This story is over 5 years old.

The True Crime Issue

The Hows and Whys of Prison Escapes

Famed crime writer Donald E. Westlake on history's most famous jailbreaks.

All illustrations by Joseph Remnant

Over the course of his 50-year career, Donald E. Westlake wrote more than 100 books, the vast majority of them crime fiction—most often seen from the point of view of the criminals. In 1993, the Mystery Writers of America gave him their highest honor, naming him Grand Master, largely on the strength of his two classic series: one featuring hard-boiled burglar Parker (played on screen by Lee Marvin, Robert Duvall, Mel Gibson, and Jason Statham, among others), the other portraying hapless heister John Dortmunder (who lucked out and got Robert Redford—go figure).


Along the way, Westlake wrote a fair amount of nonfiction, usually relating in some way to the crime genre. In October, the University of Chicago Press will publish a selection of that nonfiction in The Getaway Car: A Donald E. Westlake Nonfiction Miscellany. The piece below, an essay originally published in 1961 in the third issue of Ed McBain’s Mystery Book, is a selected history of the hows and whys of great prison breaks. As a writer, Westlake always enjoyed putting his characters into agonizingly difficult situations and seeing how they get out; that enthusiasm for an impossible puzzle animates this essay.

Alcatraz is probably the toughest and best-known prison in the United States, long considered an impregnable, escape-proof penitentiary. The entire imprisoned population there consists of hard cases transferred from less rugged federal penitentiaries. In the middle of San Francisco Bay, it is surrounded by treacherous currents and is almost always enveloped by thick fog and high winds. A high percentage of the prisoners sent there are men who have already escaped from one or more other prisons and penitentiaries. “Now you are at Alcatraz,” they are told. “Alcatraz is escape-proof. You can’t get away from here.”

It was a challenge, and sooner or later someone had to accept it. That someone was a felon named Ted Cole. Cole had already escaped once, from an Oklahoma prison, where he had been assigned duty in the prison laundry. That escape had been made by hiding in a laundry bag. But now Cole was on Alcatraz, and Alcatraz, he was told repeatedly, was escape-proof.


Cole’s work assignment was in the prison machine shop, which suited him perfectly. Through an involved code in his infrequent mail, he managed to line up outside assistance from friends in the San Francisco area. While waiting for things to be set up outside, he spent a cautious part of each workday on the machine-shop wall, on the other side of which was the rocky, surf-torn beach of the island.

The day finally came. Leaving right after a head count, so he would have an hour or two before his absence was noticed, Cole went through the machine-shop wall and dove into the water, swimming straight out from the island, the fog so thick around him he could barely see the movement of his own arms as he swam.

This, as far as he was concerned, was the only really dangerous part of the escape. If his friends couldn’t find him in the fog, he would simply swim until he drowned from exhaustion or was recaptured by a police patrol from the island.

Finally, a launch came out of the fog ahead, throttling down beside him, and Cole treaded water, staring anxiously, wondering whether this was escape or capture.

It was escape. His friends fished him out of the water, gave him blankets and brandy, and the launch veered away toward shore. Yet again, society’s challenge had been accepted, and another “escape-proof” prison had been conquered.

Accepting society’s challenge in his own antisocial way is second nature to the habitual criminal. The desire for freedom is strong in most men, and perhaps it is strongest in those who have, by the commission of crime, tried to free themselves from the restraint of society’s laws. The much harsher and much more complete restraint of a narrow prison cell and an ordered, repetitive existence within the prison walls, plus the challenge of being told that escape from this prison is impossible, increase this yearning for freedom to the point where no risk seems too great, if only there is the possibility of freedom. No matter what the builders of the prison have claimed, the imaginative and determined prisoner can always find somewhere, in a piece of wood or a rusty nail or the manner of the guards’ shift change, the slim possibility that just might end in freedom.


This yearning for freedom, of course, doesn’t always result in imaginative and ingenious escapes. At times, it prompts instead wholesale riots, with hostages taken and fierce demands expressed and the senseless destruction of both lives and property. Such outbreaks are dreaded by prison officials, but they never result in successful escapes. They are too noisy and too emotional. The successful escapee is silent, and he uses his wits rather than his emotions.

