From 1915 to 1924, John Ashley and his moll Laura Upthegrove led their gang in over 40 bank robberies, stealing more than $1 million & hijacking so many shipments of illegal whiskey being smuggled from the Bahamas that rum-running virtually ceased along the Florida Coast.
Among Florida Crackers, they were considered folk heroes often compared to Jesse James and his gang, as they represented a symbol of resistance to bankers, lawmen, and wealthy landowners.
John was the son of a poor Florida woodsman and spent much of his youth in the Everglades. Like his father, he became a skilled trapper and alligator hunter, and learned how to survive in the Glades.
In 1911, a dredging crew working near Lake Okeechobee found the body of Seminole trapper Desoto Tiger. John soon came under suspicion as the two were last seen in a canoe together with $1200 worth of otter hides to sell in Miami. Authorities attempted to arrest John, but were ambushed and disarmed by his brother, Bob, and told not to come back.
Despite overwhelming evidence, John was not convicted for the murder of DeSoto Tiger. When the Seminole Nation raised protest over the murder & the US government threatened to intervene, John fled to New Orleans before returning to Florida around 1914.
He surrendered himself to authorities but soon decided to escape, breaking away from his guard, running out an unlocked door, and climbing a 10 ft fence to freedom.
He and his brothers then became outlaws and formed a criminal gang. He began a relationship with Laura, who acted as their lookout, driving through secret backwoods trails without headlights to warn the gang when authorities were near.
During one robbery, John was shot in the jaw, injuring his eye. When he sought medical attention, he was apprehended for the murder of DeSoto Tiger yet again. Laura would play a central role in the gang’s activities for the 2 years John was imprisoned before his escape from a road camp.
The gang would continue robbing banks, moonshining, and piracy until 1924, when John was killed in a shootout with authorities, possibly tipped off by Laura, who committed suicide in 1927.
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