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 Liquor Czar: The Whiskey King of Duval County

John Hysler, known as the Whiskey King of Duval County, was gunned down on the Acosta Bridge by Hope King, a prohibition agent, in 1928. Hysler was quoted as saying "My God, he hit me all over, I'm full of lead." Alleged to be connected to Al Capone, Hysler was on his way back to Jacksonville on a bootleg-whiskey run to Mineral City (present day Ponte Vedra Beach).  Hooch was known to come ashore in Mineral City from Rum Row.

John Hysler was gunned down during a moonshine run on the Acosta Bridge in 1928.

"You mean you really have not heard about what happened to John Hysler today?"
The owner shook his head, put the $5.00 in his pocket and leaned in a little closer to the reporter who told him,"He's dead".

The owner turned and yelled to his short order cook,"Oh my God. Hey Mert,come out heya.Johnny's dead!"
A sweat covered fellow popped his head around the door way and said,"ya kiddin'? Dead?
How? He was here this mornin' for some scrambled eggs and calves brains..."

The thought of that delightful breakfast dish made the meatloaf he half scarfed down not so bad after all to the newsman.

"Two Probbies got him..the prohibition agents...from Jacksonville.They got word he was to be running red whiskey up to Jacksonville.
They shot him on the St Johns River Bridge.Seems they don't know who shot first. Agent King or Hysler. They both empted their guns.The agent was hit in the chest and ankle but kept firing his 45 automatic. Hysler was hit in the shoulder, twice in the neck and twice in the chest.He was alive when Agent Eaton got him to St. Vincents hospital but he died about 7 tonight."

The reporter looked over at the cook,who still stood by the door. He was wiping away what seemed to be tears.
'He was a good joe,ya know? So he ran some shiner around these parts.Folks gotta survive. Them yankees pay real good money for that Cuban rum I hear. Shoot, he even was bringin' in some real classy folks- some of them Italians from Chicago. 'Member that boss? That flashy guy named Al?"

The reporter perked up,"I heard the Hysler boys were in business dealings with Al Capone".

Mert just shook his head and backed into the kitchen,"he was just a real good joe".
Days later, the funeral for John Hysler was the most anticipated quasi-social event of the decade.
Almost 1,500 upstanding 'law abiding' citizens packed the funeral.
Flower arrangements from some of the nations wealthiest flowed from the building into the street.
Cops,lawyers,politicians were all pallbearers.

Image courtesy of wikipedia.

The Hsyler family was said to have connections with Chicago mobster Al Capone (image courtesy of wikipedia), who was known to frequent Jacksonville at times.

Image courtesy of

When the entire United States went dry, Demon Rum became illegal everywhere in the country… but Cuba, Puerto Rico and the Bahamas lay with in the range of bootlegger speedboats which operated out of Jacksonville.

In 1928, notorious underworld figure Al Capone bought a 32 foot powerboat, Flying Cloud, in Jacksonville. He used it for parties and to travel between Jacksonville and a home in Miami — and possibly for rum running. In 1933 Capone was put in prison for tax evasion and later his boat was put up for sale to satisfy his debts.

Local and federal revenue agents fought the illegal importation of liquor.

When smugglers saw revenue cutters approaching, they dashed for shallow water and threw cases of whiskey overboard attached to marker buoys. But if the revenuers saw the buoys, they’d confiscate the liquor. So, when they threw the liquor overboard, the bootleggers anchored their buoys underwater with heavy bags of salt.

In a few hours, after the revenuers left, water dissolved the salt, the buoy floated to the surface, and the smugglers would retrieve their cargo…

Until the sheriff learned that slick trick.

In spite of the Law’s best efforts Jacksonville remained soaking wet while legally dry.

The Ashley Gang on next page.

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