John Ashley terrorized Florida in the early 1900s as the leader of the Ashley Boys gang. Together, they engaged in bootlegging, bank robberies, and murder.
One of the Ashley Boys’ first crimes was a bank heist in Stuart, Florida in 1915. In the confusion following the holdup, Kid Lowe, one of the Ashley Boys, accidentally shot John Ashley in the face. The bullet entered through his jaw and destroyed his left eye, forcing him to wear a glass eye for the rest of his life. This incident slowed the gang down, and local Sheriff George Baker soon captured the Boys. This was not the first run-in between Baker and Ashley. In 1911, authorities accused Ashley of Seminole trapper Desoto Tiger’s murder, and the Sheriff sent two deputies to bring him in. Ashley and his brother set up an ambush and drove the officers away, with the warning that if more deputies came looking for him, they would get seriously hurt. Ashley then 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.
In 1915 Sheriff Baker brought Ashley into custody once again. He had tracked down and captured Ashley while Ashley had been seeking medical attention for his bullet wound. At this point, Ashley faced two trials, one for the 1911 murder charge and another for the 1915 bank robbery. The court acquitted him of the killing and he only spent a short time in prison for the robbery. Before long, Ashley transferred to a road camp. In 1918, he escaped once again and rejoined his gang. Following the 1920 establishment of Prohibition, the Ashley Boys began bootlegging and rum-running.
By 1921, Ashley had returned to 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. Ashley soon escaped for a third time and met up with the members of his gang, who were being pursued by the new sheriff, George Baker’s son, Robert.
Rejoined by Ashley, the gang continued to execute bank robberies. Meanwhile, Ashley developed a new signature to taunt Robert Baker: at each crime scene he would leave a gun with one bullet in the chamber. Baker, infuriated, swore he would bring Ashley to justice and claim his glass eye for himself.
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. Baker set up an ambush and managed to surround the gang with an armed posse. Every member of the gang died that night. Whether Baker and his team killed the Ashley Boys while they were attempting to escape or while they were handcuffed and in custody remains uncertain, but the sheriff and his men never faced charges.