Highwaymen of the Railroad

By William A. Pinkerton in 1893

Train Robbery

Train Robbery

The recent epidemic of train robbing in different sections of the country has naturally caused considerable discussion about the best means of checking this peculiar class of crime. Train robbing has been practiced pretty steadily in the South and West during the last 20 years, but during the last few months, outrages of this character have increased at an alarming rate. The greater portion of these occurred south and west of the Missouri River. More than any other state, Texas has suffered from this newest and just now most threatening form of crime.

My experience with train robbers began with the earliest operations of these daring criminals. There were no train robberies of any importance before the war. The first our agency had to do with were perpetrated by the Reno brothers of Seymour, Indiana.

Four of these brothers became noted as train robbers. They commenced their robberies immediately after the war and became terrors to the community in which they lived. It was impossible to get the necessary evidence to convict them. To a certain extent, they controlled, through terrorizing, some of the local judges; and the local authorities, either through sympathy or fear, were afraid to do their duty.

Frank Reno (left) and John Reno (right)

Frank Reno (left) and John Reno (right)

The downfall of this gang commenced in 1867 with the arrest of John Reno, who, in company with others, had robbed the county treasurer’s safe at Savannah, Missouri. He was tracked back to Seymour, and, as there was no chance of his being extradited, a party of masked men went into Seymour and bodily carried him on board a train that was about to start for Missouri where he was convicted and sentenced to 25 years of imprisonment. Later on, Frank, William, and Sim Reno committed several train robberies throughout Indiana, extending their operations as far west as Iowa. In the winter of 1868, they “held up” a train near Marshfield station, Indiana, forced their way into the Adams Express car, threw the messenger from the car while the train was under headway, and robbed the Express Company of $80,000. Sim and William Reno were arrested at Indianapolis. Frank Reno and Charles Anderson, another of this gang, were also arrested at Windsor, Canada. After bitterly contesting their extradition in all the courts of Canada, they were finally brought to Indiana and confined in the jail at New Albany. The people in the vicinity of Seymour became aroused because war had actively commenced against the Reno brothers, and, as these men had terrorized them for years, they were willing to take a hand in exterminating them.

One stormy night the jail at New Albany was surrounded by a band of masked men, the sheriff and jailer were overpowered, and the three Renos and Anderson were taken from their cells and hanged in the corridors of the jail. Their execution was rapidly followed by that of the other members of the gang, their sympathizers, and abettors, who lived in the vicinity of Seymour, no less than nine being hanged by the vigilance committee. For years after that, and, up to the present time, Seymour, Indiana, has been noted as a model, flourishing city, and I do not recall a single case of train robbing in southern Indiana since the execution of the Renos. In contrast, previous to this a train was usually robbed there about every 60 days.

Farrington Brothers

Farrington Brothers

Levi and Hillary Farrington, William Barton, and William Taylor committed the next train robbery of any importance. These people came from western Tennessee. After making a desperate resistance, Levi Farrington was arrested by us at Farmington, Illinois. We arrested Hillary Farrington and William Barton near Venetta, Indiana Territory. A posse surrounded the house where they were hiding, the door was broken down, and the house fired when they were compelled to come out with their “hands up.” Our men arrested William Taylor at Red Foot Lake in western Tennessee. While conveying Hillary Farrington and William Barton from the Indiana Territory to Union City, Barton made a complete confession as to the other gang members and what had been done with the proceeds of the robberies.

While traveling from Cairo, Illinois, to Columbus, Kentucky, I was about to enter the barroom of the steamer when Hillary suddenly seized a large pistol that was sticking from my overcoat pocket and tried to conduct a murderous assault on me.

During the struggle which ensued for the possession of the pistol, Hillary Farrington fell over the low railing of the boat, nearly dragging me with him, and was drowned. Levi Farrington was the most desperate of the gang. When he was brought to Union City, Tennessee, the citizens held a jollification meeting, as he had shot and killed a marshal and his deputy in eastern Missouri and a deputy sheriff in Tennessee.  About two o’clock in the morning, fifty masked men came to the house where he and the other prisoners were under guard, as the town jail was not strong enough to hold them. They overpowered the guards, dragged out a man who had attempted to rescue Farrington, and hanged him. Levi Farrington was shot in his room, his body fairly riddled with bullets. William Taylor and William Barton pleaded guilty and were sentenced to long terms of imprisonment in Tennessee.

Train Robbery

Train Robbery

The capturing and sentencing of the members of this gang were the means of breaking up train robberies in western Tennessee. There has not been a train robbery in that vicinity since 1871, the date of the execution of these men. The Farringtons were among the most desperate of this class of men I have ever known and were as successful as any of the desperadoes engaged in “holding up” and robbing trains.

