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, known as”Queen of the Everglades,” who lived in Canal Point on the northeastern shore of Lake Okeechobee.
And like Bonnie and Clyde, Ashley and three of his cronies ended up dead in an explosion of gunfire.
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Laura Upthegrove and John Ashley were known as ‘king and queen of the Everglades.’
The gang would rob 40 banks of at least $1 million, pirate shipments of liquor in Florida and the Bahamas and nonchalantly gun down officers of the law. By the time John died, they’d killed three.
Their deaths on a wooden bridge over the St. Sebastian River on Nov. 1, 1924 — 100 years ago — put an end to the Ashley gang’s infamous career of crime. Four men, including John, were captured by law officers but then turned up dead.
An Indian River State College professor learned in the 1950s what really happened from a deputy who was there. She never told the tale until they all were dead.
More: County marks anniversary of 1924 deputy’s slaying
2 sheriffs from Palm Beach County went after the gang
Palm Beach County Sheriff Bob Baker who took down the Ashley gang.
The gang’s leader was John, a compelling figure with a glass eye. He and Palm Beach County Sheriff Bob Baker would form a personal grudge against each other.
John Ashley was born near Fort Myers in 1888. After his birth, the family moved to Gomez, a settlement near Hobe Sound.
The rest of the gang consisted of John’s father, Joe; his brothers, Bob, Ed and Frank; nephew, Hanford Mobley; Clarence Middleton; and a bank robber from Chicago, Kid Lowe. Joe himself was a former law officer who moved into bootlegging.
John Ashley in 1917.
The first sheriff of Palm Beach County, George Baker, took office when the county was formed in 1909. He was the first law officer to order John Ashley jailed.
Baker’s son, Bob, who took over when George died, would help take down the gang.
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A Seminole chieftain’s son is killed
John Ashley began his life of crime at the tender age of 19. He was accused in 1912 of fatally shooting DeSoto Tiger, son of a Seminole chieftain. Tiger’s body was found during dredging of the New River Canal in Fort Lauderdale. He’d been shot in the back.
Palm Beach County’s first sheriff, George Baker
John Ashley was the last person Tiger was seen with, in the back of a canoe with otter pelts. The person who bought the pelts had a receipt signed “J. Ashley.”
George Baker would order John’s arrest, but John escaped to New Orleans. Finally, he surrendered in 1914. Deputy Bob Baker escorted him to the Palm Beach County Jail where Joe Ashley had a plate of food for his son. The deputy asked John to hold the plate while he unlocked the jail. John threw down the plate to escape again and disappeared into the Everglades.
The gang robbed banks and rail offices, which carried a lot of cash at the time. One robbery, of the Bank of Stuart in February 1915, was successful yet scarred John. They pulled in more than $4,200 but on the way out, Kid Lowe’s gunshot ricocheted off the back window frame of their car and hit John in the jaw. It also traveled through his eye. That’s how he got his glass eye.
By 1923, Ashley had a “to the death” feud with Sheriff Bob Baker. Ashley during a robbery sent Baker a bullet “with your name on it,’ and Baker sent word back that one day he’d wear Ashley’s glass eye as a watch fob.
How the gang killed 3 law officers
Clockwise starting at top; John Ashley, Hanford Mobley, Clarence Middleton, Roy “Young” Matthews, Ray Lynn. Center: John Ashley and his sweetheart Laura Upthegrove, King and Queen of the Everglades.St
Bob Ashley attempted to free his brother John from jail in February 1915. He shot and killed Deputy Sheriff Wilber W. Hendrickson at his front door next to the jail so Bob could get the keys.
During his getaway, Bob confronted Miami Police Officer John Rhinehart “Bob” Riblet and a gun battle ensued. Both died. Riblet was the first Miami police officer to die and the city was devastated.
John surrendered through his lawyers, stood trial and was sentenced to 17½ years in prison. He then escaped while working on a road crew in 1918.
In early January 1924, Sheriff Bob Baker led a posse that attacked the Ashley Gang’s camp site near Gomez. During the firefight, Joe Ashley was shot in the head while tying his shoes. John Ashley saw his father die and in turn, fatally shot Deputy Fred Baker, Bob Baker’s cousin.
At a bank robbery in September 1924, John Ashley gave a bullet to a teller and said, “You give that to Sheriff Bob and tell him I got another one just like it waitin’ for him if he’s man enough to come and get it.”
The bloody end on a bridge over the Indian River
Stuart Police Chief Oren Padgett in 1922. Padgett spotted an Ashley family member on the day of the ambush.
Stuart Police Chief Oren Padgett spotted Ashley’s brother-in-law on Nov. 1, 1924 at a Stuart grocery store. He learned from a source that the gang was headed to Jacksonville that night.
Though Palm Beach County Sheriff Bob Baker was John Ashley’s nemesis, he wasn’t present when officers caught Ashley and three others on the St. Sebastian Bridge. But he sent his own deputies to help. Together with St. Lucie Sheriff J.R. Merritt and his deputies, they caught the outlaws.
Captured were John Ashley, Hanford Mobley, Ray “Shorty” Lynn and John Middleton. The four wouldn’t be seen alive again.
Clarence Middelton, part of the Ashley gang, which was begun and led by John Ashley and his nephew Hanford Mobley, robbed central Florida banks, bootlegged, and usually escaped any jail. Four members of the gang were caught and shot on the Sebastian River Bridge on Nov. 1, 1924.
The bodies are taken to Fort Pierce and displayed on the grass in front of a mortuary.
But in the 1950s, when all but one of the deputies who had been on the bridge had died, that last one 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.
Eliot Kleinberg is a former Palm Beach Post reporter. Holly Baltz is the Investigations Editor at The Post. You can reach her at [email protected].
This article originally appeared on Palm Beach Post: Ashley gang terrorized people in the 1920s in Florida
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Publish date : 2024-11-14 05:56:00
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