I declare these last two requests to be absolutely necessary to me to be granted, and I ask that all papers embraced in the 6th request be certified under seal, because I intend to lay them before the Supreme Court.
I can assure you, Mr. Secretary, that my need is great and is my only excuse for so much asked for.
Very respectfully,
Jesse H. Pomeroy
Thanks to this and scores of similar letters, Jesse eventually earned a reputation not only as a scholar of classical languages, literature, and mathematical knowledge but also as a self-educated lawyer—a man who (as the Boston Globe put it) “had developed legal qualifications not possessed by some applicants for admission to the bar.”
* * *
Between his jailbreak attempts and legal maneuverings, Jesse managed to maintain his notoriety as the century drew to a close. In 1892, a full-length true-crime book—E. Luscomb Haskell’s The Life of Jesse Harding Pomeroy—became a popular seller, confirming the public’s ongoing fascination with the case. Two years later, when a writer for the Boston Globe managed to interview Jesse, the story created a sensation.
Exactly how he finagled the interview isn’t clear, but on the afternoon of Thursday, June 2, 1892, the unnamed reporter—who was visiting Charlestown on unrelated business—talked his way into Pomeroy’s cell, where he held a thirty-minute talk with the “world’s criminal of criminals” under the watchful eye of a guard. At that time, Jesse was forty-two years old: a compact, square-shouldered man of medium height, dressed in the usual convict garb—trousers, shirt, and jacket, all of coarse gray wool. His hair was receding, he wore a walrus moustache, and his deformed right eye—whose pale, filmy surface looked to the reporter “like a white cloud in a bleared window”—had lost none of its deeply unsettling power.
Jesse—who hadn’t spoken to a stranger in thirty-six years—seemed extremely ill at ease at first. Perched on the edge of his table, he chewed on a corner of his droopy moustache and refused to say a word. Finally—when the reporter asked whether he had any complaints—Pomeroy twisted his mouth into a snarl and replied, “I don’t complain. It does no good.” Then, shooting a murderous look at the hovering guard, he added: “They don’t make my life any too pleasant to bear, and to tell anyone about it only makes it worse.”
In spite of this remark, however, Jesse’s comments to the reporter consisted largely of complaints. He grumbled about the poor light in his cell, which made it hard for him to read; about the confiscation of the Christmas “goodies” sent by his mother; about the lack of sufficient exercise. When the reporter asked about food, Jesse barked a laugh. It didn’t seem right to complain, he replied, since he had gotten “fat as a pig” in prison (indeed, as the journalist noted, the former “boy murderer” had grown into a distinctly paunchy adult). Still, though he was given “plenty of food to eat,” its flavor and variety left a lot to be desired—though he supposed that the unappetizing sameness of his meals was “part of the punishment.”
When the guard signaled an end to the interview, the reporter rose from his chair and asked Jesse if he had anything more to say. At first, Pomeroy merely shook his head. Then—fixing the reporter a look of “fierce” determination—he declared that he still planned to get out of prison someday. By one means or another.
Following the interview, the reporter spoke to several of the officers, gleaning additional facts about the prisoner. He discovered that—though Jesse had read many of the books in the library, some more than once—the Bible wasn’t among his favorities. Indeed, on one occasion, a guard heard such uproarious laughter coming from Jesse’s cell that he went to the door to see what so funny. He found Pomeroy reading the Bible with a broad, jeering grin, “as much as to say, ‘I don’t believe a word of it.’ ” Even the prison chaplain—a man of such sweet disposition that he was beloved by virtually all the inmates—had become so put off by Jesse’s flagrant disdain of religion that he seldom visited Pomeroy’s cell anymore.
The reporter also learned that, at one point, Jesse had taken up the “mouth-harp.” Unfortunately, the only song he had learned was “Home, Sweet Home,” a tune he played so often that the guards were nearly driven crazy. Finally, they decided to confiscate the instrument. When they entered his cell, however, they discovered that Jesse had already taken the harmonica apart and made one of the metal pieces into a little saw.