The prisoner who is carefully working out the details of an escape, in fact, dreads the idea of a riot as much as do the prison officials themselves.

The result of a riot is inevitably a complete search and shakedown of the entire prison. And this means the discovery of the potential escapee’s tunnel or hacksaw or dummy pistol or specially constructed packing case or rope ladder or forged credentials. And the escapee has to think of some other plan.

He always does. No matter how tight the control, how rigid the security, how frequent the inspections or “impregnable” the prison, the man who desires freedom above all other things always does think of something else.

Take John Carroll, perhaps the only man ever to break both out of and into prison. In the 20s, Carroll and his wife, Mabel, were known throughout the Midwest as the Millionaire Bandits. Eventually captured and convicted, John Carroll was sentenced to Leavenworth while Mabel was imprisoned at the women’s reformatory at Leeds.


At that time, in 1927, Leavenworth was still thought of as being nearly escape-proof, and the constant shakedowns and absolutely rigid daily schedule had Carroll stymied for a while. But not forever.

Carroll had been put to work in the machine shop, and he spent months studying the guards, realizing that he would be much more likely to escape if he could get one of them to collaborate with him.

He finally picked the shop foreman himself, a truculent, middle-aged, dissatisfied guard obviously unhappy in his work. Carroll waited in the machine shop one afternoon until everyone else had left and he was alone with the foreman. The foreman wanted to know what he was still doing here. Carroll, making the big leap all at once, said, “How would you like to make thirty-four thousand dollars?”

The foreman showed neither interest nor shock. Instead, he demanded, as though it were a challenge, “How do I do that?”

“I have sixty-eight thousand hidden on the outside,” Carroll told him. “Help me get out of here, and half of it is yours.”

The foreman shook his head and told Carroll to go on with the others. But the next day, when work was finished, he signaled to Carroll to stay behind again. This time, he wanted to know what Carroll’s plans were.

Carroll told him. A part of the work in this shop was devoted to building the packing cases in which the convict-made goods were shipped outside. Carroll and the foreman would construct a special case, and when Carroll felt the time was right, the foreman would help him ship himself out of prison and to the foreman’s apartment.


The foreman agreed, and they went to work. Carroll was a cautious man, and they worked slowly, nor did Carroll make his escape immediately after the special packing case was completed. Instead, he waited for just the right moment.

A note from his wife, delivered through the prison grapevine, forced Carroll to rush his plans. The note, which he received on February 28, 1927, read: “Your moll has t.b. bad. I’ll die if you don’t get me out. I’m in Dormitory D at Leeds.”

Carroll knew that his wife’s greatest terror was of dying in prison, of not dying a free woman. He left Leavenworth that same night, in the packing case. But the case was inadvertently put in the truck upside down, and Carroll spent over an hour in that position, and had fallen unconscious by the time the case was delivered to the foreman’s apartment.

Coming to, Carroll broke out of the case and discovered the apartment empty and the new clothes he had asked for waiting for him on a chair. He changed and left before the foreman got home, and the foreman never saw a penny of the $34,000.

Carroll went straight to Leeds. Posing as an engineer, he became friendly with one of the matrons from the prison, and eventually learned not only the location of Dormitory D within the wall but even the exact whereabouts of his wife’s cell.

It took him five months to get his plan completely worked out. Finally, shortly after dark the night of July 27, he drove up to the high outer wall of the prison in a secondhand car he’d recently bought. In the car were a ladder, a hacksaw, a length of rope, a bar of naphtha soap, and a can of cayenne paper.


Setting the ladder in place, Carroll climbed atop the wall and lay flat, so as not to offer any watchers a clear silhouette. He then shifted the ladder to the other side of the wall, climbed down into the prison yard, and moved quickly across to Dormitory D. He stood against the dormitory wall and whistled a shrill, high note, a signal he knew his wife would recognize. When she answered, from her barred third-story window, he tossed the rope to her. She caught it on the third try, tied one end inside the cell, and Carroll climbed up to the window.

