloquent testimony to one of Jesse Pomeroy’s most remarkable qualities—the trait that kept him in the public spotlight throughout his lifetime, and that has earned him a special place in American penal history. For fifty years—with a persistence that was either insane or undaunted (depending on your point of view)—Pomeroy never gave up his efforts to dig, cut, detonate, or bore his way out of his cell. Even the Boston Globe—a paper that never failed to portray him in the most fiendish light imaginable—seemed perversely proud of the fact that, in the person of Jesse Pomeroy, New England had produced “the most ingenious . . . and utterly tireless worker for freedom who ever occupied a cell.”
* * *
According to prison records, the first of Jesse’s more than two-dozen jailbreak attempts occured in November 1877, slightly more than a year after he was first locked up in Charlestown. Patrolling the arch of the west wing—the section of the prison where Jesse was initially housed—a guard heard a faint scraping sound emanating from Pomeroy’s cell. Throwing open the door, he found the prisoner kneeling by a wall, working away at one of the stones with a little digging tool made from a bit of wire. Apparently, Jesse had been engaged in this enterprise for months. When the guard took a closer look, he discovered that—by painstakingly removing the surrounding mortar, a grain at a time—Jesse had actually managed to loosen the stone.
Five months later, Jesse was caught sawing at the iron bars of his cell door with a piece of sharpened tin. For this attempt, he was shut up in the dark, nearly airless “strong room” for a week. But nothing—no amount of time locked in a dungeon, no beatings administered with a brass-tipped cane, no efforts at reinforcing his cell—discouraged Jesse for long. When plates of boiler-iron were bolted to his walls to keep him from digging at the stones, he set to work prying loose the bolts. When the walls were painted with a white preparation that would make even a pin-scratch conspicuous, he turned his attention to the floor, cutting loose one of the heavy boards, then digging at the ground underneath.
The singleminded tenacity Jesse displayed as a jailbreaker was matched by his mechanical ingenuity. Over the course of fifty years, virtually everything that fell into his hands became a potential implement of escape: eating utensils, drinking cups, writing implements, slop pails, bits of tin, wire, and string. When he was finally permitted a few hours of solitary exercise every week in a small, enclosed yard, he would scour the ground for anything useable—a rusty nail, a metal scrap, a piece of wood. With these and other objects (including the occasional knife blade or steel spike smuggled to him by a sympathetic fellow prisoner) he managed, over the decades, to fashion an amazing assortment of tools: awls, chisels,
saws, drills, files, pry bars.
One of his most spectacular escape attempts occurred in November 1887, just two months after he was caught in an attempt to saw through the iron bars of his cell window. At around 1:00 P.M. on Thursday, November 10, an enormous explosion rocked the west wing of the prison. Revolvers drawn, guards rushed to the scene. Outside Jesse’s cell, the corridor was thick with smoke, plaster dust, and the smell of escaping gas. Throwing open the door, they found Pomeroy crumpled in a corner, his face badly singed. A huge block of granite, dislodged from the ceiling, lay in the center of the floor—vivid testimony to the power of the blast.
Transported to the prison hospital, Pomeroy remained unconscious for nearly an hour until the physician, Dr. Charles Sawin, managed to revive him. Jesse’s eyebows and eyelashes were entirely burned off and his lids badly swollen. Early reports declared that he had been “totally blinded,” though he soon recovered the full use of his one good eye. Eventually, he supplied his captors with the full details of his latest and most audacious plan.
By that point in his sentence, Jesse was allowed to leave his cell for forty-five minutes of exercise three times a week. Always vigilant for anything he might turn to his advantage, he had noted that the dim gas-lights in the corridor were fed by a pipe that ran along the upper wall just outside his cell. Day by day for the next several months—working with nothing but a sharpened scrap of tin and infinite patience—he had dug a little opening through the mortar in his cell wall, concealing each day’s progress with a paste made of soap. Eventually, he had broken through to the other side at a spot directly beside the gas pipe. Then, with a piece of wire sharpened to a fine point, he had bored a little hole in the pipe, releasing the gas through the opening in the wall and into his cell. Working quickly, he had taken a makeshift length of tubing, constructed of water-soaked newspapers mixed with bread, and piped the gas to another portion of the cell, where he had loosened several blocks after months of painstaking toil. His idea was to feed the gas through the crevices he had created in the stonework and blast a hole in the wall.
In the end, this elaborate—if wildly ill-conceived—scheme had no other effect than to injure Jesse, damage the floor of the prison hospital (located directly above his cell), and trigger a fresh burst of public outrage. Jesse’s jailbreak attempt—his second in as many months—was reported in newspapers throughout the country, though it created the greatest sensation, of course, in Massachusetts. One Boston man voiced a common sentiment when, in a letter to the Herald, he expressed his “regret that the ‘boy fiend’ didn’t get his body through the wall so that the keeper might have had an excuse to shoot him and forever rid the world of him.”
This letter is striking for several reasons. It reveals not only the deep, abiding antipathy toward Pomeroy among the citizenry of Boston, but also the extent to which he had achieved a kind of mythic status. In the perception of the public, Jesse Pomeroy was still—and would remain for many years—the monstrous “boy fiend.” (Indeed, several generations of New England children would grow up hearing bedtime spook-stories about this legendary, juvenile bogeyman.)
