John Hopkin Ashley (March 19, 1888 – November 1, 1924) was an American outlaw, bank robber, bootlegger, and occasional pirate active in southern Florida during the 1910s and 1920s. Between 1915 and 1924, the self-styled "King of the Everglades" or "Swamp Bandit" operated from various hideouts in the Florida Everglades. His gang robbed nearly $1 million from at least 40 banks while at the same time hijacking numerous shipments of illegal whiskey being smuggled into the state from the Bahamas. Indeed, Ashley's gang was so effective that rum-running on the Florida coast virtually ceased while the gang was active. His two-man raid on the West End in the Bahamas in 1924 marked the first time in over a century that American pirates had attacked a British Crown colony.
Among poor Florida "crackers", he was considered a folk hero who represented a symbol of resistance to bankers, lawmen and wealthy landowners. Ashley's activities also hindered Prohibition bootleggers in major cities, whose importation of foreign liquor undermined local moonshiners. Even the newspapers of the era frequently compared him to Jesse James. Almost every major crime in Florida was blamed on Ashley and his gang and one Florida official called him the greatest threat to the state since the Seminole Wars. His near 13-year feud with Palm Beach County Sheriff George B. Baker ended in the death of Ashley and his three lieutenants in 1924.
Biography Early life and Desoto Tiger murder John Ashley was born and raised in the backwoods country along the Caloosahatchee River in the community of Buckingham, Florida, near Fort Myers, Florida. He was one of nine children born to Joe Ashley, a poor Florida woodsman, who made his living by fishing, hunting, and trapping otters. The Ashley family moved from Fort Myers to Pompano in the 1890s, where Joe Ashley and his older sons worked on the new railroad being built by industrialist Henry Flagler.Burnett, Gene M. Florida's Past: People and Events That Shaped the State. Vol. 3. Sarasota: Pineapple Press Inc, 1996. (pg. 85-89) In 1911, Joe moved his family to West Palm Beach and briefly served as county sheriff. John Ashley spent much of his youth in the Florida Everglades and, like his father, became a skilled trapper and alligator hunter.Moran, Mark, Charlie Carlson and Mark Sceurman. Weird Florida: Your Travel Guide to Florida's Local Legends and Best Kept Secrets. New York: Sterling Publishing Company, 2009. (pg. 101-104)
On December 29, 1911, a dredging crew working near Lake Okeechobee discovered the body of Seminole trapper Desoto Tiger. An investigation was held and John Ashley soon came under suspicion. According to fellow Seminole Jimmy Gopher, Ashley had been last seen with Tiger traveling in a canoe together with a boatload of otter hides to sell at a local market. Authorities were later told by fur traders in Miami, the Girtman Brothers, that John Ashley had sold them the hides for $1,200; the previous day he had also been arrested in West Palm Beach on a charge of "recklessly displaying firearms". Two deputies, S.A. Barfield and Bob Hannon, found Ashley camping in a palmetto thicket near Hobe Sound and attempted to take him into custody. However, they were surprised by his brother Bob Ashley and were disarmed at gunpoint. John Ashley then sent the officers back with a message for Sheriff George B. Baker "not to send anymore chicken-hearted men with rifles or they are apt to get hurt".Reilly, Benjamin. Tropical Surge: A History of Ambition and Disaster on the Florida Shore. Sarasota: Pineapple Press Inc, 2005. (pg. 186-192) McGoun, William E. Southeast Florida Pioneers: The Palm and Treasure Coasts. Sarasota: Pineapple Press Inc, 1998. (pg. 136-140)
In his trial for the murder of Tiger in 1910, despite overwhelming evidence, Ashley was not convicted. In a second trial in 1915, he was sentenced to hang for Tiger's murder, but that conviction was overturned by the Florida Supreme Court. Ashley repeatedly escaped from various local jails and eluded law enforcement until he was gunned down at the St. Sebastian River bridge in Roseland.Kleinberg, Eliot. Palm Beach Past: The Best of "Post Time". Charleston, South Carolina: The History Press, 2006. (pg. 72) Although he was incarcerated for other crimes, Ashley never served any time for the murder of Desoto Tiger.
Formation of the Ashley Gang When the Seminole Nation raised protest over the murder, the US federal government threatened to intervene. John Ashley fled to New Orleans for a year or two before returning to Florida around 1914. He may have worked as a logger in Seattle, and later claimed to have robbed a bank in Canada. Upon his return, he surrendered himself to authorities in West Palm Beach where he was imprisoned until his trial. Ashley may have hoped that a hometown jury might sympathize with him, however the local prosecutor petitioned the judge for a change of venue to Miami. Hearing of the prosecutor's plans, he decided to escape. According to contemporary accounts, Ashley was being escorted to his cell by Sheriff Baker's son, Robert C. Baker, when he suddenly broke away, ran out an unlocked door and climbed a 10-foot fence to freedom.
