Famous Train Robberies in History: Uncovering Legendary Heists

Train robberies have fascinated people for generations, capturing the wild and daring spirit of a bygone era. These acts were often carried out by infamous outlaws who became larger-than-life figures in history. One of the most famous train robberies in the United States took place on June 12, 1924, when the Newton brothers’ gang executed the biggest train heist in American history at Rondout, Illinois.

In the late 19th century, the Wild West was rife with train robberies, often orchestrated by gangs like the Dalton Gang and figures such as Butch Cassidy and Jesse James. These robberies were not just about the money but also about the thrill and the audacity of defying the law. The Dalton Gang, for instance, gained notoriety after successfully robbing a Missouri-Kansas-Texas Railway express car, showcasing their bold approach to crime.

Even earlier, Jesse James and the James-Younger Gang became infamous for their well-planned train heists, including an 1873 robbery where they made off with $3,000 from a Rock Island Railroad train. These stories highlight the adventurous yet dangerous nature of train robberies, cementing their place in the annals of history.

Photo: A portrait of Jesse James.

Historic Context of Train Robberies

Train robberies were a significant part of American history, especially in the late 19th and early 20th centuries. These events were influenced by various social and economic factors, including the aftermath of the Civil War and the expansion of the railroads into the American West.

The Rise of Train Robbery in the American Old West

In the late 1800s, the expansion of railroads across the United States provided new opportunities for criminals. The vast, often unpatrolled territories of the West became fertile ground for brazen train robberies. The Reno Gang, in 1866, carried out one of the first major train robberies in American history, signaling the start of a new era of banditry.

Butch Cassidy poses in the Wild Bunch group photo, Fort Worth, Texas, 1901
Butch Cassidy poses in the Wild Bunch group photo, Fort Worth, Texas, 1901

Butch Cassidy and his Wild Bunch were notorious for their well-planned heists. They exploited the isolated railways and the relatively weak law enforcement in the frontier regions. Their robberies were often romanticized, depicting them as clever outlaws outwitting the system. The Dalton Gang also gained notoriety with several high-profile train heists during this period.

Train robberies during the Wild West era were often violent and daring, involving shootouts and high-speed chases. The stolen loot ranged from cash and gold to other valuable cargo, and these crimes fed into the mythos of the American frontier.

Impact of the Civil War on Train Robberies

The Civil War had a profound impact on the rise of train robberies in the United States. During the war, railroads were crucial for transporting troops and supplies. They became strategic targets for both Union and Confederate forces, who often sabotaged tracks and looted trains. This wartime activity laid the groundwork for post-war criminal enterprises.

After the war, many soldiers found themselves unemployed and disenfranchised. Some turned to crime, including train robbery, as a means of survival. The skills they had developed in guerrilla warfare translated well into the illegal tactics used in train heists. The famous Jesse James and his gang, comprised of former Confederate guerrillas, were among the most infamous train robbers of the time.

The era also saw the rise of the Pinkerton National Detective Agency, which was often hired by railway companies to thwart these robberies. This cat-and-mouse game between the robbers and law enforcement added to the drama and danger surrounding train robberies in post-Civil War America.

Notable Train Robbers and Gangs

Throughout history, several infamous figures and groups have become notorious for their audacious train heists. This section delves into the lives and crimes of these notable train robbers and gangs.

Butch Cassidy and the Wild Bunch Gang

Butch Cassidy, born Robert LeRoy Parker, led the Wild Bunch Gang, a loose association of outlaws. They are famous for robbing banks, trains, and breaking laws across the western U.S. One of their most daring train heists occurred on June 2, 1899, when they robbed the Union Pacific Overland Flyer No. 1. Butch Cassidy and his gang became legendary for their ability to elude law enforcement, contributing significantly to their enduring infamy.

Jesse James and the James-Younger Gang

Jesse James, along with his brother Frank, formed the James-Younger Gang. They earned their place in history with a series of bank and train robberies in the 1860s and 1870s. One of their most notable train robberies was the 1873 heist in Adair, Iowa. The gang derailed the Rock Island train, looted its contents, and terrorized passengers. Jesse James quickly became one of the most legendary and controversial figures in American outlaw history.

Frank Reno 1837-1868
Frank Reno 1837-1868

Reno Brothers: The First Big Name Train Robbers

The Reno Brothers, consisting of Frank, John, Simeon, and William Reno, are often credited with conducting the first peacetime train robbery in the United States. On October 6, 1866, they stopped an Ohio & Mississippi train near Seymour, Indiana, and stole a cache of money amounting to about $13,000. This robbery marked the beginning of a series of thefts that would establish their notoriety. Their brazen acts inspired other outlaws and paved the way for future train robberies.

The Dalton Gang’s Transition from Lawmen to Outlaws

The Dalton Gang, originally composed of law-abiding brothers, transitioned into a life of crime in the early 1890s. Members included Bob, Grat, and Emmett Dalton. They achieved notoriety by robbing banks and trains. One of their significant robberies occurred in May 1891, when they successfully held up a train and stole $1,745. Despite their criminal success, their downfall came quickly as law enforcement efforts intensified. The Dalton Gang’s violent shift from lawmen to outlaws remains a dramatic tale in American history.

The Infamous Deautremont Brothers

The DeAutremont brothers—Hugh, Ray, and Roy—are infamous for their botched attempt to rob Southern Pacific’s “Gold Special” train in 1923. The brothers’ poorly executed heist resulted in the deaths of four men, including the train’s engineer and fireman. Despite their initial escape, extensive manhunts eventually led to their capture. The brutality and failure of their robbery ensured their place in the annals of train robbery history, serving as a grim reminder of the violence associated with such crimes.