Mabel then spoke the only words either of them said before the escape was complete. “I knew you’d come.”

Carroll handed the tools through to his wife, then, one-handed, tied the rope around his waist, so he’d have both hands free to work. Meanwhile, Mabel had rubbed the hacksaw with soap, to cut down the noise of sawing. They each held an end of the saw and cut through the bars one by one, with frequent rest stops for Carroll to ease the pressure of the rope around his waist.

It was nearly dawn before they had removed the last bar. Carroll helped his wife clamber through the window, and they slid down to the ground, where Carroll covered their trail to the outer wall with cayenne powder, to keep bloodhounds from catching their scent. They went up the ladder and over the wall and drove away.

Carroll was recaptured over a year later, and returned willingly enough to jail. His wife was dead, had been for five months. But she hadn’t died in prison.


Most escapees don’t remain on the outside for anywhere near as long as a year. The majority seem to use up all their ingenuity in the process of getting out, and none at all in the job of staying out. Such men have fantastic courage and daring in the planning and execution of one swiftly completed job, be it a murder or a bank robbery or a prison break, but seem totally incapable of giving the same thought and interest to the day-to-day job of living successfully within society.

Another escape from Leavenworth is a case in point. This escape involved five men, led by a felon named Murdock. Murdock, employed in the prison woodworking shop, was a skilled wood-carver and an observant and imaginative man. On smoke breaks in the prison yard, Murdock had noticed the routine of the main gate. There were two gates, and theoretically they were never open at the same time. When someone was leaving the prison, the inner gate was opened, and the outer gate wasn’t supposed to be opened until that inner gate was closed again. But the guards operating the gates had been employed in that job too long, with never a hint of an attempted escape. As a result, Murdock noticed that the button opening the outer gate was often pushed before the inner gate was completely closed, and that once the button was pushed, the gate had to open completely before it could be closed again.

This one fact, plus his wood-carving abilities, was the nucleus of Murdock’s escape plan. He discussed his plans with four other convicts, convinced them that it was workable, and they decided to go ahead with it. Murdock, working slowly and cautiously, managed to hide five small pieces of wood in the shop where he worked. Taking months over the job, he carved these pieces of wood into exact replicas of .38-caliber pistols, down to the safety catch and the trigger guard, then distributed them among his confederates.


The day and the time finally came. A delivery truck was leaving the prison while Murdock and the other four were with a group of prisoners on a smoke break in the yard. Murdock saw the outer gate opening before the inner gate was completely closed. He shouted out the prearranged word signal and ran for the gate, the other four with him. They squeezed through just before the inner gate closed all the way, and Murdock, brandishing his dummy pistol, warned the guards not to reopen it. The five dashed through the open outer gate and scattered.

This much planning and imagination they had given to the job of getting out. How much planning and imagination did they give to the job of staying out? Murdock himself, the ringleader, was the first one captured, less than 24 hours later. He was found, shivering and miserable, standing waist-deep in water in a culvert. A second was found the following morning, cowering in a barn, and numbers three and four were rounded up before the week was out.

The fifth? He was the exception. It took the authorities nearly 20 years to find him, and when they did, they discovered he had become the mayor of a small town in Canada. His record since his escape from Leavenworth was spotless, and so he was left to live out his new life in peace.


The courage and daring, the ingenuity and imagination, the skill and talent demonstrated in these and similar escapes, if used in the interests of society rather than directed against society, would undoubtedly make such men as these among society’s most valuable citizens. But the challenge is given these men, and they accept that challenge. They are not challenged to use their talents to benefit society, but to outwit society.


In fact, there seems to be a correlation between rigidity of control and attempts to escape. The tighter the control, the stronger and more secure and solid the prison, the more escape plans there will be, the more attempted escapes, and the more successful escapes.

The career of Jack Sheppard, probably the most famous despoiler of “escape-proof” prisons of all time, is a clear-cut demonstration of this. In one five-month period in 1724, Sheppard escaped from Newgate, England’s “impregnable” prison, no less than three times! The first time, he had help from inside the prison, which is probably the easiest and most common type of jailbreak. The second time, he had tools and assistance from outside, a little more difficult but obviously not impossible. The third time, without tools and absolutely unaided, he successfully completed one of the most daring and complex escapes in history.

