Detective Pinkerton


How He Captured a Mail Robber


The Hob-Nailed Boots, Etc.


[From the N.Y. Evening Post]

Many years ago, when Western railroad traveling was not the safest in the world, and when all the moneys due from the East in payment for Western produce had to be sent in cash by the mails, there occurred, not far from Chicago, each time several accidents in consequence of trains being thrown off the track, during which mail cars were broken open and the bags robbed to a very large amount. The first of these accidents happened within six miles of the “Garden City,” and was caused by the Michigan Southern running into the Illinois Central mail train, if I remember rightly, striking it at right angles, and not only cutting it into two parts, but making a complete wreck of both trains.

The loss in every way was large, and the conductor and engineer were killed on the spot—the former lying with his face upwards near the mail car—which it was afterward discovered had been forced open and the gold and silver it contained carried off. Mr. Pinkerton, the great western detective, who was then beginning one of the most remarkable and successful careers known to police history, was sent for to investigate the robbery, and he discovered on the face of the dead conductor of the train the imprint of a nail head, such as was usually worn by English laborers in the soles of their heavy boots. He then examined the ground, and was lucky enough to find a complete imprint of the sole of the left boot, containing a double row of nails, all of which were exactly like that on the conductor’s face. He made also another important discovery—that there were three nails wanting in the impress on the earth, showing that three were also wanting on the sole of the boot that made it.

Mr. Pinkerton’s theory so far was this—that the robber was in so great a hurry to force open the mail car that he set his left foot upon the face of the dead man without knowing it, and thinking no doubt that it rested on the earth; and that one of the nails—“hob-nails” he called them—having started from the leather, was more prominent than the rest, and so left its mark behind it, and with it a secret clue for the detective. Unfortunately, before Pinkerton came on the ground, there had been so many people about that the earth was trodden down hard in the neighborhood of the calamity, and he had no chance of tracing the hob-nailed boot and discovering its owner.

He had made some important discoveries, however, during this difficult investigation. He had found out that the robber, whoever he was, wore boots nailed with hob-nails in a peculiar form round the soles, with three nails missing; and that the boots were of English make, and the wearer of them, therefore, was probably an Englishman, and that the left boot had made an impression of the face of the dead conductor, and on the ground. This was all the clue he had to the robber; but meager as it was, he did not despair of hunting down his quarry. He did not believe, however, that the collision of the trains was purposely caused, but that it was an accident, and that the robbery was a sudden evil inspiration on the part of the robber.

Eighteen months passed away, and Pinkerton, although more or less on the watch, had well-nigh forgotten the hob-nailed boots, when one fine morning he received a telegraphic dispatch, which summoned him to another accident, which had just happened on the same railroad, within twelve miles of the city of Chicago. On his arrival, he found a great concourse of persons, officers and men and passengers, about the wreck, and he immediately ordered a rope to be payed out and guarded by the company’s servants, while he made an examination of the ground, and search for the hob-nailed boots, if, by any chance, they might figure upon this scene also. He first examined the locality where the obstruction was placed that overthrew the train, and, in his great joy and surprise, there was the old boot mark with the many hob-nails; and a full impression also of the right boot. Of course he said nothing, but began to make detours in all directions to see if he could pick up the retreating trail.

He thought it most likely the man would go boldly towards the village after he had laid his trap, and so he hastened on till he came to a bit of grass leading to the main road on the heights above. Here he stumbled upon the footmark once more, and proceeding right and left upon a line with this discovery, he found the advancing foot too. The grass, however, threw him off all further trail, but he had proved that the same man who had a hand in the robbery had planned the present disaster also; and better still, that he came from, and returned to the village. Owing to some accident elsewhere, this train was late by several hours. It was an early morning train, and the design clearly was to throw it off the lines and rob the mails, but it was defeated.

Mr. Pinkerton remained privately in the village, putting up at the chief hotel, and passing for a salesman of dry goods for several weeks, making observations and notes. He soon knew everybody in the place, and had not been there a week before he began to suspect a man who was then absent, but who, when in town, stopped at the hotel where he then lodged. A short time afterwards he returned, and Pinkerton found that he was an Englishman, and began to look for his cloven foot. But he did not wear it at the time he was introduced to him, and Pinkerton reasoned that such boots as those hob-nailed ones could only be in requisition in wet or dirty weather, and he began to pray that it might rain. He kept a severe and close watch upon the Englishman, and followed him always when he could do so without detection.

A fortnight passed away, and the Englishman began to exhibit signs of great uneasiness and unrest. He was always going out at night, and Pinkerton was always following him, and his face was always turned toward the railroad, upon which he was sure to descend, and make examinations of the road about a mile and a half on both sides of the village. One day he had received some letters from New York, and Pinkerton watched him more closely than usual. About a quarter of a mile from the village was the graveyard, on a hill which commanded the railroad, and at dark the Englishman set out toward this wild and romantic spot, and Pinkerton after him. The night was cloudy, but every now and then the moon broke out and lighted up the lovely scenery. To Pinkerton’s amazement, he climbed the fence of the graveyard, and sat there looking towards the village, so that his “shadow” had to hide himself. Presently he jumped on a grave, and strode along towards the middle of the cemetery, with Pinkerton still after him, but dodging behind the trees and gravestones.

He could hear him muttering to himself, and occasionally talking aloud, and he stole up to him as near as he dared, and managed at last to creep into a vaulted grave close to him, one of the side slabs of which had fallen down. The dew was heavy, and the grass was so surcharged with it that he was wet through, but he kept on listening, and finally made out that he was reciting a soliloquy from Lord Byron’s “Manfred,” and occasionally gesticulating wildly to the moon. Was this man mad? What remorse had brought him here to vent itself in the terrible and dreadful lines of “Manfred”? At length he drew out his watch and tried to make out the time.

