Remarkable Prison Escapes

by Allan Pinkerton

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I am certain that my readers will be interested in the recital of a few instances within my recollection where criminals, either convicts or prisoners awaiting trial for general offenses, have escaped their prison confines in a most ingenious and dramatic manner.  

 

On July 8, 1878, the city of Columbus, Ohio, was startled by a report that some forty prisoners, confined at the State penitentiary there, had escaped, and were “making a lively trial for tall timber” in all directions. A visit to the penitentiary proved that the reports were greatly magnified. Only three prisoners had escaped, but these had shown an amount of enterprise in getting outside of the walls that was truly remarkable.  

 

It was found, too, that even the three did not make their escape together, but that one had got out the previous night. He had been recaptured, and was once more a prisoner, although the other two were still at liberty. The one that had been recaptured had occupied a cell in one of the tiers of cell-houses on which the State was then placing a new roof. He managed, in some way, to dig out of his cell and gain access to the roof. A large derrick for elevating stone, used in the walls during the day, stood against the prison, but at night was pulled back quite a distance from it. The prisoner stood on top of the wall, and, calculating the distance in the darkness, made a leap, the like of which has never been attempted by any acrobat on earth, and, after descending at least thirty feet through the air, caught the derrick-rope and slid down the remaining distance, making his escape unobserved.  

 

What nerve and actual bravery were required for this! The convict risked his life more surely than if taking his chances in battle. The slightest miscalculation, the merest mischance, the least failure in estimating his power for leaping, would have caused him to have fallen a mangled corpse upon the stones below.  

 

But all this daring brought no reward to the poor fellow, for he was captured on the Pan Handle Road, near Summit Station, not ten hours subsequent to his marvelous escape.  

 

The other men did not show as much daring in their escape, but even more shrewdness and ingenuity. They were engaged cutting stone just north of the penitentiary. Through the aid of friends they supplied themselves with citizens’ clothing, which they secreted in a closet near where they were working, and leaped from this into a sewer leading into the Scioto River. As soon as they reached the bank, they stripped off their prison garb, and, donning their citizens’ clothing, strolled leisurely away. For all that is known, they are still leisurely strolling, as they have never been recaptured.  

 

One of the most desperate prison escapes ever known was made from Sing Sing prison on the morning of May 14, 1875, and would have ended disastrously to more than a score of lives had it not been for the presence of mind of Dennis Cassin, a Hudson River Railroad engineer.  

 

Just north of Sing Sing prison, between the extreme northern guard-house and the arched railway bridge, as you go south, is located the prison quarry, on the east side of the railroad track. From it, over the railroad track, on the west side, extends a bridge over which stone from the quarry is trundled in wheelbarrows by the convicts.  

 

At about eight o’clock, on the morning mentioned, an extra freight train, bound south, slowly approached the prison bridge. The train was drawn by “No. 89,” Dennis Cassin, engineer. They were slowly following the regular passenger train from Sing Sing to New York, which had left a few moments before. As the engine reached the trestle, or prison bridge, five convicts suddenly dropped upon it, from the bridge above; they were led by the notorious “Steve” Boyle and Charles Woods.  

 

Four of them ran into the engineer’s cab, while the other hastened to the coupling which attached the train to the engine. The convicts on the cab, with drawn revolvers, ordered the engineer and fireman to jump off, which they did, when the convicts put on steam, and the engine started down the road at lightning speed.  

 

Their escape was detected almost immediately, and several shots were fired after them by the prison-guard, but without effect. Then began the pursuit. The superintendent of the railroad was notified quickly, when a telegraph alarm was sounded at all points south of Sing Sing. A dispatch was sent to the Tarrytown agent directing him to turn the switch at that station on the river side, so as to let the engine, with the convicts on board, jump the bank and plunge into the river. Danger signals were also ordered to be set on the down track, and prompt measures of every kind were taken to prevent danger from collision with the stolen locomotive. The trackmen in the vicinity of Scarborough saw the engine coining like lightning, or rather saw a vast cloud of smoke and steam and water, whirl by with a deafening roar, and gazed with terror at the frightful speed the engine had attained. At Tarrytown crowds of people were gathered, expecting to see the engine dash into the station, and off the switch into the river; but it did not arrive.  

