John Ashley had previously escaped capture when he was wanted for a 1911 murder. Eventually, he turned himself in, but the judicial circus that ensued resulted in a mistrial. During an attempt to move him to another venue, Ashley escaped, and left Florida for three years.
John Ashley wore a glass eye due to an accident during one of the Ashley Boys' first bank robberies, which occurred in 1915, shortly after his return to Florida. The gang was holding up a bank in Stuart, Florida, when John Ashley was accidentally shot by Kid Lowe, a member of the Ashley Boys. The bullet wound cost the gang time, allowing Sheriff Baker to catch up with them.
The Ashley Boys were tried for the robbery and John Ashley did a brief stint in prison for his role. He was acquitted, however, of the 1911 murder. He escaped from prison in 1918 and reformed the gang. The Ashley Boys continued their mischief and in 1921, John Ashley was sent to prison again for his bootlegging activities.
John Ashley managed to escape from prison yet again and resumed his criminal activities immediately. John Ashley was pursued by the new sheriff, the son of the first Sheriff Baker. John Ashley still had it out for the new Sheriff Baker, however, and during each of their many bank robberies, he took to leaving a gun loaded with a single bullet behind - for Sheriff Baker.
Eventually, an informant from the Ashley Boys tipped off Sheriff Baker about when the gang would be coming to town to visit John Ashley's father. An armed group surrounding the gang and every member of the Ashley Boys was killed. The Sheriff and his posse were cleared of any wrongdoing, although there were suspicions that the gang members were killed in police custody rather than while trying to escape the law yet again.
If you have been arrested or charged with a crime in Florida, contact the Tampa criminal defense lawyers at Musca Law.