Highwaymen of the Railroad
By William A. Pinkerton in 1893
The late 19th century witnessed a surge in audacious crimes that captivated and terrorized the nation: train robberies. This article, penned in 1893 by William A. Pinkerton of the renowned Pinkerton Detective Agency, offers a fascinating glimpse into the world of these "highwaymen of the railroad." Pinkerton, drawing upon his agency’s extensive experience, details the rise of this peculiar class of crime, the methods employed by the robbers, and the relentless efforts to bring them to justice.
Pinkerton notes that while train robberies had been a persistent problem in the South and West for two decades, the preceding months had seen an alarming increase, particularly in states south and west of the Missouri River. Texas, in particular, had become a hotbed for this "newest and just now most threatening form of crime." The article serves not only as a historical account but also as a call to action, urging for more effective measures to combat this growing threat to the nation’s railways and the safety of its citizens.
The Pinkerton Agency’s involvement in combating Highwaymen of the Railroad began with the notorious Reno brothers, who initiated their criminal careers immediately after the Civil War. These brothers, based in Seymour, Indiana, quickly became a terror to the local community. Their reign of terror was facilitated by a combination of intimidation, corruption, and the reluctance of local authorities to confront them. The Reno brothers’ story marks the beginning of Pinkerton’s experiences with train robbers.
The downfall of the Reno gang commenced in 1867 with the arrest of John Reno for robbing the county treasurer’s safe in Savannah, Missouri. He was abducted by masked men and forcibly transported to Missouri for trial, where he was convicted and sentenced to 25 years in prison. Later, Frank, William, and Sim Reno escalated their criminal activities, extending their train robberies as far west as Iowa. In a daring heist near Marshfield station, Indiana, they seized $80,000 from the Adams Express Company after overpowering the messenger.
The arrest and extradition of the Reno brothers sparked outrage in Seymour, Indiana, where the community had long been terrorized by their actions. In a dramatic turn of events, a vigilante group stormed the jail in New Albany, Indiana, and lynched the three Reno brothers and an accomplice, Charles Anderson. This act of extralegal justice was followed by the execution of other gang members and sympathizers in the vicinity of Seymour, effectively ending the reign of terror. In the aftermath, Seymour transformed into a model city, free from the scourge of train robberies, a stark contrast to the situation before the Reno brothers’ demise, when train robberies were a frequent occurrence. This is a testament to the impact of addressing the problem of Highwaymen of the Railroad decisively, although through controversial means.
Following the Reno brothers, Levi and Hillary Farrington, along with William Barton and William Taylor, emerged as prominent figures in the world of Highwaymen of the Railroad. Originating from western Tennessee, this gang met a violent end. Levi Farrington was apprehended in Farmington, Illinois, after a desperate resistance. Hillary Farrington and William Barton were captured near Venetta, Indiana Territory, after a posse stormed their hideout. William Taylor was arrested at Red Foot Lake in western Tennessee.
While being transported from Cairo, Illinois, to Columbus, Kentucky, Hillary Farrington attempted to murder Pinkerton, seizing a pistol from his overcoat pocket. In the ensuing struggle, Farrington fell overboard and drowned. Levi Farrington, considered the most desperate of the gang, was lynched by masked men in Union City, Tennessee, after being brought there for trial. His body was riddled with bullets. William Taylor and William Barton pleaded guilty and were sentenced to long prison terms in Tennessee, effectively dismantling the Farrington gang and bringing an end to train robberies in western Tennessee.
The James and Younger brothers of western and southwestern Missouri then rose to notoriety as Highwaymen of the Railroad. Their prominence stemmed from a robbery at Gad’s Hill on the Iron Mountain Railway, where they stole a large sum of money from the Adams Express Company. Prior to this, they had robbed the Hot Springs stagecoach, taking express money from its passengers. The Pinkerton Agency deployed Joseph Whicher, disguised as a farmhand, to infiltrate the James brothers’ circle. However, Whicher was quickly identified as a detective, captured, and murdered by Jesse and Frank James and their followers.
The pursuit of the James and Younger brothers continued with Captain Lull, who killed John Younger and wounded Jim Younger, only to be fatally shot by Jim. The Younger brothers, Coleman, Jim, and Robert, were eventually arrested and convicted for the murder of a bank cashier in Northfield, Minnesota, and sentenced to life imprisonment. Jesse James was later killed by Robert Ford, a member of his own gang, while Frank James surrendered and purportedly lived an honest life thereafter. The Ford brothers, who killed Jesse James, were controversially pardoned after being sentenced to death, and were given the reward for James’s capture.
