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Highwaymen of the Railroad - Page 2

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The next gang that made its appearance was one headed by Sam Bass, the Collins brothers and others. They "held up” and robbed the Pacific Express on the Union Pacific Railroad and got about $60,000 in gold. Two of this gang stopped the train, compelled the crew to alight together, while they went through the safes, taking everything in sight, money, watches and jewelry. Their career, however, was brief. Joel Collins was shot and killed; one confederate named Berry was shot and killed near Moscow, Missouri, arid all the money recovered. Sam Bass succeeded in making his escape, and went to Denton County, Texas, where he had a great many friends, being situated there in very much the same way as the James brothers in Missouri, nobody being willing to give any information concerning him.


In Texas he organized another gang of train robbers. These men perpetrated a number of train robberies in Texas, but the United States government took hold of the matter in conjunction with the detectives and arranged a plan for luring the gang to Round Rock, Texas, for the purpose of robbing a bank.


The bank was carefully covered by armed men secreted wherever men could be put without attracting attention. When the gang appeared near the bank the fight was opened prematurely by a local officer, who attempted to arrest one of the number for carrying firearms, not knowing of the plans which had been made. The fight thus commenced, the concealed officers ran into the street and opened fire on the gang with their Winchesters, killing most of them and taking the others prisoners. One thing will be noticed about train robbers, they generally go in families, that is, there are usually two or three members of one family in the same gang.


Union Pacific Engine

Union Pacific Engine coming out of the roundhouse, H.C. White, 1905.

This image available for photographic prints and downloads HERE!






Rube Burrow, train robberThe next series of train robberies were perpetrated by Jim and Rube Burrow, of Alabama. These men, in company with several others, "held up” a number of trains, but never succeeded in getting much money.  All three of the men were after-wards arrested by our men acting for the Southern Express Company, tried and convicted in Texas. Rube and Jim Burrow were surprised by the local officers in Savannah, California; Jim was arrested, but Rube was not taken so easily. He shot down two men in Savannah, one of whom died afterwards, but he succeeded in getting away. Jim was turned over to our men, who took him to Arkansas for his part in robbing the Southern Express Company. He was sentenced to Arkansas State Prison, where he died. Rube Burrow, in company with two others, "held up” a train at Duck Hill, Mississippi, on the Illinois Central Railroad. Both he and his companions succeeded in making their escape to the mountains of Alabama. He held up another train in Florida to which was attached a Southern Express car. The Southern Express and their detectives followed him persistently and finally caused his arrest by the local officers.

Then came the daring express robbery on the St. Louis & San Francisco Railroad, which was perpetrated a few miles outside of St. Louis by Fred Wittrock, of Leavenworth, Kansas. Wittrock had planned the robbery for some time and had taken a number of people into his confidence, but they weakened when they saw the risk they had to take. He then went alone to commit the robbery. Wittrock presented an order to the messenger purporting to be from the route agent of the Adams Express Company for that division, asking the messenger to "break him in.” When out a little way on the road, he plugged the bell cord, threw the messenger on the floor, bound and gagged him and then rifled the safe of its contents and succeeded in getting away about 50,000.


Under the name of Jim Cummings he subsequently wrote several letters to the St. Louis papers stating that the robber would never be discovered. He was, however, arrested in Chicago by Mr. Robert A. Pinkerton and two of our detectives and the balance of the gang were all captured. Wittrock was extradited to Missouri and sentenced to seven years imprisonment in the penitentiary. He gave up all the money he had not spent. Everybody connected with this robbery had been located almost immediately after it was committed with the exception of Wittrock, who was caught about forty days after the robbery. When arrested he was heavily armed and would have made a desperate resistance had he not been taken by surprise.


The Dalton Gang killedAbout this time the Dalton brothers made their appearance in Kansas and the Indian Territory . These men, five in number, "held up” numerous trains throughout the country. Their base of operations extended from Missouri to the Pacific Coast. Several of them were taken into custody, but afterwards succeeded in making their escape from jail. The whole gang was shot down with the exception of one brother who is now in Kansas, and who is supposed to be the leader of a new gang operating under the old name "The Daltons.”


The next robbery of any note was that of the Adams Express on the St. Louis & San Francisco Railroad, near Pacific, Missouri, by Albert Denton Slye, Marion Hedgepeth, Dink Wilson and a man named Tom Francis. They obtained about 15,000 by this robbery.