The Newton Boys and Their Aftermath

The Newton Boys, a gang led by Willis, Joe, Jess, and Dock Newton, were among the most successful train robbers in American history. They conducted a series of heists in the 1920s, most famously robbing a mail train near Rondout, Illinois, in 1924, stealing over $3 million. Their approach was less violent than other gangs, focusing on meticulous planning and execution. Despite their ultimate capture and imprisonment, the Newton Boys’ legacy persisted as one of the most lucrative train-robbing gangs in history.

Famous Train Robbery Heists

Many train robberies throughout history have captured public attention due to their daring execution and significant impact. From the Wild West to more modern occurrences, these events have become legendary.

The Great Train Robbery of 1903

In 1903, the Great Train Robbery took place in the United Kingdom. The thieves targeted a Royal Mail train traveling from Glasgow to London. They executed a well-planned heist, stopping the train and making off with a huge sum of money.

Their meticulous planning involved tampering with the signals to halt the train in a secluded area. Although many were caught, the haul was substantial, leading to sensational media coverage.

The Wilcox Train Robbery by Butch Cassidy’s Wild Bunch

In the late 19th century, Butch Cassidy and his Wild Bunch carried out the Wilcox Train Robbery. They targeted a Union Pacific Overland Flyer No. 1 near Wilcox, Wyoming, on June 2, 1899.

The gang managed to stop the train, blow open the safe, and escape with around $60,000. This robbery bolstered their notoriety and was detailed in many newspapers.

Rondout, Illinois Train Robbery by the Newton Gang

The Rondout Train Robbery took place on June 12, 1924. Led by the Newton Gang, the robbers managed to steal over $3 million in cash, bonds, and jewelry.

This heist is considered one of the largest in U.S. history. The gang used inside information and orchestrated a near-perfect execution to halt and loot the train in Rondout, Illinois.

The Southern Pacific 17 Train Heist by the Deautremont Brothers

The Deautremont Brothers carried out the Southern Pacific 17 Train Heist on October 11, 1923. They targeted the Southern Pacific Railroad’s express train near Siskiyou, Oregon, intending to loot the mail car.

Their attempt was poorly planned, resulting in the deaths of four train employees but leading to little profit. This brutal robbery received widespread attention at the time.

Early photo of the railroad depot at Fairbank, Arizona. Circa 1900.
Early photo of the railroad depot at Fairbank, Arizona. Circa 1900.

Fairbank Train Robbery and the Black Hills Bandits

The Fairbank Train Robbery involved the Black Hills Bandits, also known as the High Fives. It occurred in Fairbank, Arizona, on February 15, 1900.

The bandits tried to steal the express car funds but were thwarted when Jeff Milton, a trusted lawman, defended the train. Though wounded, Milton managed to secure the train’s shipment, and the robbers fled empty-handed.

The Canyon Diablo Train Robbery

The Canyon Diablo Train Robbery happened near Canyon Diablo, Arizona, in 1889. This heist involved a gang led by outlaw Ben Tasker. They successfully flagged down a train and overpowered the crew.

The gang stole a significant amount of cash and valuables before disappearing into the wilderness. Despite efforts to capture them, the robbers evaded arrest, cementing their story in train robbery lore.

 Reynolds (far right) at Ronnie Biggs' (far left) 70th birthday with their sons
Reynolds (far right) at Ronnie Biggs’ (far left) 70th birthday with their sons

The Canyon Diablo Train Robbery (1963)

The Great Train Robbery of 1963 was a famous heist in the United Kingdom where a gang of robbers targeted a Royal Mail train traveling from Glasgow to London. The robbery took place in the early hours of August 8, 1963, near Bridego Railway Bridge in Buckinghamshire, England.

The robbers, led by Bruce Reynolds, planned the heist meticulously. They tampered with railway signals to stop the train, and then overpowered the driver, Jack Mills. The gang managed to load 120 mailbags containing £2.6 million (equivalent to about £53 million today)

Techniques and Tactics Used in Train Robberies

Train robberies often included the use of explosives, moving heists, and clever diversions. These tactics were crucial to the success of many notorious robberies.

Role of Dynamite and Explosives

Robbers often used dynamite to blow open train safes and strongboxes. They learned the amount of dynamite needed to breach secure compartments without destroying the valuable contents inside.

In some cases, they would place charges on the tracks to derail trains, forcing them to stop. This allowed robbers easy access to cargo and passengers without much resistance.

Using dynamite was risky but proved to be an effective method for robbing high-value payloads, like gold and cash.

The Art of the Moving Train Robbery

Robbing a moving train required precise planning and timing. Gangs would board the train by jumping from horseback, or sometimes from a moving vehicle.

Once onboard, they would neutralize train personnel quickly to prevent any alarms from being raised. Their goal was to take control of the locomotive and slow or stop the train at a predetermined spot where other gang members waited.

Combining speed and element of surprise, they could rob passengers and cargo before making a swift exit.

Use of Diversion and Deception

Diversion was a common tactic where one group would create a distraction, like setting a small fire or engaging local law enforcement, to draw attention away from the real target.

Another method involved dressing as officials or workers, gaining access to the train without raising suspicion. They used fake orders or signals to confuse train operators, leading them into an ambush.

Such deceptive tactics minimized resistance and increased their chances of a successful heist. Some even manipulated train schedules and routes to ensure they struck at the most opportune moment.