In Prohibition-era Florida and before, you didn’t want to get on the wrong side of John Ashley and Laura Upthegrove.

Move over Bonnie and Clyde. Two decades before your crime spree, South Florida had its own outlaw couple. Meet John Ashley, “King of the Everglades,” and Laura Upthegrove, “Queen of the Everglades.”

While the Ashley Gang operated up and down the Florida coast, John Ashley’s first notorious act came within Broward’s borders in 1911. It was then that the son of Tommy Tiger, chieftain of the Cow Creek Seminoles, was found dead in a canal. Many crimes later, including murder, bank robbery and the hijacking of rumrunners, came the looting of a Pompano bank in 1923.

Pompano figures prominently in the story since Joe Ashley, John’s father, brought his wife and five sons from the Gulf Coast to Pompano Beach in 1904. They moved to West Palm Beach in 1911. Joe chopped wood for the railroad, but the family of farmers also hunted alligators and otters.

According to an account in The Palm Beach Post, “Young John was an expert trapper in the then-expansive Everglades – and a crack shot.” A relative said, “I never saw a more mannerly or nicer boy in my life… He always came in with a smile and a pleasant word for all.”

According to this account, John Ashley would leave food for needy people. He ditched one bank robbery after learning the bank president was a childhood playmate.

Of course, Tommy Tiger was not as appreciative, nor were sheriff deputies investigating the murder of his son, Desoto Tiger. It all pointed to Ashley, who killed the Seminole after robbing him of furs meant for trade.

Palm Beach County Sheriff George Baker sent two deputies to Ashley’s home. But brother Bob – one of three brothers pulled into the gang’s enterprises – surprised the two deputies with a gun and disarmed them. John appeared and sent the pair off, telling them: “Tell Baker not to send any more chicken-hearted men with rifles or they are apt to get hurt.”

Ashley was given a third name, “Swamp Bandit,” as he adopted hideouts in the Everglades during the crime spree that came after the Seminole killing. His gang hit at least 40 banks and netted nearly $1 million – equivalent to more than $12 million today.

The Ashley Gang added to the bank hauls by hijacking shipments of illegal whiskey being smuggled in from the Bahamas. According to one account, Ashley’s gang was so pervasive that rumrunning in South Florida almost ceased while the group was active. But the rumrunning/hijacking had a cost. Two of the Ashley brothers, Ed and Frank, lost their lives on one of these escapades near Bimini.

Meanwhile, the cops-and-robbers chase went on from Palm Beach to Dade, with all kinds of encounters. In one, John Ashley lost an eye. He and brother Bob, along with a tough named Kid Lowe, were attempting to rob a Stuart bank when cops appeared and a shootout began. A shot fired by Lowe accidently blew out John’s jaw and injured his left eye.

John was captured and later fitted with a glass eye. Not long after, he escaped jail.

Laura was said to be a large woman with dark hair, a gal who wore a .38-caliber revolver strapped to her waist. She not only cased banks to be robbed; she also masterminded some of the gang’s schemes. She was the lookout on secret Everglade trails that led to hideouts and moonshine stills.

In 1924 came a year of reckoning for the family. Ashley’s father Joe, who was also drawn into the gang’s plunder, was killed in a raid on one of the stills.

Later that year, John and three others were surprised by authorities who had been tipped off about the gang’s plan to rob a Jacksonville bank. The four were shot and killed on a bridge over the St. Sebastian River. But they died under suspicious circumstances: Were they in handcuffs when shot? John was 36.

If all this sounds like a movie, it already is. The low-budget film “Little Laura and Big John” is one very few have ever seen, possibly because Fabian (more known for crooning than acting) played John Ashley. The movie was partially based on a 1928 book, The Notorious Ashley Gang.

In the end Ashley became a hero to some so-called “Florida crackers” who were resentful of big banks and intrusive lawmen.

What of the other brother, Bill Ashley? He must have kept his head down, or had a different frame of mind. He settled in Pompano Beach and died in 1940. His mother, who had seen a husband and four sons perish in infamy, survived all of them, passing on in 1946.

To read the second part of this story, click here.


Leave a Reply

Your email address will not be published. Required fields are marked *