Sheppard, born in 1701 and wanted as a highwayman and murderer before he was out of his teens, was first jailed in Newgate in May of 1724. When arrested, he had been with a girlfriend, Bess Lion, who was also wanted by the police. They swore they were married and so, in the manner of that perhaps freer day, they were locked together in the same cell. Bess had managed to smuggle a hacksaw in with her—history doesn’t record how—and as soon as the two were alone, they attacked the bars of the window. But it was a 25-foot drop to the prison yard, and the rope ladder they made of their blankets didn’t reach far enough. So Bess removed her clothes, which were added to the ladder, and they made their way down to the yard, nude girl first. Bess rolled her clothes into a bundle, and she and Sheppard climbed over a side gate which was no longer in use. Bess put her clothes back on, and the two of them walked away.


He was recaptured almost immediately, returned to Newgate, and this time held long enough to be tried for his crimes and sentenced to be hanged. The day before the scheduled hanging, he was brought, chained and manacled, to the visitors’ cell. His visitors were Bess and another girlfriend, Poll Maggott. While Bess “distracted” the guard—history is somewhat vague on this point, too—Poll and Sheppard sawed through the bars separating them, and Poll, described as a “large” woman, picked Sheppard up and carried him bodily out of the prison since the ankle chains made it difficult for him to walk.

That was July of 1724. Two months later, Sheppard was captured for the third time and once more found himself in Newgate. This time, the authorities were determined not to let him escape. He was allowed no visitors. After a whole kit of escape tools was found hidden in his cell, he was moved to a special room known as the Castle. This room was windowless, in the middle of the prison, and with a securely locked double door. There was no furniture, nothing but a single blanket. Sheppard’s wrists were manacled, and his ankles chained, with the ankle chain slipped through an iron bold embedded in the floor.

Sheppard, at this time, was 23 years of age. He was short, weak, sickly, suffering from both a venereal disease and too steady a diet of alcohol. His physical condition, plus the manacles and the placement of his cell, seemed to make escape absolutely impossible.


Sheppard waited until October 14, when the opening of Sessions Court was guaranteed to keep the prison staff too busy to be thinking about a prisoner as securely confined as himself. On that morning, he made his move.

First, he grasped in his teeth the chain linking the wrist manacles, squeezed and folded his hands to make them as small as possible, and finally succeeded in slipping them through the cuffs, removing some skin in the process. He then grabbed the ankle chain and with a single twisting jerk, managed to break the link holding him to the bolt in the floor.

He now had a tool, the one broken link. Wrapping the ankle chains around his legs to get them out of the way, he used the broken link to attack one wall, where a former fireplace had obviously been sealed up. He broke through to the fireplace, only to discover an iron bar, a yard long and an inch square, bisecting the flue a few feet up, making a space too small for him to slip by.

Undaunted, he made a second hole in the wall, at the point where he estimated the bar to be, found it and freed it, and now had two tools as well as an escape hatch. He crawled up the flue to the floor above, broke through another wall, and emerged into an empty cell. Finding a rusty nail on the floor—for tool number three—he picked the door lock with it, and found himself in a corridor. At the end of the corridor he came to a door bolted and hinged on the other side. He made a small hole in the wall beside the door, reached through and released the lock.


The third door, leading to the prisoners’ pen in the chapel, he popped open with the iron bar. The fourth door got the same treatment, and now he came to a flight of stairs leading upward. He knew his only chance for escape lay in reaching the roof.

This sixth door was fastened with a foot-wide iron-plated bar, attached to door and frame by thick iron hoops, plus a large iron bolt lock, plus a padlock, and the whole affair was crisscrossed with iron bars bolted to the oak on either side of the door.

Sheppard had now been four hours in the escape. He was exhausted, his hands were bleeding, the weight of the leg shackles was draining his energy, and the door in front of him was obviously impassable. Nevertheless, Sheppard went to work on it, succeeding at first only in bending the iron bar he was using for a tool.