As for his escape attempts, the guards didn’t take them very seriously, regarding them as little more than Jesse’s way of causing “deviltry.” He would never make it out of the prison. Even if he managed to break out of his cell, he wouldn’t get far—“for the orders are that he shall be shot without hesitation if he once gets into the yard.”
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Jesse Pomeroy, the boy-murderer of 20 years ago, the fiend whose crimes were even more revolting than those of Jack the Ripper, and whose name has always brought to mind all that is repulsive, blood-curdling, and inhuman, has evidently not given up hope that some day he may escape from the Charlestown State Prison.
—The Boston Globe, September 29, 1893
Until the day he finally reemerged, Lazarus-like, from his vault, Pomeroy continued to make so many attempts at breaking free that only the most spectacular were reported in the press.
On January 8, 1897, for example, the Boston Globe ran a front-page story headlined “JESSE POMEROY AGAIN TRIES TO ESCAPE. Only 24 Inches Between the Prisoner and His Freedom.” The previous Wednesday, a prison guard named Eugene Allen—peering into Pomeroy’s cell through the little slot in the outer door—had seen him pacing nervously around the floor. There was something so odd about Jesse’s overwrought manner that Allen immediately ordered him out of the cell, removed its bare-bones furnishings, and began to conduct an inch-by-inch search.
After satisfying himself that the white-coated walls had not been tampered with, Allen turned his attention to the floor. Armed with a case knife, he inspected every crack in the wooden boards, beginning at the threshold and working his way back across the cell. He was about two feet away from the rear wall when the blade of his knife suddenly slipped through an apparent joint in the flooring. Frowning, Allen took a closer look—then let out a little grunt of surprise. What he’d taken for two boards connected by a joint was actually a single board that had somehow been cut in half.
Using his knife blade, he pried the two sections from the floor and immediately discovered that several adjacent boards had been cut in an identical manner. By the time he’d removed all the loosened pieces, there was a substantial hole in the floor. Fetching a candle, Allen peered down into the cavity, and—to his astonishment—discovered that Jesse had actually managed to cut through a joist that ran beneath the floorboards and remove a half-dozen bricks from the outer wall of the cell by chipping away the mortar.
Interrogated by Warden Bridges, Jesse freely—even proudly—revealed the details of his latest scheme. For more than six months, he had “worked like a mole.” Every night, he would remove the loosened boards, and—reaching one arm down into the hole—peck away at the joist with an awl he had fashioned from a stout piece of wire pried from the rim of his water pail. Laboring with what the Globe described as “almost inconceivable patience,” he had finally managed to remove a section of the joist, then excavate the bricks until he had made a ten-by-twelve-inch opening in the outer wall. “To get through,” reported the Globe, “was only a question of time. Had he been allowed to dig for 24 inches further, he would have breathed the air of . . . freedom.”
The discovery of this audacious plan created an uproar. The night guard in charge of “Cherry Hill” was immediately suspended by the outraged warden, who told reporters that “he did not see how a convict could have worked for so many months without being detected. The boring and the scratching ought to have been easily heard.” Jesse himself, Bridges declared, had been treated with entirely too much leniency. He had been shown “every consideration” by his keepers and displayed nothing but “traits of ingratitude”
in return.
“Hereafter,” the warden vowed, “he will be placed under the closest surveillance, and his treatment will be of the most rigid sort.”
Still, no one seriously expected Pomeroy to abandon his desperate bids for freedom. As the Globe predicted, “It is safe to say that he will proceed to make another attempt as earnestly and with as great a will as he has in the past.”
In the following years, that prediction was fulfilled again and again. Shortly after midnight on Sunday, August 7, 1904, for example, a night officer named Charles Jorandorf heard a suspicious sound emanating from Pomeroy’s cell. Throwing open the door, he found Jesse crouched in a corner, chipping at the wall with a knife blade. Five years later, in October 1909, another officer, L. F. Burk—suspecting that Jesse was up to more mischief—summoned a colleague named Wood. As the two men entered Jesse’s cell, the startled prisoner popped something in his mouth and made for the toilet bowl. Before he could reach it, Burk and Wood wrestled him to the ground, forced his jaws apart, and extracted a small, chisel-shaped implement from his mouth. Another homemade tool turned up in August 1911, when an officer named Willard Davis—having reason to believe that Pomeroy was in possession of contraband material—frisked the prisoner and discovered a crude, eight-and-a-half-inch steel drill concealed inside his coat sleeve.
