John Ashley

John Ashley was the leader of a gang called the Ashley Boys that terrorized Florida in the early 1900's. The gang was responsible for bootlegging, murder, and bank robberies.

One of the first acts of the Ashley Boys was a bank heist in Stuart Florida in 1915. Following the holdup, Ashley was accidentally shot in the face by one of his own men, Kid Lowe. The bullet entered his jaw, blinded his left eye, and later caused him to wear a glass eye. This incident slowed the gang down, and they were soon captured by local Sheriff George Baker. This was not the first run-in between Baker and Ashley. In 1911, Ashley was accused of murder, and the Sheriff sent two deputies to bring him in. Ashley set up an ambush with his brother, and the men drove the officers away with a message that if more deputies came looking for him, they would get seriously hurt. Ashley left the state, but returned in 1914 and turned himself in. Following a mistrial, authorities attempted to move him to Miami for a second criminal hearing, but Ashley escaped and began the formation of his gang.

Ashley was once again taken into custody by Sheriff Baker, largely because of the accidental bullet wound. He then faced two trials, one for the 1911 murder charge and another for the bank job. He was acquitted of the killing and spent a short time in prison for the robbery. Before long, he was moved to a road camp from which he escaped in 1918 to rejoin his gang. Following the declaration of Prohibition in 1920, the Ashley Boys took up bootlegging and rum-running.

By 1921, Ashley was back in prison after being caught with a shipment of illegal alcohol. While he was incarcerated, the Ashley Boys continued to operate and even held up the Stuart bank a second time. It wasn't long before Ashley escaped again and met up with the members of his gang, who were being pursued by the new Sheriff, George Baker's son, Robert.

The gang pulled off several more bank robberies, and Ashley developed a habit of leaving a gun with one bullet in the chamber at each crime scene to be delivered to Robert Baker. Ashley did this after a bank robbery in Pompano, and Baker swore he would bring Ashley to justice and claim his glass eye.

Towards the end of 1924, an informant notified Baker that the Ashley Boys would be coming to town to kill the Sheriff and his deputies. They set up an ambush and managed to surround the gang with an armed posse. Every member of the gang was shot dead that night. Whether they were killed while attempting to escape or while handcuffed and in custody remains uncertain, but the Sheriff and his men were cleared of any wrongdoing.

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