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South Florida's most wily gangster: John Ashley

John Ashley confounded deputies from Stuart to Miami - until he met an end that rivaled Bonnie and Clyde's.

This story was originally published March 13, 1997

 If he were alive today, John Ashley might be just another street thug.
    Instead, the tall man with the glass eye became South Florida's most romanticized gangster.
    Long before Bonnie Parker and Clyde Barrow became America's great anti-heroes, Ashley and his ragtag gang enthralled and infuriated Boom-era Florida with their robbing, hijacking, rum running and even murder.
    Ashley even had a "Bonnie" of his own - Laura Upthegrove, "Queen of the Everglades."
    And like Bonnie and Clyde, Ashley and three of his cronies ended up dead in an explosion of gunfire.
    Their deaths on a wooden bridge over the St. Sebastian River in 1924 put an infamous end to the Ashley gang's infamous career of crime.
    Deputies said the gang was shot because they tried to escape. But many believed the Ashleys were assassinated by lawmen tired of being humiliated from Stuart to Miami by the gangsters.
    Now, Ada Coats Williams, a retired teacher of creative writing at Fort Pierce's Indian River Community College, has completed Florida's Ashley Gang, the first book on the Ashleys since 1928's The Notorious Ashley Gang.
    Williams was a good candidate to write it: She was there.
    "My father knew all these people," recalled Williams, whose family setted the area in the 1870s.
    Williams had gotten the real story about the Ashley gang's shooting in the 1950s from a retired deputy who'd been on the bridge that night. His one condition: she keep it secret until after all the deputies involved had died.
    Williams kept her promise.
    "It was the last time someone could give the story, documented," she said.
    Most notorious antics
    In 1911, John Ashley robbed some Seminole Indians of their furs and killed the son of a Seminole chief.
    By 1923, Ashley had a "to the death" feud with local Sheriff Bob Baker. Ashley would send Baker bullets "with your name on it,' and Baker sent word back that one day he'd wear Ashley's glass eye as a watch fob.
    In 1924, Ashley's handsome nephew dressed as a woman to rob the Stuart Bank.
    The Ashley Gang saga
    March 19, 1888: John Ashley is born near Fort Myers.
    1. 1911: The Ashleys move to West Palm Beach, then to Gomez, near Hobe Sound.
    2. Dec. 29, 1911: John Ashley murders DeSoto Tiger, the son of Tommy Tiger, head of the Cow Creek Seminoles. Tiger's body is found in a canal northwest of Fort Lauderdale. (B)
    When Palm Beach County Sheriff George Baker sends two deputies to Ashley's home, Ashley escapes arrest and warns the deputies: "Tell Baker not to send any more chicken-hearted men with rifles or they are apt to get hurt."
    He surrenders two years later but escapes after the jury in the murder trial deadlocks.
    Early February 1915: Ashley, his father and his nephew, Hanford Mobley, try to rob a Florida East Coast Railway train, but a woman's screams stop them, and the gang flees a mile south of Stuart.
    3. Feb. 23, 1915: John, his brother Bob and Kid Lowe rob the Stuart Bank. (C)
    Lowe fires a shot that shatters John Ashley's jaw and rests against his left eye. Sheriff Baker catches only John Ashley, who refuses surgery to remove the bullet. He is later fitted with a glass eye.
    4. June 2, 1915: Shootout at Dade County Jail. (D) Trying to spring John Ashley from jail, brother Bob knocks on the door of Deputy Sheriff Wilber Hendrickson's home, next to the jail.
    "Are you Hendrickson?" Bob asks, then fires his rifle.
    Bob takes the keys from the dying Hendrickson. But the commotion alerts Hendrickson's wife. Bob panics, drops the keys and jumps into a passing car.
    After a few blocks, a Miami police officer catches up with Bob. Both fire their guns. Both die.
    John Ashley insists he didn't know of the escape attempt.
    Summer 1918: Ashley escapes from road camp and spends three years operating stills in northern Palm Beach County and running rum from the Bahamas.
    October 1921: John's brothers, Ed and Frank Ashley, disappear while returning from the Bahamas with rum. (E)
    5. November 1923: Ashley and his gang steal a cab and rob the Pompano Bank. (F) Ashley leaves the cabbie a bullet and dares Palm Beach County Sheriff Bob Baker, George Baker's son, to look for him in the Everglades.
    6. February 1924: Sheriff Baker's posse opens fire at the Ashley camp in western Martin County. (G)
    Joe Ashley, John's father, is shot as he ties his shoes. John, seeing his father hit, kills deputy Fred Baker. The gang flees, and angry townspeople burn the Ashleys' camp and homes.