Except for the gas explosion episode of 1887, none of these escape attempts amounted to much. In 1912, however, Jesse actually managed to make it out of his cell.
It happened on the last day of the year. At around 2:30 A.M. on Monday, December 31, a guard named Thomas Brassil was patrolling the solitary wing. Aside from the usual sounds of sleeping men—a cough, snore, an occasional moan—there were no noises issuing from the cells. So eerily silent was the corridor that Brassil’s footsteps echoed audibly as he made his early-morning rounds.
A wooden armchair, used by the guards, stood at one end of the corridor. As Brassil passed it, he saw the prison mascot—a yellow cat named Buster—curled up on the seat. Brassil continued on his rounds. He was about to turn the corner and pass into the adjacent wing, when Buster—tail bristling, paws scrabbling on the concrete—came racing past him and vanished into the shadows ahead. Something had evidently startled the cat awake.
Puzzled, Brassil retraced his steps—then froze in surprise. Someone was crouched against the wall beside the chair. Though the man’s face was obscured by shadow, Brassil could see that he was dressed in the coarse garb of a convict. Drawing his revolver, the guard ordered the prisoner to “throw up his hands” and come out into the light. After a momentary pause, the man slowly rose to his feet, hands raised, and took a step forward. To his amazement, Brassil saw that it was Jesse Pomeroy. He immediately spotted something else, too—a large screwdriver clutched in Pomeroy’s right hand.
“Drop it,” Brassil barked, motioning his pistol at the implement. When Jesse hesitated, Brassil sprang forward, shoved the barrel of his gun into Pomeroy’s belly, and tried wresting the tool from his grasp. A brief tussle ensued, during which the guard sustained a few scratches on his left hand. In the end, however, he managed to secure the screwdriver. Then he marched Jesse into a holding cell and summoned the warden.
At first, Jesse sullenly refused to explain how he’d escaped from his seemingly impregnable cell. Eventually, however, the full story emerged. Using an improvised saw, he had managed to remove three bars from the bottom of his steel door. It had taken him three solid years of stealthy, nocturnal labor to get the job done. Worming his way through the hole, he had opened the outer wooden door by sticking his arm through the food slot and using the saw to work the iron bolt from its socket.
To fool any guard who peered into his cell, Jesse had resorted to the time-honored ruse of the prison escapee, creating a dummy out of an old carton and a bunch of newspapers, then arranging the bedclothes over it to make it appear as if he were sleeping peacefully on his cot.
His plan, once he broke out of his cell, was a little hazy. He apparently intended to sabotage the electric box controlling the lights in the solitary wing, plunging “Cherry Hill” into utter darkness and permitting him to escape in the confusion. In any event, his plan had come to nothing—thanks largely (as the newspapers told it) to the heroic vigilance of Buster, who gained instant celebrity as “The Cat Who Foiled Jesse Pomeroy.”
Following this latest failure, Jesse seemed genuinely deflated. He told Warden Bridges that he “had given up the idea of making any more attempts to escape,” and vowed to become “a model prisoner.” Besides, Jesse added, even if he did get out of prison,” he “would not know what to do or where to go.” He had known freedom for only thirteen years of his life. And on December 31, 1912—the day Buster the cat became a local hero—Jesse Pomeroy had just turned fifty-two.
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The great state which gave the lyceum its birth and its first real purpose, the state which wept over the sins of black slavery in the South, the state which morally gagged every time the word “bondage” was mentioned, has for forty years maintained a worse form of slavery than ever existed in South Carolina.
—Fred High, Prison Problems
On June 28, 1914—just a few months before the thirty-eighth anniversary of Jesse’s incarceration in Charlestown—a bullet fired by a young Serbian nationalist set off a conflagration that would engulf the world and create unimaginable desolation and suffering. From all available evidence, however, it appears that the start of the Great War made little or no impact on Jesse’s awareness. Not one of the many letters he wrote during the following year contains even a single reference to it. For him, the world was a nine-by-sixteen-foot cell, and the only suffering that mattered was his own.