It took him two hours, but he finally managed to rip the crossed bars down and snap the bolt lock, making it possible to remove the main bar, and he stepped out onto the prison roof.

So far, the escape had taken six hours. It was now almost sundown. Sheppard crossed the roof and saw the roof of a private house next door, 20 feet below him. He was afraid to risk the jump, not wanting to get this far only to lie down there with a broken ankle and wait for the prison officials to come drag him back. So, regretfully, he turned around, recrossed the roof, went down the stairs and through the chapel, back down the corridor and into the cell above the Castle, down the fireplace flue and back into his cell, which was ankle deep in stone and plaster from the crumbled wall. He picked up his blanket, retraced his steps again, and went back to the roof. He had forgotten tool number four, and so he had simply gone back for it!

Atop the prison again, Sheppard ripped the blanket into strips, made a rope ladder, and lowered himself to the roof of the house next door. He waited there until he was sure the occupants had gone to sleep for the night, then he crept down through the house and out to freedom.

In the ordinary manner of escapees, however, Sheppard could never learn to devote as much energy to staying out as to getting out. He spent the first four days hidden in a cowshed, until finally someone came along who would bring him a hacksaw and help him shed the ankle chains. He then went straight home, where he and his mother celebrated his escape by getting drunk together on brandy. They were still drunk when the authorities showed up, and this time Sheppard stayed in Newgate long enough to meet the hangman.


Here is the core of the problem. The tougher the prison officials made their prison—the more they challenged Sheppard and told him that this time he couldn’t escape—the more determined and daring and ingenious Sheppard became.

This misdirected genius was never more evident than in the ten-man escape from Walla Walla State Penitentiary in Washington State in 1955. Their escape route was a tunnel under the main wall, but one tunnel wasn’t enough for them. They also had tunnel routes between their cells, so they could communicate and pass materials and information back and forth. When they were recaptured—which, in the traditional manner, didn’t take very long at all—the full extent of their ingenuity and daring was discovered. Each of the ten carried a brief case containing a forged draft card, business cards, a driver’s license, birth certificate, and even credit cards and charge-account cards for stores in Seattle. Beyond all this, they all carried identification cards claiming them as officials of the Washington State prison system, and letters of recommendation from state officials, including the warden of the Walla Walla State Penitentiary. And four of the escapees carried forged state paychecks, in amounts totaling over a thousand dollars. Every bit of the work involved had been done in the prison shops.

Compare this with the record of a jail such as the so-called “model prison” at Chino, California. Escaping from Chino is almost incredibly easy. There is a fence, but no wall, and the fence would be no barrier to a man intent on getting away. The guards are few, the locks fewer, much of the prisoners’ work is done outdoors, and the surrounding area is mostly wooded hills. For a man determined to escape, Chino would offer no challenge at all.

And yet, Chino has had practically no escapes at all!

Perhaps the lack of challenge is itself the reason why there are so few escapes from Chino. The cage in which the prisoner must live is not an obvious cage at Chino. He is restricted, but the restrictions are subtle, and he is not surrounded by stone and iron reminders of his shackled condition. At tougher, more security-conscious prisons, the challenge is flung in the convict’s face. “You cannot escape from here!” Inevitably there are those who accept the challenge.

The challenge at Chino—and at other prisons constructed from much the same philosophy—is far different. “You should not escape from here! And when you know why society demands that you stay here, you won’t need to escape. You will be released.”

Both challenges demand of the prisoner that he think, that he use his mind, his wit and his imagination. But whereas the one challenge encourages him to think along lines that will drive him yet further from society, the other challenge encourages him to think along lines that will adjust him to society.

No matter which challenge it is, there will always be men to accept it, as the warden of Walla Walla State Penitentiary—from which the ten convicts escaped with their forged-card-bulging brief cases—inadvertently proved, back in 1952. He gave the prisoners a special dinner one day in that year, in honor of the fact that a full year had gone by without the digging of a single tunnel. Three days later, during a normal shakedown, guards found a tunnel 100 feet long.