The Ashley Gang rides again 

Visitors check out the Ashley Gang
Visitors check out the Ashley Gang permanent exhibit at the Elliott Museum in Stuart. GREGORY ENNS

The shootout with lawmen at the Sebastian River Bridge that left John Ashley and three of his gang members dead happened exactly a century ago come Nov. 1. Yet the story continues to fascinate. You only have to see the throngs visiting the Elliott Museum in Stuart, which recently created a permanent Ashley Gang exhibit, to understand the public’s enduring interest. 


The saga of the Ashley Gang has multiple elements for becoming Florida’s crime story of the 20th century: a handsome leader whose romantic partner is also a criminal, multiple killings, bootlegging, a blood feud with lawmen, bank and train robberies and jail escapes. 

Until their ignominious end, John Ashley and his gang for a decade roamed South Florida, thumbing their nose at law enforcement and doing what they will. 

John Ashley’s known criminal activities began at the end of 1911, when he killed DeSoto Tiger, a Seminole Indian, and robbed him of 84 otter pelts. Given the gravity of the crime and his age at the time, 23, it is likely he had been walking on the wrong side of the law for years. 

The story of the Ashley Gang unfolded before the advent of television and even before radios came into popular use. It occurred when newspapers reigned supreme and were the only means of receiving news, except word of mouth. The story of the Ashley Gang, in perhaps a perverse way, was a form of entertainment in its day. 

Local newspapers delighted in reporting every available Ashley Gang detail. The news was received by readers with both familiarity and fear: familiarity because many people knew at least some members of the large Ashley family — John Ashley had eight siblings — and fear because while most of the gang’s shootouts occurred with lawmen there was always the chance that bystanders could be caught in the crossfire. 

Despite the fear, in an age of robber barons and a wider gap between the rich and poor Florida settlers, the gang enjoyed a surprising amount of public support. John Ashley represented the ultimate challenge to institutions of “the establishment’’ such as banks, railways and law enforcement. 

Another appeal of the Ashley story is the element of family loyalty, making it popular for the same reason The Godfather movie series remains perennially viewed. While there were certainly law-abiding Ashleys, John’s parents and at least three of his siblings stood by him, some of them joining in his criminal activities. 

Undoubtedly, there are more reasons for the appeal of the Ashley Gang story, and we hope to explore them as we bring you the three-part Ashley Gang series starting with this issue. 





Gregory Enns
Reach Gregory Enns or 772.940.9005.

See the original article in print publication

April 29, 2024


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