Though he stuck to his pledge to forego any further escape attempts, he continued to churn out a steady stream of petitions, appeals, and complaints. On September 5, 1914, for example, he sent a letter to Frank L. Randall, chairman of the Massacusetts Prison Commission. As a mere boy of fourteen, Jesse wrote, he had been condemned to a sentence of “unmeasured inhumanity—‘Solitary imprisonment at hard labor for life’—and in these almost 40 yrs. since, nothing has been done to uplift this life, to hold before me any incentive, inducement, or privilege which might tend to bring me upon the road of reformation, to be a law-abiding citizen. I have been left to my own devices, and you will not find another 14 yr. old boy in that condition.”
Far from seeking to rehabilitate him, Jesse charged, the state had engaged in an active campaign to demonize him as a way of justifying the “unheard-of sentence.” “If half the effort which is made to distort the truth about me should be made to do something in my behalf,” he averred, “a great change and improvement would follow.” Urging the chairman to help him “in my effort to be something more than a degenerate (which I am not),” Jesse concluded by praying that “there may be for this friendless prisoner something beyond perpetual hard labor in solitary, pointing out that there are limits to human endurance, even if I have been outside the pale of human sympathy to this date.”
In point of fact, Jesse was not completely “beyond the pale of human sympathy.” By 1914, his situation had attracted the attention of various individuals, who agreed that—by condemning him to a lifetime in solitary—the Commonwealth of Massachusetts had committed an act of “unmeasured inhumanity.”
Besides his mother, Jesse’s most ardent supporter was a Chicago man named Fred High, publisher of a magazine called The Platform. In 1913, High brought out a volume called Prison Problems, an anthology of essays and poems whose high-minded purpose, as expressed in its preface, was to rouse public sentiment against the “barbarism of the present penal system . . . so that our penitentiaries shall cease to be criminal factories and become reform institutions.” High saw himself as a stalwart Christian reformer, one of the “soldiers of the common good” who were doing “our little mite towards bringing about a better day . . . for our fellows who have stumbled on the rough journey and have stepped aside from the straight and na
rrow path.”
As it happened, he was also a deep-dyed bigot and anti-Semite. In an April 1914 letter to the chairman of the Massacusetts Prison Commission, High compared Pomeroy’s situation to that of Leo Frank—the Jewish factory superintendent wrongfully accused of the murder of a thirteen-year-old girl named Mary Phagan in Atlanta, Georgia, in 1913. Frank’s conviction was widely denounced as a flagrant case of homegrown anti-Semitism—“the American counterpart of the Dreyfus affair” (as the Baltimore Sun put it). To High, however, Frank’s defenders were nothing but a “great army of Jews trying to save the neck of a Jew.” By contrast, he insisted, poor, friendless Jesse Pomeroy remained locked up in prison simply because he “does not happen to be Jewish, Irish, Geman, or any other nation that sticks up for their own.”
High’s most impassioned defense of Pomeroy appeared in the volume Prison Problems. The essay (the only one in the anthology written by High himself) begins with a bitter denunciation of the state of Massachusetts and, more specifically, of the Charlestown penitentiary. “The New Orleans slave market which stirred the soul of Abraham Lincoln to righteous wrath,” wrote High, “was an altar of justice as compared to the den of gloom where this human being, made in the image of his Creator, has been confined for forty long years. To me, Simon Legree was a merciful benefactor as compared to Warden Russell, who for twenty-one years has carried out the blind verdict of a jury, perhaps long since dead.”
The crux of High’s argument was that there was no defensible reason for subjecting Pomeroy to such punishment. “There are only two conclusions that a thinking mind can arrive at,” High declared. “First, this man, Jesse Pomeroy, is a degenerate, unsound of reason, with defective mental and moral faculties. If this is true, he should have had medical treatment, he should have been in a hospital, had fresh air, God’s sunshine, a mother’s love in more constant potions. . . . Shame on the state! Thrice shame on the officials if Jesse Pomeroy is as described!”
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