 

After waiting a short time, the Tarrytown agent sent an engine cautiously up the road to look for the stolen property; and “No. 89” was finally found, with both cylinder-heads broken, three miles north and opposite the “Aspinwall Place.” The boiler was full of water and the steam down. The convicts had left the disabled engine a half mile further north, and had disappeared into the dense Aspinwall woods, having first stolen all the clothing which could be found in the engineer’s and fireman’s boxes in the tender.  

 

Engineer Cassin’s wonderful presence of mind undoubtedly prevented a large destruction of property and human life. He was surrounded by the four convicts before being conscious of it, and could feel the cold muzzles of their revolvers against his head. Instantly after he realized what had occurred.  

 

“Get off! get off!” the desperate men shouted. They did get off, and that right lively; but Cassin did not turn from his place until he had prevented disaster. Just before the convicts jumped into the cab, he had three gauges of water in the boiler, and had shut off the pumps; but, as he turned to go when ordered, he shoved the pumps full on, the convicts not noticing the movement. The desperadoes undoubtedly pulled the throttle-valve wide open when they started, and for a little time the engine attained a terrific speed; but finally the cylinders got so full that both heads were blown out, or broken, and that necessarily ended the trip.  

 

None of the daring fellows were immediately recaptured, but the eventual return of the leader of the escapade was effected through my office; and how it all came about necessitates a short sketch of “Steve” Boyle, the leading and most desperate spirit in the escape just narrated.  

 

Boyle is a noted “houseworker,” or house-burglar, and general thief, and has nearly always been brilliant and successful in whatever he has undertaken. His work was principally done in the East, until 1867, when that part of the country became too warm for him, and, in company with his “gang,” consisting of “Bob” Taylor, “Torn” Fitzgerald, alias “Big Fitz,” and William —, alias “Black Bill,” he removed to Chicago.  

 

Their first operation in that city was very unfortunate for Boyle. They were “working” a residence in the West Division, and Boyle was “doing” the rooms and passing the plunder out to his confederates, when, being very weak from a severe attack of the asthma, he made a misstep, stumbled, dropped his revolver, and caused such a noise that in an instant the gentleman of the house was upon him with a cocked revolver in his hand, and effected his capture easily.  

 

As he was then comparatively unknown in the West, on the plea of ill-health, first offense, respectable parents, and the like, he succeeded in escaping with a sentence of but one year’s imprisonment at Joliet, Illinois.  

 

His comrades now employed every effort in their power to secure a pardon for Boyle, using large sums of money for this purpose; but this failing, they eventually found a way of conveying money to him within the penitentiary. Whether or not this was more powerful than whatever instruments to effect his escape Boyle may have secured, I cannot say; but, at all events, a plan of escape was determined on, which proved successful; and, on a certain night, Boyle, at the head of eleven other convicts, made their way from the cells up into one of the guard towers used for the sentry, and thence, in some mysterious manner, which has never since been fully explained, not only made good their escape, but carried away all the arms—quite a number—which were stored in the tower.  

 

Boyle’s hard luck seemed about equal to his good fortune and ability to conquer difficulties.  

 

The second day after escaping from the Illinois penitentiary, as he needed money, himself and another of the escaped prisoners were arrested in Chicago while in the act of “tapping” the till of a North Side German grocery. They were locked up for the night together at one of the North Side stations. Boyle’s companion was possessed of a terrible fear that he would be recognized and returned to Joliet.  

 

“Oh, I’ll fix all that!” said Boyle jauntily; and forthwith he set to work and gave his ex-convict comrade such a pummeling, disfiguring his face and blacking his eyes, that his own mother would not have recognized him.  

