The London and Madrid bombings are the most recent examples of attacks on rail and transit systems around the world. Although they represent a frightening escalation, these attacks are only the latest in a criminal history which dates back to the mid-19th century, when railroads in the United States and elsewhere first became attractive targets. This is the first article in our new series, “Crime in Motion,” where we will explore the history of train and transit crimes, look at some high-profile cases in depth, examine the issues of prevention and response, and discuss security concerns for the future.
THE THREE FIRST TRAIN ROBBERIES
It was a quiet Friday in May time. Less than a month earlier, General Robert E. Lee had surrendered to Ulysses S. Grant at Appomattox, officially ending the Civil War. One by one, Confederate armies were surrendering. Just the day before, on May 4, General Richard Taylor, in charge of Confederate forces in Alabama, Louisiana and Mississippi, ended his war by surrendering to Union General E.R.S. Canby. On that day, the nation was still reeling from the assassination of President Abraham Lincoln.
Railroads had played an important part in the War Between the States. Blowing up a key rail line, or capturing a train, gave advantage to one or the other side. While the North and South fought, the nation hadn’t yet been linked from east to west by railroad: that wouldn’t come until 1869, four years after the Civil War ended. Railroads, in fact, were still very new: it was only 1830 when the first steam-powered rail line opened in the U.S. That was the Baltimore & Ohio Railroad, with the now-famous “Tom Thumb” locomotive pulling a single open car at 18 miles per hour from Baltimore to Ellicott’s Mills, Md.
But it was a different railroad with Ohio in its name that was scheduled to enter history on that Friday, May 5, 1865. According to accounts, about a dozen men ripped up the tracks of the Ohio & Mississippi Railroad a couple of miles west of the village of North Bend, Ohio, today a suburb of Cincinnati. They derailed a westbound train with the aim of robbing it, committing what is sometimes cited as the nation’s first train robbery.
No one was injured in the derailment, but the robbers took cash and jewelry at gunpoint from more than 100 passengers. Then, they blew open the safes of the Adams Express Co. that were reported to be carrying thousands of dollars in government bonds. The robbers fled across the Ohio River and, despite being hunted by U.S. troops, were never found. Their identity is unknown to this day.
However, many sources cite a different train robbery, which occurred more than a year later, as the first in the United States. These robbers simply seem to have had better P.R.
They were the Reno Brothers, of Indiana. Local lore holds that they began their criminal career with a seven-year streak of arson fires in the town of Rockford during the 1850s. After the War, they turned to burglary, murder and any other crimes that interested them. But it was always money they were after.
They chose a Saturday. October 6, 1866 to be exact. And it was the ill-fated Ohio & Mississippi Railroad that was to fall victim to train robbery again.
At the town of Seymour, Indiana, three members of their gang, including two of the brothers, boarded an eastbound train. Meanwhile, the other two brothers, Frank and William Reno, along with other gang members, were waiting with horses some miles down the track. The three aboard the train made their way to the express car. They demanded the keys to the Adams Express safes from Elem Miller, in charge of the car, but his keys could open only one of the safes. Then, one of the robbers pulled the signal cord to instruct the engineer to stop the train. As it slowed, they pushed the unopened safe out the door and followed out themselves. One of the gang shouted, “All right” to the engineer, who sped away into the night unaware of what had happened.
The advent of the “trade of train robbery,” as screenwriter, author and presidential speechwriter Charles Michelson has called it, seems to have arisen from the confluence of three events. First, of course, was the rise of railroads in the U.S. as important conveyors of people and goods. Second, the end of the Civil War left adrift a large number of hardened men looking for excitement and money. Third, the railway express business presented an enticing target.
Before railroads, goods and other valuables had to travel by horse, stagecoach or wagon. Trains made their transport faster, more reliable and safer. Railroads also created more such shipments: they needed to move payrolls for their men and freight to newly-settled towns.
The U.S. Postal Service was not in the business of sending anything larger than a letter back then; parcel post didn’t exist in the 19th century. But, if you take a look in your wallet, you will likely find a direct link to that time. American Express began as a railway express business. Established in 1850, it was one of a number of express companies formed to serve the small package and document delivery business. They were the FedEx’s of the mid-to-late 1800s.
