January 1924 began on a somber note when John’s father, Joseph “Joe” Warren Ashley was killed by a member of the sheriff’s posse at his moonshine camp while putting on his slippers one rainy night after hearing John’s dog, “Shine” barking close by. Joe was sixty-four years old. At this time, John was almost a year into being on the run again and was staying with his father while helping him in the distilling business. The moonshine still camp ambush was sparked by a train station robbery that took place two nights prior in Port Salerno (Then just called Salerno), only a few miles north. The report stated that $12.50 was taken from the railway office. The assumption was that the robbers were the Ashley boys. When Palm Beach County Sheriff Bob Baker caught wind of a train station robbery, he ordered a posse of 50 men to hunt John Ashley once again (John has been “hunted” since the killing of DeSoto Tiger in 1911). After a search mission for the boys and an hours long gun battle between the posse and the few locals at the newly discovered moonshine camp, John famously escaped west back into the Everglades, leaving his father and Sheriff Fred Baker dead and his girlfriend, Laura Upthegrove, splattered with lead shot. Laura survived but was quickly taken into custody along with 11 other Ashley family members who may have known something regarding John’s whereabouts.
John Ashley had previously escaped from Raiford Prison in North Florida for the third and final time in September of 1923. Another Everglades retreat wouldn’t be difficult. He was forced to live in the woods west of Hobe Sound away from potential capture in order to plan an escape out of Florida. Remember, back then anything west of Dixie was called the Everglades. His brother William “Bill” Ashley came up from Miami to join John but Bill didn’t make it very far. Bill was captured around Hobe Sound. Captain Von Behren of the Florida National Guard issued more guns and ammunition to be sent to Hobe Sound to assist in the capture of John Ashley.
In the Spring of 1924, John Ashley appeared to pose such a threat to the local people of northern Palm Beach County that an actual machine gun was included in this order. From April 1924 until September 1924, John Ashley was hiding out in Port Salerno, securing enough provisions to last him six months at sea. Now we have to ask, where was he going and why?
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