Bootlegging and Rum-Running in Jacksonville

October 13, 2011 20 comments Open printer friendly version of this article Print Article

Advocates for prohibition thought that once liquor licenses were revoked, reform organizations and churches could persuade the American public not to drink, smugglers would not oppose the new law, and saloons would disappear. However, the opposite effect would happen.

The Ashley Gang

The Ashley Gang was said to be a notorious group of desperados that terrorized Florida's southeast coast for more than 15 years, with ties to Jacksonville.  Although their specialty was running liquor between the Bahamas and South Florida, their crimes also included murder, bank robberies, hijackings, bootlegging and moonshining.  

Spearheaded by John Ashley, the Ashley Gang's connections to Jacksonville included John Ashley using the city as a hideout (his sister Daisy lived in Jacksonville) and his associate, Clarence Middleton, being from Jacksonville.

More than eight decades after he and his crime partners died in 1929, John Ashley continues to be one of the most intriguing figures in Florida history.

Many a relative of an Ashley Gang member has written to defend, or at least try to explain, the long-dead gangster.

Clyde Middleton wrote in January to tell us of his uncle, Clarence Middleton. “He was the second oldest son of Steven and Margeret Middleton, my grandparents. He had four brothers and three sisters living in Jacksonville; all are deceased now.

“His oldest brother, Jack, owned the Embassy Club and the Peacock Club in Jacksonville.

“Cecil, Clyde and Bruce all served honorably in World War II and became successful businessmen in Jacksonville after the war.

“Clarence probably got involved in rum running in the early ’20s and met up with some of the Ashley Gang in prison then fell in with them.

“He was one of the four men murdered on the San Sebastian bridge in 1924. He is buried beside his father in Jacksonville.”  Clyde refers, of course, to the evening of Nov. 1, 1924.

Deputies stopped Ashley and Middleton, along with Hanford Mobley and Ray “Shorty” Lynn, on a wooden bridge over the St. Sebastian River in what was then St. Lucie County.

They later said the men were shot trying to escape. But many believed they were assassinated by lawmen tired of being humiliated from Stuart to Miami by robberies, moonshining and murder.

In 1997, Ada Coats Williams, a retired teacher of creative writing at Fort Pierce’s Indian River State College, completed Florida’s Ashley Gang, the first book on the Ashleys since 1928.

A retired deputy who’d been on the bridge that night had confirmed to her in the 1950s that the men were shot while handcuffed, after John made a sudden move.

He had told her on the condition that she keep the secret until after all those involved had died.

The Jacksonville Pea Farm Cabbage Riot

In 1927, John Ashley's sweetheart Laura Upthegrove sparked the famous pea farm cabbage riot in a Jacksonville jail after being sentenced 30 days for being drunk and uppity.  Five days into her sentence, she started the riot over too much cabbage being on the menu.  To diffuse the situation, prison officials tear-gassed the women, threw her into solitary and served more cabbage.

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