Train robbery
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Train robbery was a crime that occurred mainly in the middle-to-late 19th century.
In a train robbery, the first goal was to steal any money being delivered as cargo. Trains carrying payroll shipments were, for this reason, a major target. These shipments would be guarded by an expressman whose duty it was to protect the cargo of the "express car". Expressmen, conductors, and other personnel took enormous pride in their duty and had no problem with risking their lives for a shipment. Bandits would rely on the expressman to open the safe and provide the goods. Without the combination, it was almost impossible to break into safes. The invention of dynamite made it much easier to break into safes and rob trains, however.
If the outlaw was unsatisfied with the goods, passengers of the train's carriages (generally unarmed) would be held at gunpoint and made to hand over any valuables they were carrying (usually jewelry or currency).
Contrary to the method romanticized by Hollywood, outlaws never jumped from horseback onto a moving train. Usually, they would either board the train and wait for a good time to initiate the heist, or they would stop / derail the train and then begin the holdup.
Famous train robbers include Bill Miner, Jesse James and Butch Cassidy. (more needed)