Then he jumped over the fence and ran down to the railroad. He was evidently waiting for somebody. For whom? Time would show, perhaps, for Pinkerton still followed him. Once he lost sight of him. Then he fancied he heard voices, and hurried in the direction from whence the sounds proceeded—and as he gained upon them, he found that his man was returning. So he skulked again, and the man went over to the churchyard. Here he stopped several times and listened. What had he been doing? Had he laid another trap for the overthrow of another train? It was a dreadful thought; and as it struck him the due train was heard in the distance. On it came, and no one to warn the engineer of the possible danger. In another moment it rushed past them, and went thundering on in the darkness. Then with all his soul in his ears, did the detective listen, expecting a crash every moment. But it was not to be.

The man watched it as it fled past, and then turned towards the village, and Pinkerton followed him to the hotel. He was all this time in secret conference with the superintendent of the railroad, who lived hard by. The next day, when Pinkerton called on him, he showed him a letter which he had received from someone who said he knew the gang that had thrown the last train over, and that they wanted to get him to join them, their object being to “cause more accidents” before long. He offered, for a consideration, to join them and become a spy on their actions for the company. Pinkerton advised the superintendent to employ the man, stipulating that he should be allowed to come to the office while the conference took place, in order that he might see and thus be able to identify him hereafter.

He had no doubt in his own mind who the man was. He was sure that he was the same person whom he had followed so often and so long up hill and down dale, and into the very jaws of death. And so it turned out. The man was engaged by the superintendent, and was in correspondence with a clerk in the post office in New York, who informed him whenever large sums were sent from that office west. This is a fact, however, which transpired subsequently when all was over with this very smart man who was so fond of playing the spy.

Mr. Pinkerton found that there was another man also in league with the “spy,” and that his work kept him chiefly in New York. Pinkerton now expected every day that there would be a “smash up”—but under the pretense that the company called him to New York, the “spy” left the West, and was gone so long that Pinkerton returned to Chicago.

About three weeks afterward he received another dispatch to go immediately to the old station, his expectation being realized in another overthrow and robbery of the mail train. On his arrival he found the same boot marks as in former cases, and was now satisfied that he had got the real criminal—for behold! he had returned to the hotel two days before the “accident” occurred, but he had the cunning to be in bed with some other person all that night, that he might be able to establish an alibi in case he was suspected. But still there was no legal proof against him. The boots never showed themselves on his legs, and Pinkerton even overhauled his room in search of them, but without effect. He found out, however, that he had a pair of strong and black-green boots which he wore on rainy days, and Pinkerton resolved to lay a trap for him on the next wet day, which happened during the same week the “accident” took place.

His trap was this. He persuaded the Superintendent to lay down fine red sand over all the paths to the office, and then to send for his spy, hoping that he would come in his hob-nails. They had not long to wait; for expecting a payment of money due him for services not rendered, he came wrapped up in a big coat, and having on those very boots that had been so long a mystery to the detective. This time there was no mistake. The red sand was pitted all over with the small-pox of those tell tale boots, and now the reader will think there was nothing to do but arrest the man. But what proof was there against him? Vivid circumstantial proof in abundance—legal proof none at all. Pinkerton had taken the precaution to make perfect casts and drawings of the impressions in the earth; and if he could get those boots into his possession, he might manage to scare the owner into a confession. However, he resolved to get him over to Chicago, under pretense of setting him on the person suspected of having a share in the late smash-up.

In this he was successful, through the cooperation of the superintendent; and strange to say, he carried his boots with him on the train. Pinkerton now made up his mind that he would have them by hook or crook. So at a midway station he got the conductor, who knew the “spy,” to invite him to take a drink with him; and when they were out together those boots in some quiet way found their place under Pinkerton’s carriage seat. On the arrival of the train at Chicago, Pinkerton followed his man until they got into a quiet street, and then arrested him, charging him point blank with throwing over the two trains in question, and also with the robbery of the Michigan Southern train some two years before. He shook in every limb, turned ghastly pale, and in half an hour, had made a full confession of his crimes. He owned that he and a friend robbed the mail at the collision between the Illinois Central and Michigan Southern, and said that they went to Europe and spent the money in eighteen months, when they returned, designing to make a regular trade of throwing trains off the track and robbing the mails. He was tried and convicted, and sentenced to the Jacksonville penitentiary for life, where he died after an imprisonment of over ten years.

Such, as near as I can remember the facts, is the story of these infamous transactions. There is not a word exaggerated, although I am pretty sure that I may be inexact in some of the minor details. And who was the criminal? What was the name of the wretch who could thus harden his heart to destroy his fellow creatures wholesale for the sake of a few thousand dollars? Reader, he was a natural son of Lord Byron, and called himself George Gordon August Byron. His mother is said to have been a Scotch lady, living in Edinburgh at the time of his birth, and a Stewart by name. His accomplice was a nephew of Charles Napier. There is no doubt about the truth of this story. Mr. Pinkerton is well known all over this continent, and in the capitals of Europe as a sort of Police Napoleon, who never lost any great case he undertook, and whose talents are only equaled by his integrity. It was he who has always recovered the moneys stolen from the Adam’s Express Company, and who saved President Lincoln’s life during his memorable journey to Washington, and it was the same great detective who, when yet a young man, worked up this Byron case.—N.Y. Evening Post.



Publishing Information

Published in
Fort Wayne Daily Gazette, September 1, 1871

Reprinted as
"The Hob-Nailed Shoes" in The Fitchburg [MA] Sentinel, September 2, 1871