The King and Queen of the Everglades

Florida gangster

John Ashley was a notorious Florida gangster.

The Florida Everglades remained unexplored for quite some time, and was even considered impenetrable by some of the original natives to the surrounding land. Because of the elusive and hidden nature of the Everglades, it should come as no surprise then that it provided sanctuary to some of America’s most notorious criminals during the early 1900’s. One such bandit, John Ashley, along with his girlfriend, Laura Upthegrove, were so active in southern Florida between 1915 and 1924 that collectively they became known as the “King and Queen of the Everglades.”

John Ashley, who also occasionally went by the nickname of “Swamp Bandit,” was a bank robber, bootlegger, occasional pirate, and overall American outlaw, who was raised in the backwoods of the Caloosahatchee River near what is today considered Fort Myers. His father was a railroad worker and otter trapper who made a living out of fishing and hunting, and John followed in his footsteps, becoming a skilled trapper and alligator hunter by a very young age.

John Ashley’s first reported crime was the suspected murder of fellow otter trapper Desoto Tiger in 1911, though due to the intervention of one of his brothers, authorities were unable to arrest him for the crime. Afterwards, John spent a few years on the run in nearby states with his brothers, eventually forming a gang with his brothers and other outlaws they had met in their travels. This gang of robbers and murderers were estimated to have collected more than $1 million from over forty banks in the southern United States during the time that they were active, and became known simply as the Ashley Gang.

Prior to an arrest in 1915 during an attempted break-out for one of his jailed brothers, John began a relationship with Laura Upthegrove. Laura immediately took an active role in the gang, marrying John and acting as both a look-out and getaway driver during robberies, and earning herself the nickname of “Queen of the Everglades.” During John’s incarceration, the Ashley Gang remained active in South Florida, even adding moonshining and rum running to their repertoire, and Laura took on a central role in the business during John’s absence, keeping her role even after his death.

Though a skilled criminal, eventually able to escape from prison after only a few short years, John’s thirst for revenge turned out to be his downfall. Through the course of his legal troubles, John developed a feud with a local authority, Sheriff Baker, a feud which lasted for thirteen years. After remaining safe in California for a couple of years, John returned to Florida in 1924 to make an attempt on the Sheriff’s life. Things took a turn for the worse when the Sheriff received an anonymous tip on John’s location, and an intense police shoot-out ensued. John and three of his gang partners were killed in the event.

During his time as an outlaw, John Ashley became somewhat of a hero among the poor Florida “crackers” in the area. While his name might not be as well known as other gangsters from his era, at one point in time he and his gang were believed to be responsible for every major crime that happened in the state of Florida, and one state official even referred to John and his gang as the greatest threat to Florida “since the Seminole wars.” One thing is for sure, the so-called “King of the Everglades” certainly made his mark on South Florida’s history, and will never be forgotten.

To see some of the Everglades mangrove forests once utilized by John and his gang for hiding, take the family on an Everglades swamp tour. Many of these areas can only be accessed and experienced by boat, and an airboat ride is the perfect way to get up close and personal while safely enjoying some of Florida’s history.