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. 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. 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; 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. 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. When Ashley attempted to get medical attention for his eye, he was captured and held in the
Dade County jailhouse to await trial. 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. the local Black community helped the Ashley gang. In early 1924, Baker finally got a lead on Ashley's location. Through his informants, Baker learned that Ashley was staying with family members in a moonshiner's cabin hidden in a swamp about south of the Ashley family home. The short bushes and palmetto scrub made it very difficult, if not impossible, to approach the cabin, making it an ideal hideout. Baker was determined to capture Ashley and, with weapons from the
Florida National Guard and deputized civilians, made plans to surround the cabin and starve him out. On January 10, 1924, he sent eight of his deputies to the house early in the morning; they were in position by dawn. Just as the deputies were about to make their move, Ashley's dog began barking at the lawmen. The deputies fired at the dog, causing Ashley to return fire; he killed one of the deputies, the sheriff's cousin Fred Baker, in the resulting gunfight. His father, Joe Ashley, was killed in his bunk while his partner, Albert Miller, and Laura were seriously wounded by buckshot from a deputy's shotgun. Forced to leave his wife behind, Ashley escaped through a secret entrance; his wife's screaming caused the deputies to hold their fire, which helped enable the escape. Despite a manhunt involving 200 men, during which the homes of both Joe Ashley and Hanford Mobley were burned (as well as a small grocery owned by Miller), Ashley remained in the area where Laura was being held by police. He hoped to plan a jail break for her, as well as avenge the death of his father, but as more time passed he left for
California to lie low.
Death Ashley returned to Florida and spent several months with his gang planning their revenge. He apparently developed a plot to kill Sheriff Baker at the Jacksonville courthouse following his election in November. On November 1, 1924, Baker received a tip from an anonymous source, believed to be a gang member's girlfriend (or a disgruntled brother-in-law), that Ashley would be travelling up the coast on the
Dixie Highway to rob a bank in
Jacksonville. That same day, Baker arranged an ambush at the bridge over the St. Sebastian River in Roseland, blocking the road with a chain with a red lantern across the bridge. As the bridge was out of his jurisdiction, the actual operation was overseen by the sheriff of
St. Lucie County, J.R. Merritt, along with three of Baker's deputies. An hour after the ambush was laid, Ashley's black touring car was spotted. Once it stopped at the bridge, the deputies approached the car from behind and ordered the gang out of the vehicle. According to the official story, the deputies searched the car and found several guns while Ashley, Ray Lynn, Hanford Mobley, and Clarence Middleton were lined up outside the car. John Ashley then pulled out a concealed weapon, causing the deputies to open fire. Ashley and his three partners were killed in the shootout. There are two alternate versions, however. The first, according to two men who witnessed their arrest, claim they had also been stopped on the bridge and saw the officers approach Ashley's car behind them. When police directed them to leave the scene, both men insisted that Ashley and the others were handcuffed. There were marks that could have been made by handcuffs, however police claimed the marks were the result of the coroner examining the bodies. This explanation was accepted by a
coroner's jury. A third theory, one thought to be closer to the truth, was offered in the 1996 book ''Florida's Ashley Gang'' by historian Ada Coats Williams: an unidentified deputy claimed that, while in handcuffs, Ashley made a sudden move forward and dropped his hands, causing officers to fire. He had told Williams this during the 1950s on the promise that she not reveal this information until all the deputies had died. At the time of Ashley's death, however, it was widely believed among poor "crackers" that he had been executed by the police as a form of
frontier justice.
Aftermath After her husband's death, Laura Upthegrove lived under an assumed name in western Florida for a time. In the next two years, she was arrested on several occasions before eventually opening a gas station at
Canal Point on Lake Okeechobee. She later moved in with her mother in
Upthegrove Beach. On August 6, 1927, she died during an argument with a man trying to buy moonshine from her. In the heat of the moment, she swallowed a bottle of disinfectant and died within minutes. It is unclear whether it was an accident, as some claim she mistook it for a bottle of gin, but it was widely reported that she had committed suicide. She was 30 years old. A few members of the Ashley gang still remained, although they were eventually killed, captured, or fled the state within a few years. Only $32,000 of the gang's fortune was ever recovered; it was found only with the help of ex-gang member Joe Tracy. A reported $110,000 and other Everglades stashes have never been reported as found. Ashley, Mobley, and Lynn (Middleton was buried in Jacksonville) were buried in a
family cemetery, the Little Ashley Cemetery, outside Gomez, where the Ashley family home once stood. Six members of the Ashley clan were buried there, all having died a violent death with the exception of an infant grandchild. The cemetery eventually became part of an
exclusive residential neighborhood, Mariner Sands, and it is rumored that some unrecovered loot is buried somewhere on this property. A state
historical marker was placed at Sebastian Inlet but disappeared when a new bridge was built over the river. ==In popular culture==