 

The next morning they were put in charge of separate policemen, who started with their prisoners for the police court on the South Side. The officer in charge of Boyle was a huge German, weighing fully two hundred and twenty-five pounds. When the two had arrived at a point on North Wells Street, near the river, Boyle’s keen eyes discovered a house of disreputable character, which he had formerly frequented. A negress, a servant at the establishment, was scrubbing the steps in the early morning before the inmates had arisen, and the basement-door stood wide open. As quick as thought, Boyle planted a terrific blow squarely in the big Dutch policeman’s belly, doubling him up like a stage harlequin going backward through a trap, and then, leaping over and beyond the horrified black woman at one bound, darted into the house, and shut and bolted the door behind him. Then he sped through the basement to the rear of the house and escaped. His companion, who had been herded in the “bull-pen” along with the regular daily collection of petty offenders, was finally brought before the police justice, and the grocery-man whose till had been robbed failing to identify him, he was fined five dollars, as a simple case of “drunk,” on general principles. The fine was paid by some of his friends, who had learned of his predicament, and thus he too escaped.  

 

About this time the other portion of Boyle’s gang had endeavored to rob a bank at Schoolcraft, Michigan. They had succeeded in getting into the vault, and had already got open the outer door to a large safe standing within it, when a sleigh-riding party, out on a lark, came dashing up to a point near the bank, shouting and hallooing in a boisterous and roystering fashion. The thieves, thinking they had been discovered, fled from the place, leaving their tools and their nearly secured booty behind them.  

 

From here they went to Kalamazoo, Michigan, and, securing new tools from Chicago, made an attempt to rob a bank there, but were all arrested, and, being recognized as the parties engaged in the unsuccessful Schoolcraft job were held without bail.  

 

Through a friend in Kalamazoo who was then closely allied with rogues of this class, but who is now a respected citizen of that city, word of their misfortune was conveyed to Boyle in Chicago, who, with a New York thief named Harry Darrah, returned the cheering intelligence that they would be over to Kalamazoo on a certain night, and give them “a break,” that is, liberate them.  

 

On the night in question, true to their word, Boyle and Darrah got so far toward the liberation of their friends as to have passed pistols and small steel saws in to them in the jail, when Colonel Orcutt, the sheriff, whose apartments were in the jail building, discovered the efforts being made, and, coming upon the scene en dishabille, with cocked revolver in hand, endeavored to arrest the jail-breakers.  

 

The men instantly fled, Colonel Orcutt pursuing. He ordered them to halt, but they did not comply; and he began firing upon them, succeeding in shooting Darrah’s hat from his head. This only had the effect to increase his efforts to escape. Boyle, whose chronic asthma made it impossible for him to run any distance, suddenly dodged behind a tree, unperceived by the sheriff, and, when the latter passed him in hot pursuit of Darrah, the cowardly ruffian Boyle fired upon him, shooting him through the spine, and effecting a wound from which Colonel Orcutt died twelve hours after. Darrah skulked about the place for a few days, and finally disappeared, while Boyle, on the same night, secreted himself upon an eastern-bound freight-train, went to Detroit, and from thence into Canada, where, after remaining under cover for a few weeks, he proceeded to New York, being soon after rejoined by Darrah, who was subsequently arrested for pocket-picking, and, being identified, was returned to Kalamazoo, where he made a full confession, implicating Boyle in the murder of Colonel Orcutt.  

 

He eluded arrest, however, for nearly a year, when, his bad fortune following him, he was captured in New York while attempting to do what is known as the “butcher cart job.” This is effected in the following manner:  

 

At a time of the year when street doors of jeweler shops are usually closed throughout the day as well as the evening, a common grocer’s, or delivery wagon of any sort, but always selected for its easy-running qualities, and to which is always attached a fast horse, will be driven up to the vicinity of some jewelry-store, which has already been fixed upon, and which always has a fine display in the window This wagon will invariably contain one, and sometimes two persons, aside from the driver. In the meantime a confederate of this “butcher-cart gang” slips up to the door of the shop in question, and deftly inserts a wooden peg or wedge beneath the door, between that and the sill, driving it home with his heel or in any other manner possible. The moment this is done another of the gang at one stroke smashes in the entire window, and the two then grab whatever they can lay their hands upon, always of course selecting that which is the most valuable, and rush to the covered wagon in waiting, when, with their booty, they are driven rapidly away, nine times out of ten getting wholly beyond pursuit before the astonished and shut-in shopmen are able to get their own door open.  

