A century and a half ago today, a pair of Indiana brothers developed a new American artform: the train robbery. On October 6, 1866, the Library of Congress writes that John and Simeon "Sim" Reno got on an Ohio & Mississippi Railroad passenger train near Seymour, a city in Jackson County, Indiana. Soon the pair moved down the train to a car owned by the Adams Express Company, a firm that delivered packages, documents and bank drafts (in fact, it is one of the oldest U.S. companies still in existence, though it now sells equity funds).

Wearing masks, the brothers entered the car, pointing their guns at Adam’s employee Elem Miller and demanded he open the company safes. He only had access to the local safe, so the brothers grabbed the loot from that one and tossed another larger safe off the train. They signaled for the train to stop and fled into the darkness before the conductor continued on, unaware that a robbery had just taken place. The brothers got away with an estimated $10,000 in gold coins and $33 in bank notes. They were never able to crack the safe they threw off the train.

The robbery wasn’t their first rodeo. William Bell, writing for Wild West magazine, reports that the Reno brothers and their gang were the scourge of southern Indiana both before and after the Civil War. In the early 1850s, almost every building in the town of Seymour was burned down, some several times over. It was rumored that some of the Reno boys—Frank, John, Simeon and William—were the arsonists, but it was never proven. (Clinton, the fifth brother, got the nickname "Honest Clint" because he wasn't a member of the gang, though he was not exactly a Boy Scout himself.) During the Civil War, some of the brothers served in volunteer guards, but at least Frank and John served as bounty jumpers. Men called up through the draft would pay them to take their place. After enlisting, the Reno boys would desert their regiment, then find another bounty and repeat the process.

Near the end of the Civil War, John and Frank returned home, bringing with them a motley crew of bounty jumpers, counterfeiters and other outlaws. The area began suffering post office robberies, home invasions, and the murder of anyone who tried to rat out what had become known as the Reno Gang. In that atmosphere, they hatched their train robbery scheme.

Little did they know, the Adams Company was under the protection of the Pinkerton Detective Agency, which quickly discovered Frank and Sim’s involvement in the robbery. The two were arrested, but the only eye witness to the crime was murdered while the brothers were out on bail awaiting trial and the case fell apart.

The train robbery helped establish the reputation of the Pinkerton Agency, but it also unleashed long, deadly era of train robberies in the U.S., writes History.com. As the American West began to boom in the 1870s and 1880s, trains carrying cash and precious minerals became prime targets, especially in wide open spaces where bandits could set up road blocks for the trains and easily slip into hiding. Some of the United States most famous criminals, the likes of the Farrington Brothers in Kentucky, Jesse James in Missouri and Butch Cassidy’s Wild Bunch in Wyoming, focused on trains.

But over time, the railroads wised up. Many added massive, unmovable safes to their trains and often hired armed guards. Some even added cars with armed men and horses who could be deployed to chase down any bandits who robbed the train.

Things didn’t end well for the Renos. In May, 1868, Frank, William and Sim (John was in prison in Missouri) stopped a train in Marshfield, Indiana, south of Seymour. They savagely beat a train guard before getting away with $96,000 in cash, gold and bonds. The three were picked up by law enforcement and thrown in jail. But after the train guard died from his injuries in December, a vigilante mob broke the Renos out of jail and hung them from a tree.