The case was worked by our agency in conjunction with the St. Louis, San Francisco and Los Angeles police forces. Robert A. Pinkerton, Detective Whittiker, and an officer in Los Angeles arrested Slye at Los Angeles, California.


On his person was found the watch taken from the express messenger and a ring that was known to have been in the express safe. Slye pleaded guilty and was sentenced to twenty years. Later on I received information that Hedgepeth was receiving mail under an alias at San Francisco, California. This information was communicated to the San Francisco police, who arrested Hedgepeth a few days later as he was calling for his mail at the post-office. Shortly after this Jim Francis and a man named Myers, members of this gang, attempted to "hold up” a train near Ft. Scott, Kansas, but were overpowered and killed. Hedgepeth fought his case bitterly in the courts, but was finally convicted and sentenced to twenty-five years in the Missouri State Prison. Dink Wilson, the other member of this gang, escaped, went into the mountains near Utah, and was in hiding for a long time. Last July while a detective at Syracuse, New York, was trying to arrest two men who were suspected of being connected with a number of burglaries which had occurred in the neighborhood of Syracuse, the men turned and fired at short range, killing him almost instantly. One of the murderers was taken, but the other escaped. The picture of the man arrested was sent throughout the country, and was finally identified as that of Dink Wilson. We subsequently located the second man at Buffalo, where he was arrested by the local officers. These two men are bound to be convicted, and will, in all probability, be electrocuted. This will dispose of this whole gang of train robbers.


The two Sontag brothers and [Chris] Evans were the next train robbers to spring into prominence. They operated as far East as Racine, Wisconsin They "held up” a train on the Chicago, Milwaukee & St. Paul Railroad, robbing the American Express Company of a large amount of money. After this robbery they decamped to Minneapolis, and there our agency, acting for the American Express Company, were put on their track, but did not have sufficient evidence to arrest them. We, however, followed them to California, where they "held up "a train on the Southern Pacific, robbing the Wells-Fargo Company’s safe. One of the Sontag brothers was arrested, but Evans and the other Sontag succeeded in escaping after shooting all the officers. They were, however, recently captured and in the encounter Sontag was killed, and Chris Evans is now awaiting trial, badly wounded.

In the recent train robbery on the Mineral Range Railway the robbers succeeded in getting about $70,000, the property of the American Express Company. This robbery was committed by two brothers named Hoagan and three others. Our agency, with the aid of the local officers, speedily captured these men and recovered all the money. The last robbery of the United States Express Company, on the Lake Shore & Michigan Southern Railway, has not yet been worked up, but I feel confident that the officers engaged on this will eventually get the right people. There is one thing certain, that the men engaged in the last express robbery will not be allowed to escape.


One of the reasons for the recent epidemic of train robberies  may be found in the general business depression. It is, however, also largely due, in my opinion, to the reading of yellow-covered novels. Country lads get their minds inflamed with this class of literature. Professional thieves or designing men find among this class many who are willing to go into their schemes. The majority of these robbers are recruited from among the grown boys or young men of small country towns. They start in as amateurs under an experienced leader. They become infatuated with the work and never give it up until arrested or killed. I recollect a case where three boys aged respectively seventeen, twenty-one and twenty-six "held up” a train near Emmett, Arkansas, in 1882 and took from the Pacific Express about $9,000 and from the passengers about $1,500. The conductor of the train ran one of them down and brought him back, the other two escaped, but were eventually arrested in the Indian Territory. They were convicted and sentenced to seventy years each in state’s prison. One of these was a mere lad, who had seen a railway train for the first time to "hold it up.”


Train robbery is not a profitable pursuit by any means. In nearly every case capture and punishment are almost certain, and death is very frequently the penalty. The chances of escape are not one in a hundred, and the stealings as a rule are very small in spite of the popular belief that train robbers succeed in getting large sums of money without being caught. Until three years ago dynamite was never used in train robberies. It has been employed, however, in several of the more recent cases, and its use makes train robberies all the more dangerous. The robbers can now blow open an express car in a few seconds, where formerly it took them several minutes to pick the lock or force the combination. Speaking on this point the General Manager of the St. Louis & San Francisco Railroad said recently:


I frequently receive suggestions to have steel express cars built and to send guards with trains. But why should we do that when any one may buy a quarter’s worth of dynamite, and blow to pieces the strongest metal ever put together? Great treasure is carried by every line, and dynamite will open the best of safes. In many states any one may buy that dangerous explosive, and no questions are asked. Law should first restrict the sale of it, as it does the sale of poison. Men who hold up passenger trains are armed, and, if it is necessary to carry out their designs, they will kill. Aside from the liability of a messenger, an engineer, or a curiously inclined passenger to be shot, there is a greater danger that another train may come along and wreck the passenger train, standing alone on the track, in some dark cut or lonely piece of woods. Train robberies are increasing each year, and I shall bend my energies to procure legislation making train robbery a capital offence.