He and his brothers then became outlaws and, with other occasional partners, formed a criminal gang. In 1915, he and Bob Ashley robbed an FEC passenger train with Chicago mobster Kid Lowe. Their first attempt was less than successful as they failed to agree on who would collect valuables from the passengers and who would rob the mail car. That same year, they stole $45,000 in silver and cash in a daring daylight bank robbery in Stuart, Florida. During their getaway however, Lowe accidentally shot John Ashley in the jaw, costing him the sight in one of his eyes.Ling, Sally J. Run the Rum In: South Florida During Prohibition. Charleston, South Carolina: The History Press, 2007. (pg. 87, 89, 91) When Ashley attempted to get medical attention for his eye, he was captured and held in the Dade County jailhouse to await trial. He was taken to Miami to stand trial for the murder of Tiger, however, the state's attorney believed that that had a better chance of prosecuting Ashley for the Stuart robberies in West Palm Beach.
On June 2, 1915, Bob Ashley attempted to break his brother John out of jail. Entering the jailer's house, Bob Ashley shot Deputy Sheriff Wilber W. Hendrickson at point-blank range and left with his jail keys. He then ran from the house to the garage where gang members had left him a getaway car. When he found he was unable to drive the particular car left for him, he attempted to force several men at gunpoint to drive the car for him. Each of the men claimed to not know how to drive the car either so Bob Ashley jumped on the running board of a passing truck and forced the driver, T.H. Duckett, to take him out of town. A deputy, officer J.R. Riblet, spotted Ashley and gave chase. When the truck suddenly stalled in the middle of the street, a shootout occurred resulting in the deaths of both Bob Ashley and Riblet. Angered by Bob's killing spree, several thousand Miami residents threatened the jailhouse and talked of lynching John Ashley in his cell. It was only after police paraded the body of Bob Ashley through the streets that the mob dispersed.
Kid Lowe, possibly out of guilt for shooting John Ashley, sent a note to Dade County sheriff Dan Hardie demanding the release of Ashley:
However, no attack from the Ashley Gang came and the town proceeded with the prosecution. On November 23, 1916, John Ashley pleaded guilty to robbery and was sentenced to 17 years in the state penitentiary at Raiford.
Ashley and the Queen of the Everglades Prior to his arrest, Ashley began a relationship with Laura Upthegrove. Upthegrove acted primarily as the gang's lookout. Whenever she heard authorities were nearing one of Ashley's hideouts, she would drive her car through secret backwoods trails, often without headlights if at night, to warn fellow gang members. Laura also cased banks and served as a getaway driver. While they were together, she became known as the "Queen of the Everglades", and took a central role in the gang while Ashley was incarcerated.
Escape and foray into piracy
Ashley behaved as a model prisoner for two years until escaping from a road camp, with the assistance of fellow bank robber Tom Maddox, on March 31, 1918. With the start of Prohibition, he began moonshining with his gang before his eventual recapture in June 1921. The Ashley gang continued moonshining in his absence, maintaining their many stills in the woods of central Florida, and began hijacking rum runners as well under Clarence Middleton or Roy Matthews. Joe Ashley had several stills in Palm Beach County while John's brothers Ed and Frank Ashley ran liquor from the Bahamas to Jupiter Inlet and Stuart. While John Ashley was still in jail, his brothers disappeared while on a return voyage from Bimini in October 1921.
The circumstances surrounding Ashley's third and final escape remain a mystery, only that he "vanished from his cell", and returned to bank robbery with his gang. In one of their more memorable robberies, the gang managed to rob the Stuart bank a second time in September 1923 after Ashley's teenage nephew Hanford Mobley sneaked into the building disguised as a woman and escaped with several thousand dollars. Shortly after the robbery, Mobley and Middleton were caught in Plant City and Matthews in Georgia, however all escaped and were back together in the woods near Gomez by the end of the year.
In November 1923, the gang robbed $23,000 in cash and securities from a bank in Pompano. Like many of their heists, this was followed by reckless celebrating in the streets. After wrapping the loot in a bedsheet, they slowly drove through the middle of the town in a stolen taxi. They waved a bottle of whiskey to onlookers and shouted "We got it all!". Leaving the town, they crossed a canal and disappeared into the swamp near Clewiston. Ashley supposedly left a bullet with one of the victims to give to Sheriff Baker if he "ever got out to the 'Glades".
The gang leader also tried his hand at piracy, intercepting many rum-runners along the coast of southern Florida. Many chose to pay the Ashleys protection money. In 1924, he and his nephew Hanford Mobley stole a sea skiff and led a raid against rum-runners in the Bahamas' West End leaving with $8,000 from four wholesale liquor warehouses. Hours before the raid, however, an express boat carrying a quarter-million dollars had left for Nassau.
Within a few years of Prohibition, the Ashley Gang was so feared by Florida bootleggers that many began deserting the area looking for safer routes far out of reach of the gang. As a result, the Ashleys' opportunities for liquor piracy dwindled and they eventually returned to bank robbery as their primary activity.
Feud with Sheriff Baker By this time, Ashley and Sheriff Baker were engaging in a personal feud. The sheriff had received a tip from a local car salesman and had set a trap on the eve of the Bahamas raid. Suspecting that the law might be on to his plans, Ashley changed his route at the last minute and sailed through St. Lucie Inlet, narrowly avoiding capture.
Baker spent months searching the Everglades and came up empty-handed. This was in part the result of help from fellow Florida "crackers" and a "grapevine telegraph of the 'glades". Per historian Steve Carr, Baker was a corrupt sheriff who wasn't above shaking down poor people trying to live off the land. Since he also had ties to the Ku Klux Klan, the local Black community helped the Ashley gang.