From deceptive gamblers to corrupt killers, the Wild West was the land of the lawless, and it attracted outlaws from all around. But, the criminals who reigned—whose wild antics ruled over the frontier—were the real bandits. With a laundry list of heists to compare, these daring exchanges top them all for a very specific reason.
First Train Heist in the West
Chicago, Rock Island, and the Pacific Train Heist Adair, Iowa | June 24, 1889
While the Reno Brothers were the first to rob a moving train in 1866, it was the James-Younger gang that brought it to the West. The gang, made up of Jesse and Frank James, Cole, Jim, and Tom Younger, Clell Miller, and Bill Caldwell, heard about a train passing through the area that was rumored to have $75,000 (equivalent to $1,896,018 today) aboard. The possibility of a big payday was too tempting for them to pass up, so they produced a plan and put it into motion. About half mile west of Adair, they disconnected the spikes of a rail, and waited for the train to do the rest. Once the train reached the loose rail, it moved it out of place and caused the train to head straight for a ditch, toppling on its side in the process. The crash killed an engineer, a fireman, and left many passengers injured.
Jesse and Frank climbed in and forced the guard to open the safe. To their disappointment, there was only $3,000 (equivalent to $75,840.75 today) worth of gold. They took the gold, what they could get from the passengers, and fled to Missouri. Though never caught, most members of the gang would go on to pay for their many crimes, whether through jail time or with their lives.
Most Mysterious
Clay County Savings Association Bank Heist Liberty, Missouri | February 3, 1866
A heist that today, still goes unsolved, is the curious case of the Clay County Savings Association. Taking place in broad daylight, 10-13 men dressed up as Union officials, and two of the members went inside the bank. After asking for change for $10, the two thieves held the clerk and the cashier at gunpoint, robbed the vault, and forced them inside of it. They fled to their horses, and joined the rest of the men, who had begun shooting on the streets. Tragically, the shots fired resulted in the death of a 19-year-old man named George Wymore, who was passing by.
The nameless outlaws got away with $60,000 (equivalent to $1,144,766 today). While the men’s identities were never uncovered, it was rumored that it was Jesse James’ first robbery.
Luckiest
Union Pacific Train Heist Big Springs, Nebraska | September 18, 1877
Many things could go wrong during heists, and many things did for the fearless outlaws that roamed the West. But, for the Black Hills gang, luck was on their side when they robbed a passenger and cargo train, near present-day Big Spring, Nebraska. During the night, the train stopped at a remote water station, giving outlaws Sam Bass, Joel Collins, Jack Davis, Tom Nixon, Bill Heffridge, and Jim Berry the perfect opportunity to board. They took $1,300 and four gold watches from the safe that held the passengers’ valuables, but learned that the main safe was on a timer and locked until it reached its destination. After harassing the staff and threatening them at gunpoint, the gang realized they were telling the truth.
Right when they had accepted the disappointing payout and were ready to bail, they spotted three wooden boxes by the safe. To their pleasant surprise, the boxes held $60,000 (equivalent to $1,733,502 today) worth of $20 gold pieces. There were no fatalities, but they took one hostage, who later escaped unharmed. Eight days after the robbery, Collins and Heffridge died by the hands of the law. Berry died in Mexico a month later, and Nixon fled to his home country of Canada. As for Bass and Davis, they headed south, and their reputation became that of legends.
Most Hollywood-Worthy
Union Pacific Overland Flyer Train Heist Wilcox, Wyoming on June 2, 1899
Cue the daring jump off a moving train and the colossal explosions. The Wild Bunch gang brought the works when they came up with the elaborate plan for their 1899 heist. Using warning lights to flag down the train, the gang then climbed aboard, guns loaded, and overtook the first engine. Next, they disconnected it from the second part of the train. Using explosives, they blew up a bridge so the rest of the train couldn’t get through once they passed over it. The Wild Bunch fled to the horses they had hidden close by, getting away with $50,000 (equivalent to $1,827,487 today) worth of loot.
There was no blood shed during the over-the-top robbery, and the criminals never received any punishment for the heist. However, the life of crime did ultimately catch up with every single member, and all of them had died by 1912.
Most Epic Fail
First National Bank and Condon Bank Double Bank Heist Coffeyville, Kansas | October 5, 1892
Everything that could go wrong, did, for the Dalton gang on that fateful day in 1892. Whether Murphy’s Law was to blame or pure arrogance, the ambitious heist took a fatal turn for most of its members. Train robbers, Bob Dalton and Emmett Dalton, along with Grat Dalton, Dick Broadwell, and Bill Powers, set out to rob not one, but two banks, in the Dalton brother’s hometown. As the gang arrived, they tied their horses to a fence in an alley and split up—Bob and Emmett Dalton headed to the First National Bank and Grat, Dick, and Bill made their way to Condon Bank.
Instantly, the townspeople recognized the Dalton brothers and word of the outlaws’ presence began to spread. The streets began to fill and the people from the community surrounded the banks and started firing. Broadwell took a bullet in the arm through the window, and they all fled, making their way to the alley. Before reaching their horses, Bob and Grat were dead. Bill made it to his horse, but the vigilantes gunned him down from there. Emmett and Dick reached their horses, and Dick got away, but he had been hit several times, and ultimately succumbed to his wounds a few miles from town. Emmett turned back after he saw Bob go down from a gunshot. During his brave rescue attempt, the townspeople shot him, but he survived. Emmett spent over a decade in jail for his crimes. Once he served his time, he headed to Hollywood, and using his experiences as a Wild West outlaw, became a screenwriter for the Western films.