    September 1924: John Ashley's 19-year-old, slender nephew, Hanford Mobley, dresses in a white blouse, a long black skirt, a hat and a veil. "She" robs the Stuart Bank.
    7. Nov. 1, 1924, shootout at the St. Sebastian Bridge: Palm Beach County Sheriff Bob Baker gets a tip that the Ashleys plan to head to Jacksonville, then return and kill him. He alerts his St. Lucie counterpart, J.R. Merritt, that Ashley might be heading his way.
    Baker sends up four deputies, who join Merritt and two of his men.
    At about 10:45 p.m., a red lantern is swinging from a chain strung across the wooden bridge at St. Sebastian River. (H)
    Two youngsters from Sebastian pull up. Merritt steps from the bushes and tells them to drive on. Behind them, the Ford bearing Ashley and his gang - Hanford Mobley, Ray "Shorty" Lynn and John Middleton - comes to a stop. The lawmen surround it.
    The two young men turn around, and their headlights fall on four men standing handcuffed on the bridge. They race to Sebastian to tell everyone the Ashleys had been captured. Before they got there, the gang members are dead.
    The bodies are taken to Fort Pierce and displayed on the grass in front of a mortuary. In the morning, they are laid out on a sidewalk for gawkers.
    The deputies' official story: The gang had raised their hands, but when Ashley saw the glint of the lantern on handcuffs, his phobia caused him to drop his hands and shout, "Shoot boys. They'll never put those things on me."
    A judge ruled the shootings justifiable. The deputies took an oath never to speak of them again.
    But in the 1950s, when all but one of the deputies who had been on the bridge had died, that last deputy confided to Ada Williams his story:
    Convinced that no jail could hold the gang, the deputies had determined to finish them off.
    They cuffed John Ashley and made him raise his hands. As they cuffed the others, Ashley began to drop his hands. A deputy shot him dead. The others fired wildly and the rest of the gang was killed.
    The deputy said he scooped out Ashley's glass eye for Sheriff Baker.
    When he found out later that the eye had been returned to Ashley's family, the deputy said he had one regret: He should have crushed it with his heel.
    Outlaws of the Everglades
    Big John and Little Laura
    John Ashley (1888-1924), leader of the Ashley gang
    Young John was an expert trapper in the then-expansive Everglades - and a crack shot. Friends said he could behead a quail with a single shot from 40 feet while riding a wagon.
    "I never saw a more mannerly or nicer boy in my life," a relative said. "He always came in with a smile and a pleasant word for all."
    Others told of acts of kindness: leaving money or food for needy people, ditching a bank robbery after learning the bank president was a childhood playmate, disarming but sparing a man sent to kill them and sending him off with a $5 bill.
    But Ashley and his gang also made a career of bank robberies, kidnappings, theft, hijacking, rum-running, moonshining, even murder.
    Laura Upthegrove, "Queen of the Everglades" and John Ashley's girlfriend
    Laura was a member of the Upthegrove family that settled along the northeast shore of Lake Okeechobee. Upthegrove Beach, north of Port Mayaca, is named for them.
    One report described her as "a large woman with dark hair, a deep suntan, and wore a .38-caliber revolver strapped to her waist." She allegedly helped plan crimes.
    Devastated by Ashley's death in 1924, she later ran a small store in Canal Point. During an argument with a customer over change, she grabbed a bottle of cleaning fluid from a shelf and drank it; she was dead in minutes.
    Valda Padgett, Laura's sister, still lives in Vero Beach, but refuses to speak on the record - except to say virtually everything written about her sister is a lie.
    The Ashley Family
    Joe Ashley (1861-1924), John's father
    In 1904, he brought his wife and five sons from Florida's Gulf Coast to Pompano Beach, then moved to West Palm Beach in 1911, and then to Gomez, near Hobe Sound.
    The Ashleys were like many hard-scrabble families who farmed, hunted and did odd jobs in frontier South Florida. Joe got a job as a wood chopper for the railroad. Later, he took part in his son's exploits. In the 1924 raid at the Ashley gang's western Martin County camp and moonshine operation, he was killed as he tied his shoes.
    Leugenia Ashley (1862-1946), John's mother
    She buried a husband and four sons, all victims of crime and violence.
    John Ashley's brothers Bob (1894-1915), Ed (1880-1921) and Frank (1900-1921) died committing crimes. Bill Ashley (1883-1940) was the only Ashley brother who survived the family business. He settled in Pompano Beach.

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