I’d like to tell you a story of a train heist gone wrong, of a tough gang of thieves who didn’t quite pull off the job. And they didn’t get away either. But the men reporters called the Freedom Gang still have a story I think you’ll want to hear.
It was winter, 1901. Jesse James had been dead for nearly 20 years and Butch Cassidy and the Sundance Kid fled to South America earlier that year. More sophisticated law enforcement and secure forms of currency like traveler’s checks were making train robberies harder to pull off and even harder for bandits to get away. But the risks weren’t enough to stop the Freedom Gang from going after a safe full of cash, guarded by a lone engineer at a quiet Pennsylvania station.
The Freedom Gang was led by William O’Brien, a mustachioed Canadian who went by many names. Some called him Wolf or Little Joe or even Ralph Walhopper; he seemed to have a different name for each robbery he had pulled in the past. O’Brien was what the police called a “yegg man,” a burglar specializing in safe cracking. A printer by trade, he had a $100 price on his head for pulling off a string of bank robberies in Michigan. Moving east, he set his sights on the small town banks and unguarded railroad stations near the Pennsylvania-Maryland border.
O’Brien arrived on the East Coast and didn’t waste any time recruiting a gang of fellow thieves. He found four men who worked for the Northern Central Railroad– they knew the area well and would be less suspicious hanging around NCR stations late at night. The quintet pulled off a few small robberies in Aberdeen, MD and York Haven, PA before they moved on their big target: The NCR Station in New Freedom.
New Freedom was a small town on the Mason Dixon Line, 40 miles north of Baltimore. Its rail station was the junction of the Northern Central and Stewartstown railroads and the gang knew that a large amount of money was usually stashed in the office safe.
They broke into the New Freedom station late on a Wednesday night. The lone engineer guarding the office was out inspecting the tracks when the burglars crept in and got to work on the safe. O’Brien drilled a hole in it and stuck a short fuse and nitroglycerine inside. The bomb should have blown the door easily but surprisingly failed. Detectives said it was because a wedge stuck in the door joint had broken off and too much air was allowed to get in. There was $5100 cash inside; so close but just out of reach. The gang tried twice but failed each time.
After the second attempt the engineer returned from his patrol and noticed a light in the building. As he walked down the station platform, he neared the door and peered through the window inside. To his surprise, there was no one there and he turned off the light.
A second later a hand reached out from the darkness and grabbed him. The muzzles of four revolvers flashed in his face and a chorus of voices demanded he give up his valuables. He pulled away and started to run but a blow to the head knocked him out cold. He woke up a few minutes later to see the thieves holding his watch and pocket book. The Freedom Gang took him back to the office, threatened him not to tell anyone what happened, and said to go home. And before he knew it, the thieves had disappeared into the night.
The engineer waited till the coast was clear and ran for the police. Within a few hours railroad detectives were called in. They got to work early the next morning.
There weren’t many clues at the scene of the crime, the thieves wore masks and the engineer couldn’t identify any of them. There were no other clues left behind near the safe or on the office. The Freedom Gang had gotten away clean…or so it seemed.
After making some inquiries in New Freedom, the detectives learned that several men had spent the night in a nearby hotel bar. When they ran out of beer money the men pawned a watch with the barkeep for a few pints of whiskey and left. As luck would have it, this was the engineer’s stolen watch from last night.
The chase was on. After more questioning the detectives learned that an NCR trackwalker had seen several men drinking in an open freight car earlier that morning. They raced over to the railyard, but it was too late. The car was empty, save for two whiskey bottles tossed on the floor. With police assistance, the rest of town and locals interviewed, but there were no more signs of the gang.
The detectives widened their search to a 10 mile circle around New Freedom. A thorough hunt led them to nearby Bentley Springs and by the end of the day to Parkton. Searching the surrounding woods, they found five men asleep by a campfire. It was O’Brien and the Freedom Gang.
They stole silently into camp and aimed a pistol at each man. The signal was given and the gang was woken up and ordered to surrender. Two men tried to pull their own guns out for a fight but realized they’d been had. The chase was over; the Freedom Gang caught.
They were taken to the police station in Baltimore and searched. O’Brien’s men carried revolvers, a bottle of nitroglycerine, a bar of soap, chisels, $10 in cash, and a ring of keys in many shapes and sizes. For all their planning and preparations, this was all they had to show for their tiny crime spree.
The Freedom Gang’s run on the wrong side of the law was over. A sturdy safe, back luck, and good detective work doomed the thieves to a quick capture. But even if they had gotten away, the gang would have been one of the last great outlaw gangs to threaten America’s trains and banks. Their way of life was almost dead.
Though there would be a few more high profile train and bank robberies after the Freedom Gang was caught, the golden age of the outlaw gangs was over. It was becoming much harder for a gang to burst into town, pull a heist, and get away clean. Changes in technology, forensic science, law enforcement practices, and lots of other factors had changed the criminal landscape forever.
The story of the Freedom Gang barely registered a blip in the newspapers. It was, after all, a failed crime attempted by a couple of second-rate thieves who were easily captured. But the gang’s story ends better than most of the great train and bank robberies of the day. Many train robbers were killed in shootouts with guards, on the run from the law, or were swiftly sentenced to death by the courts. The Freedom Gang was sentenced to just seven years and nine months in the Eastern State Penitentiary, and they even got out early when a judge commuted their sentence.
Another Century 
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