The Ashley Gang’s Reign of Rebellion

In the shadows of 20th-century Florida, where cypress knees rose like sentinels and sawgrass stretched for miles, a legend took root, one that still echoes through the Glades today. The Ashley Gang, led by the enigmatic John Ashley and his partner-in-crime Laura Upthegrove, carved a path of rebellion, romance, and lawlessness that some say rivaled the Seminole Wars in its defiance of state control. 

"To understand the Ashley Gang, you have to understand the Everglades - not just as a place, but as a force of nature," says Aubrey Brown, creator of Florida.Folk.History on Instagram. “John Ashley grew up on the edge of the St. Lucie River, the son of a trapper and trader. He wasn’t just some petty outlaw out for fast money. He was shaped by the frontier, by poverty, and by a deep-rooted distrust of authority.” 

Ashley’s descent into notoriety began in 1911 with the alleged murder of Desoto Tiger, a Seminole man. Though arrested, Ashley never stood trial. Instead, he vanished into the wilderness, setting off what would become a decade-long saga of jailbreaks, bank heists, and Prohibition-era bootlegging. “Some say he did it. Others believe he was framed,” Brown notes. “Either way, it lit the fuse.” 

The Ashley Gang struck banks from Stuart to Miami and hijacked rum shipments bound for the East Coast during Prohibition, amassing an estimated $1 million - an astronomical sum for the time. “In comparison, Bonnie and Clyde robbed only robbed in the thousands,” said Brown.  

Ashley's deep knowledge of the Everglades allowed him to disappear without a trace, moving at night along old Seminole trails. “Lawmen would chase them in and get turned around, lost in the maze,” Brown says. “They disappeared like smoke.” 

But the legend of the Ashley Gang is inseparable from the woman by John’s side - Laura Upthegrove, often referred to as the “Queen of the Everglades.” “And she earned that title,” said Brown. Far from a mere romantic figure, Laura was a force in her own right. She drove getaway cars, smuggled liquor, and was known to carry a pistol on her hip. “Her life before Ashley was hard - early marriage, poverty, a sense of being caged in,” says Brown. “With him, she found freedom and power. Some even say she was the true brains of the operation.” 

Their defiance struck a chord with working-class Floridians. At a time when banks were foreclosing on farms, politicians were entangled with big business, and the state was selling off land to railroads, the Ashley Gang became folk heroes to many. “[They] looked more like rebels than criminals,” Brown explains. “They robbed the rich, outran corrupt sheriffs, and made fools of the system.” 

The gang’s reign ended in 1924 on the Sebastian River Bridge. According to official reports, Ashley and several members were killed in a shootout. But suspicion lingers. “Many believe it was an execution,” Brown says. “Their guns were still in their holsters.” 

Laura Upthegrove didn’t live long after Ashley’s death. She died in 1927 under mysterious circumstances - Lysol poisoning, possibly suicide or accident. “Some say she died from heartbreak and addiction,” Brown added. She was just 30 years old. 

Their story has been dramatized, most notably in the 1973 film Little Laura and Big John, but Brown cautions against taking such portrayals at face value. “It turns Laura into a lovesick girl and John into a tragic antihero, which misses the truth. They were two broken, brilliant, dangerous people who challenged the system in one of the wildest corners of America.” 

Today, the Ashley Gang’s story lives on not in statues or museums, but in whispers carried by the Everglades breeze. “You won’t find many markers with their names,” Brown said. “But their story rides through the cane fields and across the water. It’s the story of a Florida that once was - untamed, defiant, and free.” 

You can find thrilling stories like the Ashley Gang and more on Aubrey Brown’s Instagram account, @Florida.Folk.History, where she brings the Sunshine State’s hidden past to life through bite-sized storytelling, archival photos, and field research. Brown studied art and marketing but always felt drawn to history. What began as a personal search to reconnect with her Florida roots has grown into a widely followed platform celebrating overlooked legends, unsung heroes, and the folklore that textbooks leave behind. “Florida history isn’t just what you find in a museum,” she says. “It’s what’s whispered in barrooms, passed down in kitchens, and hidden in the sawgrass.”