A rival, Alvin Adams, had begun his business in 1840, and as the railroads grew, so did his fortunes. In 1854, the Adams Express Company was incorporated, bringing in a number of partners, but with Alvin Adams as president. The company expanded from its base in the Northeast to the South, Southwest and West Coast. It became, along with American Express and Wells Fargo, one of the big three.
The lure of high-value shipments – often cash, or jewelry and securities that could be readily transformed to cash – initiated the era of the great train robberies.
But wait. There is yet a third “first train robbery” which occurred between the other two “first train robberies.” This one isn’t cited anywhere as the first train robbery, but is described in a family memoir by Margaret Pinkerton Fitchett, a descendant of the founders of the Pinkerton Agency.
This security and detective firm, which dates to 1842, largely owed its success to the growing popularity of train robbery in the post-Civil War period. Fitchett asserts, “In fact, it was the railroad which eventually underwrote the whole concept of the Pinkerton business and we find all the main lines in the region forking out substantial annual retainers.”
The Pinkertons’ fame grew out of the successful investigation of a sensational robbery along the New York – Boston line that netted the thieves more than $700,000 in cash, bonds and jewelry.
It may have been sensational, but it was poorly planned and ineptly executed. And once again, the Adams Express Company was the victim.
John Grady, a brakeman for the New York & New Haven Railroad, had observed that a particular Adams guard named Moore was noticeably lazy in the performance of his duties. So, when Grady learned that this guard had been put in charge of a big shipment on the night of January 6, 1866, the amateur robber enlisted the aid of three other amateurs to heist the valuables from the Adams’ safes.
Moore later admitted to Pinkerton investigators that he had checked the padlocks on the door to the express car only once, at Bridgeport. Had he been more diligent, he would have noticed that further up the line, Grady’s gang had pried off the padlock and were inside the car filling two suitcases with the contents of the safes. They later jumped off the train with the loot.
The Pinkerton Agency, having been immediately hired by Edward Sanford, president of The Adams Express Company, immediately sent investigators to check along the train’s route. They found one bag containing $5,000 in gold coins hidden in the bushes. A local innkeeper identified Grady as having been in the area that night. While he was being sought, an old man named Tristam became suspect and was trailed to his apartment in New York City. “When Pinkertons raided the place, they found the Adams Express bags with nearly one hundred and fourteen thousand dollars still intact,” according to Fitchett’s memoirs. “Caught in the act, the old fellow had no recourse but to tell all he knew. All the gang were successfully rounded up and one, turning state’s evidence, explained how the job had been done.”
Thus, we have three first train robberies. The first, by date, was committed by criminals who were never identified, so it suffers from a lack of publicity. The first large train robbery, because it was committed by amateurs who were quickly caught, was of publicity interest only to the Pinkerton Agency. The robbery most often cited as the first benefits from having been committed by the Reno brothers, who gained fame by terrorizing Indiana both before and after the Civil War.
As the wave of train robberies grew in the late 1860s and 1870s, railroads and express companies began placing guards and detectives aboard their trains. The Pinkerton Agency was well positioned to benefit from this.
Robert Pinkerton had first dubbed his agents as “railroad detectives” as early as 1843, helping the fledgling industry respond to petty thefts, burglaries and general lawlessness. His brother Allan became his business partner in 1850. They had developed an association with the Adams Express Company dating from 1858, when they were hired to solve the mystery of missing money sent in locked strongboxes from Columbus, Georgia to Montgomery, Alabama by rail. Some $50,000 was lost in a series of incidents in which the boxes weren’t opened and the locks weren’t tampered with. Through creative sleuthing, the Pinkertons discovered that the Columbus station agent, John Maroney, was responsible. Agency detectives found much of the money – some $39,000 – in a trunk hidden in the Maroneys’ basement.
Hold on now. This crime took place in 1858, which, by a seven-year margin, makes the Maroney caper the first train robbery in U.S. history, although it is never cited as such. Apparently, he had the worst press agent of all.