That this peculiar form of crime is on the increase no one will deny. That it should be checked promptly and firmly is imperative. Indeed, unless some measures are taken to prevent the increase of train robberies I would not be surprised to see an express train held up within ten miles of New York or Philadelphia at a not very remote date. The question is a very serious one. In fact a meeting of the general managers of the different railroads centering in a Western city was recently held for the purpose of adopting some means of defense against these desperadoes.


The bill recently introduced in the House of Representatives by Congressman Caidwell, of Ohio, which proposes to place the crime of train robbery under the jurisdiction of the United States, has great merit, and should be passed without delay. If it becomes a crime against the United States to "hold up” and rob a train, it is almost certain that this class of work will soon come to an end. The robbers frequently have friends or relatives among the local authorities in the county in which they reside, and more particularly is this so in the South and Southwest. A Western officer once told me, when I asked his assistance to arrest a part of a train-robbing gang, that he would deputize me and aid me secretly, but owing to the relatives and sympathizers of these  men residing in the county he dare not lend a hand openly; that J did not reside in the county and did not have to live there after this arrest was made, but he did. He deputized me and one of our men whom I had brought with me, and that night he rode with us into the Missouri River "bottoms” and pointed out the home of the men we wanted, helped to surround the house, and was ready to kill either of the men if necessary, providing it was not known that he helped to do so. This man was a good officer and willing to do his duty, but it was impossible for him to conduct a fight against these men alone. Had it been known that he was against them he would have been assassinated. This itself is a good argument why the United States government should take charge of these cases, as the robbers are not likely to be able to control the United States officials as they control the local authorities. The latter will frequently drop pursuit at the state or county lines, claiming that they have no authority to go further. A state or county line would not act as a barrier for a United States officer. I hope, therefore, that Congress may see the necessity of taking some action on the bill now before them.


If it were not for the prompt and energetic action of the express companies in persistently following up train-robbing gangs and never giving up the search until all the gang are landed in prison or killed, train robberies would be more frequent. A man who will rob an express company is a fugitive forever afterwards until arrested or punished, as express companies are relentless in pursuing those who rob them; but it is not right that these companies should be obliged to take these steps and go to the great expense that they frequently are obliged to go to in order to arrest or exterminate these highwaymen. They are as much entitled to protection under the law as is a private individual, but, being corporations, they do not get this protection, but are obliged to spend large amounts of money to protect themselves.


Express companies which carry large sums of money are seriously considering the advisability of placing the money rates so high that the banks will be forced to use the United States mails for the transport of their money, so that the robbers, to get the money, must " hold up” the United States mails as well as the express companies, thus making such a robbery a government offence. The express companies are now carrying on their heavy money trains guards armed with the latest improved style of revolvers and Winchesters. These guards are men known for their determination and nerve, and will most likely give a warm reception to the next gang that attempts to rob a train anywhere in the  country. The express companies are also placing burglar proof safes in their cars. These safes are strongly constructed, so it will take the robbers hours to get into them, and if they are blown up the money will be destroyed so that it will not do the robbers any good. The safes are locked in New York and cannot be opened by any one until their arrival at Chicago or other point of destination, the messenger not knowing the combination.


Written by William A. Pinkerton 1893, Compiled and edited by Kathy Weiser/Legends of America, updated March, 2017.


William Pinkerton and railroad special agents

William Pinkerton and railroad special agents, late 1870s



Highwaymen of the Railroad, written by William A. Pinkerton of the Pinkerton Detective Agency, appeared in The North American Review in November, 1893.  The Pinkerton Agency was founded by William's father, Allan Pinkerton, a Scottish immigrant in 1850. Quickly, he became one of the most important figures in crime detection and law enforcement during the latter half of the 19th century. Both William and his brother Robert worked at the agency, eventually taking it over after their father died in 1884. Though no longer family run, Pinkerton's Inc.is still in business today.



Also See:


The Pinkertons - Operating For 150 Years

Railroad in the American West

Historical Accounts of American History

Old West Main Page



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