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Florida newspapers in the 1920s compared outlaw John Ashley to Jesse James.
On more than one occasion, however, the gang’s escapades seemed like a scene from a Quentin Tarantino film.
There was the 1915 raid on a bank in Stuart, for example. The gang, including Ashley’s three brothers and Chicago tough “Kid” Lowe, didn’t have much going in the getaway department. After snatching $4,500, Kid Lowe shouted at the bank’s customers: “All right, which one of you can drive an automobile? It’s either drive us out of here or get shot.’’
One patron agreed to drive the getaway car.
According to a Sun-Sentinel account: “As the Ashley gang sped away, four lawmen fired guns in a futile attempt to stop them. Lowe, sitting in the front seat, turned and fired back. One of his bullets struck the car’s rear window frame and ricocheted into John Ashley’s left eye.”
While the rest of the gang got away clean, Ashley was captured three hours later at a nearby hideout. “He lay on a bloodstained bed of pine needles, too wracked by pain to resist.” After that, he was a one-eyed bandit with a glass eye.
The arrest for the robbery, though, took a back seat to a more serious crime. Ashley was sent to Miami to stand trial for the murder of DeSoto Tiger, son of a Seminole chieftain.
The young trader was killed in 1911, becoming Ashley’s first documented crime since his father Joe had moved the family to Pompano Beach six years earlier.
In short order, almost the entire Ashley family became nothing but trouble. Along the way Ashley brought his girlfriend Laura Upthegrove into the crime cult, and they called themselves “King and Queen of the Everglades.” That’s where their hideouts and moonshine stills were located. Upthegrove was said to be the mastermind of a slew of bank robberies, rum-running and kidnapping crimes, often casing the joints herself when necessary.
While the Stuart robbery was slapdash, others were cruelly efficient. All told, the Ashley Gang racked up what would be $12 million in today’s money before their careers were ended.
After the Stuart fiasco, John was held in Miami because he sold 84 otter skins stolen from DeSoto Tiger to the Girtman Brothers trading post there.
The body of DeSoto Tiger was found floating in a slough in today’s northwest Broward. The Girtman Brothers said they bought the otter skins from a “husky young fella whose signature on the receipt was J. Ashley.”
With John Ashley finally in jail for the crime, brother Bob – the most violent of John’s three brothers in the gang – was plotting. He finally busted into the Dade County Jail and shot the jailer. In a shootout, Bob killed another officer, took a bullet in the stomach and died.
John remained in jail then but later escaped from a road crew. In the ensuing years, he and Laura eluded the police up and down the state. But two of his brothers disappeared on a rum-running excursion to the Bahamas and father Joe died in a raid of his moonshine camp.
The end for John came in 1924. Palm Beach County Sheriff Bob Baker claimed at the time that John and three gang members were killed trying to escape. But author Ada Coats Williams, a retired teacher of creative writing at Fort Pierce’s Indian River Community College, has another take on that story.
“My father knew all these people,” recalled Williams to the Palm Beach Post. As told in her 2016 book, Florida’s Ashley Gang, a retired deputy who’d been on the scene that night came clean before he died.
The fatal encounter took place on a wooden bridge over the St. Sebastian River. Sheriff Baker got a tip that the gang was headed toward Jacksonville. He alerted his St. Lucie counterpart that Ashley might be heading his way. Baker sent up four deputies, and seven officers were ready to ambush the gang.
They set up a chain and a red lantern across the bridge at St. Sebastian River.
At around 10:45, the Ford bearing Ashley and his gang – Hanford Mobley, Ray “Shorty” Lynn and John Middleton – came to a stop. The lawmen surrounded it.
The deputies’ story then was that the gang had raised their hands, but when Ashley saw the glint of the lantern on handcuffs, he dropped his hands and shouted, “Shoot boys. They’ll never put those things on me.” All four died in the gunfight.
But Wlliams’ source says they cuffed John Ashley and made him raise his hands. As they began to cuff the others, Ashley began to drop his hands.
A deputy shot and killed Ashley. The others started to fire but were mowed down by the cops. No way were the police going to let them go again, according to Williams.
The bodies were taken to Fort Pierce and the next morning they were laid out on a sidewalk for gawkers.