Highwaymen of the Railroad

John Sontag

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, Minnesota 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 in 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 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

Train Robbery

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 anyone 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, anyone 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 offense.

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.

The members of the Wild Bunch were aggressively pursued by Pinkerton Agents.

The members of the Wild Bunch were aggressively pursued by Pinkerton Agents.

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 is landed in prison or killed, train robberies would be more frequent. A man who will rob an express company is a fugitive forever afterward 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 offense. 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 anyone until their arrival at Chicago or another 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 December 2019.

Allan Pinkerton, 1862

Allan Pinkerton, 1862

Also See:

The Pinkertons – Operating For 150 Years

Railroad in the American West

Historical Accounts of American History

Old West Main Page

Train Robberies in America

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.