Sunday Favorites: Outlaws of the Everglades

One of my all-time favorite historical fiction novels is Red Grass River by James Carlos Blake. It's a riveting tale of moonshine, vengeance, and outlaws set in the blood-soaked sawgrass of Florida's backcountry. It's gritty, lyrical, and just barely exaggerated. because the truth behind the novel, the story of the Ashley Gang, is even wilder.

According to The Ashley Gang – West Palm Beach History, the story, much like the book, begins with a murder that shocked early South Florida: the killing of Seminole trapper Desoto Tiger in late 1911. Desoto, son of Cow Creek Seminole leader Tommy Tiger and a veteran of the Third Seminole War, was last seen paddling a canoe full of otter pelts with a young man named John Ashley. Days later, Desoto’s body was found floating in the New River Canal, shot in the back. A signed receipt for 84 pelts worth $1,200 at a Miami trading post sealed the case: J. Ashley.

Sheriff George B. Baker sent deputies to arrest John at his family’s swamp hideout in Gomez, just north of Hobe Sound. But John and his brother Bob were ready. Hidden in the palmettos, John warned the deputies off with a calm menace and let them go—on the condition they deliver a message: don’t send any more “chicken-hearted men.” It was the birth of an outlaw legend.

The Ashley family had arrived in West Palm Beach in 1911, part of the great migration of white settlers chasing work and opportunity in the newly developing tropics. Patriarch Joe Ashley worked briefly as a lawman, helped build Henry Flagler’s railroad, and distilled some of the best moonshine south of the Georgia line. A former backwoodsman with nine kids, Joe raised his five sons, John, Bob, Ed, Frank, and Bill, to survive in the unforgiving Everglades. They trapped otters, hunted gators, and knew the swamp like Seminoles.

John Ashley fled the murder charges to New Orleans but returned two years later, homesick. He turned himself in, only to escape jail in dramatic fashion—leaping a ten-foot fence while holding a plate of home-cooked food. The Ashley Gang was born.

By 1915, they had robbed the Bank of Stuart and tried to hit a train near town. During the heist, a bullet shattered John’s jaw and blinded him in one eye. Captured and tried for the Tiger murder, he beat the rap by pleading guilty to bank robbery instead.

Prison was temporary. John escaped in 1918 and returned to crime, just in time for Prohibition. The gang shifted from banks to booze, running rum from the Bahamas to Florida’s mangrove-choked coastline. They had speedboats, moonshine stills, and hideouts deep in the 'Glades. With his brothers, John built an empire on liquor and lead.

But 1920 brought two great changes. Sheriff George Baker died and was replaced by his son Robert C. Baker who made it a personal mission to destroy the Ashleys. And John met the love of his life: Laura Beatrice Upthegrove.

Laura, the so-called Queen of the Everglades, was unlike any outlaw moll you've ever read about. Packing a revolver and a don’t-cross-me attitude, she cased banks, warned the gang of police raids, and earned their respect. She also gave John something to lose.

Then came the nightmare. While John was back in prison, he dreamed his brothers Ed and Frank were ambushed and killed. Not long after, they vanished on a rum run to Bimini. Three rival bootleggers, Davis, Stokes, and White, were later found dead. John may have been behind bars, but his reach extended far.

When he escaped again in 1923, the Ashley Gang launched a final spree of robberies. But the townsfolk had had enough. After a firefight left Joe Ashley and Deputy Fred Baker dead, the public turned on them. Their hideouts were torched. Allies disappeared.

On November 1, 1924, they were betrayed by John’s own brother-in-law, who tipped off the police. A trap was set at the Sebastian River Bridge. The lawmen claimed the gang resisted arrest. In truth, according to a deputy who later confessed, they were executed on the spot.

John Ashley, Hanford Mobley, Clarence Middleton, and Ray “Shorty” Lynn were gunned down. John’s glass eye—a macabre trademark—was sent to Sheriff Baker. Laura, devastated, sent a promise: “If you don’t put back that eye, I’ll crawl through Hell on my hands and knees to kill you.” The eye was returned, and John was buried in Gomez.

Laura Upthegrove didn’t last much longer. In 1927, after an argument at her gas station in Canal Point, she accidentally drank Lysol thinking it was gin. She died writhing on the floor while her mother looked on, unmoved. She was only thirty.

The Ashley Gang’s reign lasted less than a decade, but their legend has never died. They were outlaws and murderers, yes—but also folk heroes to some, symbols of rebellion in a rapidly changing Florida.

Their tale is one of myth, moss, and mayhem. And like any good Southern gothic—especially one penned by James Carlos Blake—it blurs the line between truth and tall tale.

But make no mistake: the Ashley Gang was real. And for a time, they ruled the swamps.