 

It was while Boyle was conducting an operation of this kind that he was captured, and, rather than be conveyed to Michigan, to answer the charge of murder, he made no defense, but pleaded guilty to everything brought against him, and was finally sentenced to twenty years’ imprisonment at Sing Sing.  

 

It was the boast of himself and his friends that no prison had been built strong enough to hold him, arid a special guard was for a time placed over him.  

 

Illustrative of the man’s cunning is the fact that, one day, while being so watched, he slipped his jacket and hat upon a broom standing near, and then, noiselessly placing it where he had sat, stole away from his guard entirely. It was some minutes before the watchful guard discovered the trick which had been played upon him, and Boyle had made so good a use of his time that eight hours had elapsed before he was found. He had secreted himself in the prison, with the hope of escaping the same night.  

 

The next instance in Boyle’s career worthy of note was the planning and execution of the desperate escape from Sing Sing upon the engine “No. 89,” as has been related.  

 

In company with Charles Woods, one of the convicts escaping with him on that occasion, Boyle then secured a “kit” of burglar’s tools, and the two proceeded to St. Louis, where they began operating upon small safes in real estate and brokers’ offices. They deposited their tools in what they believed to be a deserted carpenter’s shop. The proprietors, returning unexpectedly, discovered the tools, and, informing the police, a detail of officers was at once made to lie in wait for the owners of the suspicious goods, who returned, and, before being given time to explain anything, were unmercifully clubbed and taken into custody.  

 

The men being utter strangers to the St. Louis authorities, were only given six months in the workhouse. Their pictures were taken, however, and, a set coming into my office, that of Boyle was recognized, when, on his being fully identified by my son, William A. Pinkerton, he was returned to Sing Sing, where, fortunately for society in general, he is now serving his unexpired term of twenty years’ imprisonment.  

 

In 1870 George White, alias George Miles, alias George Bliss, made one of the most remarkably brilliant prison escapes on record.  

 

He had, in company with one Joe Howard, another bank burglar, robbed the bank of an interior New York town, and, securing a noted race-horse of the locality in escaping from the place, ran the animal nearly thirty miles at its fullest speed, until it fell to the earth from sheer exhaustion. The men then brutally cut the throat of the horse, leaving it dying. The men were subsequently captured, convicted, and incarcerated in Sing Sing. While here, White made the acquaintance and friendship of a noted character, named Cramer, familiarly called Doctor Dyonissius Cramer, or “the Long Doctor,”now a reformed thief, but in his day one of the cleverest known “stalls” of the “bank sneak gangs.” This “Long Doctor” had a peculiarly inventive genius, and I am happy to say that now, as he has become an honest man, it is securing for him considerable wealth.  

 

His familiarity with White resulted in his inventing—more as a curious experiment than anything else—a hollow rubber apparatus, which, when completed, had the exact appearance of a very large decoy duck. This was also provided with rubber tubes for breathing through; and one morning, when a party of convicts were working along the docks by the side of the river, White, who had secreted the contrivance in his clothing, at an opportune moment adjusted it, and, slipping into the water, calmly floated down the Hudson, passing within twenty feet of the guards, thus making his escape.  

 

His recapture would have been certain, but Colonel Whitley, then Chief of the Secret Service, made such strong representations to the Government authorities that his use by the Government in ferreting out several important counterfeiting cases would be valuable, that he eventually secured for him from the Governor of New York a free pardon. The value of his subsequent services may be inferred when it is stated that Colonel Whitley used him as one of the chief actors in the infamous sham robbery of the safe of the district attorney’s office in Washington, when it was sought to ruin the Hon. Columbus Alexander, who was nobly fighting the Washington ring and its corruptions.