In reality, of course, Pomeroy was far from a boy. In November 1887, when this letter was written, he had been locked in solitary confinement for more than a decade and was already twenty-eight years old.
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There can be no doubt that the most interesting convict in the Commonwealth of Massachusetts, if not the whole country, is JESSE HARDING POMEROY. He is the only convict in the United States who is absolutely consigned to a cage, and who is looked upon by the community as a veritable fiend.
—E. Luscomb Haskell, The Life of Jesse Harding Pomeroy (1892)
By 1892—following the renovation of Charlestown—Jesse was inhabiting a larger (if equally cheerless) cell in a section of the prison known as “Cherry Hill.” He was no longer engaged in making scrub brushes—or in any other task, for that matter. All such menial labor, he claimed, was injurious to his health and therefore a violation of his constitutional rights. Since Jesse was in the habit of squirreling away little bits and pieces of his work material and using them in his endless escape attempts, the prison officials had no objection to relieving him of his duties.
With nothing but time on his hands, he devoted himself to other activities. With supplies provided by the chaplain, he tried his hand at painting, producing mawkish watercolor landscapes that he regarded as significant works of art, though at least one observer found them “hardly worth admiring.” Always mechanically inclined, he conceived of a hollow, self-sharpening lead pencil, but his efforts to construct a workable prototype came to nothing. Most of all, he spent his time reading. Since sensationalistic novels were in short supply in the prison library, he was forced to make do with more uplifting material—books on science, mathematics, language, chemistry, and religion. According to various sources, by the time he left prison, Jesse had gone through all four thousand books in the library, along with an indeterminate number of volumes supplied by the chaplain.
Though reports of his intellectual accomplishments would be greatly exaggerated (for years, stories would circulate that Jesse had proved to be a jailhouse genius, who achieved proficiency in Hebrew, Greek, and Latin, taught himself geometry, algebra, and calculus, and became an expert on classical literature), he did, in fact, pick up a smattering of knowledge in several fields and gained enough mastery of several languages, particularly German, to be able to read them with a fair degree of fluency. (He was never able to speak them, since—deprived of virtually all human communication—he had no way of learning the correct pronunciation.)
He also put in a good deal of time studying law books.
As far back as 1876, when he composed his autobiography while languishing in the Suffolk County jail, Jesse had shown a certain knack for legalistic argument. Now, after immersing himself in every law book he could get his hands on, he acquired just enough knowledge of the subject to turn himself into a source of endless annoyance—an incorrigible gadfly. Next to his improvised drills, saws, and chisels, Jesse’s pen became his primary tool for making life as difficult as possible for his keepers.
For fully half a century, he generated hundreds of letters, writing to everyone from district attorneys to members of the prison board to justices of the United States Supreme Court (including Oliver Wendell Holmes). Jesse’s term in Charlestown would span the administrations of no less than twenty-two Massachusetts governors—and every one of them was bombarded with correspondence from Pomeroy. Many of these letters registered various complaints. Like other psychopaths—who tend to be full of self-pity, however incapable they are of feeling bad for their victims—Jesse constantly felt ill-treated by his jailers. In letter after letter, he griped about everything from the poor light in his cell to his lack of holiday privileges to the deplorable condition of his toothbrush.
Other letters were, in effect, fairly sophisticated legal briefs. In 1888, for example, while poring over some old law books, he discovered (as the New York Times reported) “an old statute which provided that no person should be sentenced to solitary confinement in a prison for a period of more than twenty days.” Jesse immediately began petitioning for his release from solitary. Dozens of these letters still exist in various archives. The following, dated October 14, 1888, is a typical example. Addressed to Henry B. Pierce, Secretary of State of Massachusetts, it was written on lined, monogrammed notepaper and penned in the neat, even elegant handwriting that Jesse had by then developed:
Sir,
Certain laws, records, etc., necessary to my right of self-defense, and necessary to properly present the same are on file in your office, and I understand that the law permits me copies of them.
Within is an expression of my wants and I declare that I believe them to be necessary to me as above stated. I ask of your courtesy such a fulfillment, certified under your seal as the laws permit.
I ask,
1. A copy of the revised statutes of this state in f
orce in 1874.
2. A copy of the acts and resolves of the Legislature in 1874.
3. Literal copies of all the laws passed by our Legislature at any time, which regulate the punishment of close or solitary imprisonment or confinement, provided it is a punishment for crime.
4. If this request is too vague and causes too much trouble, please give me only what was the law on the subject in 1806. 1845. 1855. 1874.
5. Literal copies from the record of the Governors Council of all entries therein showing executive action in any way upon my case, from March 1875 to Sept. 1st, 1876.
Please observe, I want records of executive action only: nothing about trials, indictments, etc.
6. Literal copies from the records of the Council from 1780 to 1875 inclusive, showing commutations to the penalty of solitary or close imprisonment or confinement with—or without—hard labor: and pardons or commutations of those penalties.
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