The next train robbers of any importance were the James and Younger brothers of western and southwestern Missouri. The robbery that brought them into prominence occurred at a small station on the Iron Mountain Railway, known as “Gad’s Lull,” where they “held up” the train and got a large amount of money from the Adams Express Company’s safe. This was in 1873. A short time previous to this, they had robbed the safe of the Hot Springs stagecoach, holding up the coach with its twelve passengers and taking all the express money. One of our best men, Joseph Whicher, was detailed to go to the neighborhood of the home of the James boys and obtain work as a farmhand. He was dressed up as a farmer, his hands being hardened and his skin darkened to complete the disguise.

About dark, he approached the home of the James’, knocked at the door, and applied for work. Mrs. Samuels, the mother of the James brothers, opened the door, who invited him in and gave him a chair.

While he was seated, the door was suddenly thrown open, and he was confronted by Jesse and Frank James and some of their followers, who entered and accused him of being a detective. This he denied. The Jameses, however, said they were at war with all police officials and taking him from the house, gagged and bound him, tied him to a horse, and took him across the old Blue Mill Ferry, telling the ferryman that he (Whicher) was a horse thief, whom they were going to deliver up to the authorities.

James-Younger Gang

The James-Younger Gang – Left to right: Cole” Younger,
Jesse Woodson James, Bob Younger, and Frank James.

They took him to within about five miles of Independence, Missouri, and murdered him by shooting him in the back. Captain Lull, who searched for the Younger brothers in St. Clair County, Missouri, shot and killed John Younger and wounded his brother, Jim Younger, but was himself shot by the latter and died from his wounds. Jim Younger is at present in the Minnesota Penitentiary. But, it is said, he never recovered from the wounds received at Captain Lull’s hand. It now became a war of extermination on the part of the express companies and our officers against the remnant of this gang. The three Younger Brothers, consisting of Coleman, Jim, and Robert, were arrested and convicted for the murder of bank cashier Haywood at North Northfield, Minnesota, and were sentenced to life imprisonment. Shortly after this, Jesse James was shot and killed by Robert Ford, the youngest member of his gang.

Robert and Charles Ford were arrested and pleaded guilty to the killing of Jesse James and were sentenced to be hanged but were immediately pardoned by Governor Crittenden, and they were paid the reward of 5,000 which had been offered for the arrest of  Jesse James, dead or alive. This was according to an arrangement the Ford brothers had made with the Governor. After this, Frank James surrendered and, as far as I am advised, has been living an honest life since.

Union Pacific engine

The next gang that made its appearance was 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 gang members 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 many friends, being situated therein very much the same way as the James brothers in Missouri, nobody was willing to give any information concerning him.

In Texas, he organized another gang of train robbers. These men perpetrated several 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, to rob 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 them for carrying firearms, not knowing of the plans 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.

Rube Burrow

Rube Burrow

Brothers Jim and Rube Burrow of Alabama perpetrated the next series of train robberies. These men, in company with several others, “held up” several trains but never succeeded in getting much money.  All three 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 afterward, 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, perpetrated a few miles outside of St. Louis, Missouri, by Fred Wittrock of Leavenworth, Kansas. Wittrock had planned the robbery for some time and had taken several 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. However, he was arrested in Chicago by Mr. Robert A. Pinkerton and two of our detectives, and the balance of the gang was 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.

Daltons Dead

Daltons Dead

About this time, the Dalton brothers made their appearance in Kansas and the Indian Territory (Oklahoma.) 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 afterward succeeded in escaping from jail. The whole gang was shot down except for one brother 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.

Our agency worked with the St. Louis, San Francisco, and Los Angeles police forces. Robert A. Pinkerton, Detective Whittiker, and an officer in Los Angeles arrested Slye in Los Angeles, California.

On his person was found the watch taken from the express messenger and a ring 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 hid 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 several burglaries that 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 the local officers arrested him. 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.

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. Our agency, acting for the American Express Company, was 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. With the aid of the local officers, our agency 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. Still, I feel confident that the officers engaged in this will eventually get the right people. One thing certain is 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 primarily 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 willing to go into their schemes. Most 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 17, 21, and 16 “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 train conductor 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 70 years each in state 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 frequently the penalty. The chances of escape are not one in a hundred, and the stealings, as a rule, are very small despite the widespread 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. However, it has been employed in several 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 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.”

No one will deny that this particular form of crime is on the increase. 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. A meeting of the general managers of the different railroads centering in a Western city was recently held to adopt 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 I had brought with me. 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 he couldn’t 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 no authority to go further. A state or county line would not be 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. Still, it is not right that these companies should be obliged to take these steps and go to the great expense they are frequently obliged 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 they arrive at Chicago or another destination point, the messenger not knowing the combination.

Written by William A. Pinkerton 1893, Compiled and edited by Kathy Alexander/Legends of America, updated December 2021.

Allan Pinkerton, 1862

Allan Pinkerton, William’s father, 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. The text that appears here has been edited for punctuation and updated for the modern reader.