Sam Bass, along with the Collins brothers and others, led another gang that targeted the Pacific Express on the Union Pacific Railroad, stealing approximately $60,000 in gold. The Highwaymen of the Railroad stopped the train, forced the crew to disembark, and looted the safes, seizing money, watches, and jewelry. However, their criminal enterprise was short-lived. Joel Collins was killed, and a confederate named Berry was shot dead near Moscow, Missouri, with the stolen money recovered.
Sam Bass escaped to Denton County, Texas, where he had many supporters who were unwilling to provide information about his whereabouts. In Texas, he formed a new gang of train robbers. The United States government, in collaboration with detectives, devised a plan to lure the gang to Round Rock, Texas, to rob a bank. However, the plan was prematurely triggered by a local officer, leading to a shootout in which most of the gang members were killed or captured. The incident highlights the common pattern of train robbers operating in familial groups, with multiple members of the same family involved.
Jim and Rube Burrow of Alabama perpetrated a series of train robberies, though they never acquired significant sums of money. The Highwaymen of the Railroad were eventually apprehended by Pinkerton agents working for the Southern Express Company. Jim was arrested in Savannah, California, while Rube escaped after shooting two men. Jim was sentenced to Arkansas State Prison, where he died. Rube, with accomplices, robbed a train at Duck Hill, Mississippi, and another in Florida, before being captured by local officers aided by Southern Express detectives.
Fred Wittrock of Leavenworth, Kansas, executed a daring express robbery on the St. Louis & San Francisco Railroad near St. Louis, Missouri. He presented a fraudulent order to the messenger and, after binding and gagging him, stole approximately $50,000. Wittrock was apprehended in Chicago by Robert A. Pinkerton and detectives. He was extradited to Missouri, sentenced to seven years in prison, and surrendered the unspent money. The swift capture of Wittrock and his accomplices underscored the effectiveness of coordinated law enforcement efforts.
The Dalton brothers emerged in Kansas and the Indian Territory (Oklahoma), conducting numerous train robberies across the country. The Highwaymen of the Railroad’s operations spanned from Missouri to the Pacific Coast. While some gang members were captured but escaped from jail, the rest of the gang was killed. The Dalton brothers’ story highlights the persistent challenge of apprehending and containing these criminal elements.
Albert Denton Slye, Marion Hedgepeth, Dink Wilson, and Tom Francis robbed the Adams Express on the St. Louis & San Francisco Railroad near Pacific, Missouri, obtaining about $15,000. Slye was apprehended in Los Angeles, California, with evidence linking him to the crime. He pleaded guilty and was sentenced to twenty years. Hedgepeth was arrested in San Francisco after receiving mail under an alias. Francis and Myers were killed while attempting to rob a train near Ft. Scott, Kansas. Hedgepeth was convicted and sentenced to twenty-five years in the Missouri State Prison. Wilson, after hiding in the mountains near Utah, was identified as a murderer in Syracuse, New York, and subsequently arrested.
The Sontag brothers and Chris Evans, who were also Highwaymen of the Railroad, robbed an American Express train on the Chicago, Milwaukee & St. Paul Railroad. They later robbed a Wells Fargo train on the Southern Pacific Railroad in California. One of the Sontag brothers was arrested, but Evans and the other Sontag escaped after shooting officers. They were later captured, with Sontag killed and Evans badly wounded.
In a robbery on the Mineral Range Railway, the Hoagan brothers and three others stole about $70,000 from the American Express Company but were quickly apprehended, and the money was recovered. The article concludes with a discussion of the factors contributing to the rise in train robberies, including economic depression and the influence of sensational novels. Pinkerton advocates for federal legislation to address train robbery, arguing that local authorities are often hampered by sympathy for the robbers. He emphasizes the importance of relentless pursuit by express companies and suggests measures such as higher money rates to encourage banks to use the U.S. mails and improved security measures on trains. The issue of Highwaymen of the Railroad demanded a comprehensive approach.
Pinkerton emphasizes the need for stronger laws and more effective law enforcement to combat this growing threat. He notes that express companies are considering raising rates to encourage banks to use the U.S. mails, thereby making train robbery a federal offense. He also highlights the importance of armed guards and burglar-proof safes on trains. Ultimately, Pinkerton calls for a concerted effort to protect the nation’s railways and ensure the safety of its citizens, as train robbery was 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.