Bootlegging and Rum-Running in Jacksonville
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 innovation of Americans to get what they wanted was evident in the resourcefulness used to obtain alcohol during prohibition. This era saw the rise of the speakeasy, home distiller, bootlegger, rum-runner and many gangster myths associated with it. While city's like Chicago, Detroit and New York are typically associated with the era, Jacksonville was also at the forefront of illicit activity. During the late 1920s, many national magazines and the northern press labeled the "Gateway to Florida" as one of the most violent cities on the planet. While many events from this era have been forgotten, here are a few characters who left their mark on prohibition era Jacksonville.
The Real McCoy
The term "The Real McCoy" is said to originate from a prohibition-era Jacksonville boatyard owner and rum-runner named William Frederick McCoy. While popular crime figures like Al Capone and the Purple Gang were running Chicago and Detroit, McCoy was in control of Atlantic Ocean rum-running between the Bahamas and Canada. That's a pretty big accomplishment for a Jacksonville boatyard owner.
![](https://photos.metrojacksonville.com/photos/1519268472_BqB6NCf-M.jpg)
![](https://photos.metrojacksonville.com/photos/1519268490_bqbLCsn-M.jpg)
The Liquor Czar: The Whiskey King of Duval County on next page.
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.
![](https://photos.metrojacksonville.com/photos/1519291196_Jd2mHkw-M.jpg)
John Hysler was gunned down during a moonshine run on the Acosta Bridge in 1928.
![](https://photos.metrojacksonville.com/photos/1519323593_xMbjms6-M.jpg)
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.
![](https://photos.metrojacksonville.com/photos/1519389356_6r7NLQ9-M.jpg)
Image courtesy of https://www.cowart.info/blog/?m=200712&paged=2
The Ashley Gang on next page.
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.
![](https://photos.metrojacksonville.com/photos/1519268451_3cD58Pq-M.jpg)
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.
https://history.jupiter.fl.us/History/Ashley_Gang.cfm
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.
The Whisper Sisters on Next page
The Whisper Sisters
During Prohibition, Jacksonville was a major port of entry and manufacturing center for hooch. It was a very easy way to turn $200 into $2,000, according to one North Florida still operator. What is not known is that for every male in the business, there was an opportunistic female to meet his match. It can be argued that the Whisper Sisters were the best.
Lyndall McMurray
You can't have a story about Prohibition and not mention Springfield, one of Jacksonville's most colorful historic neighborhoods. In 1926, Mrs. Lyndall McMurray became a Prohibition-era celebrity among First Coast women. Mrs. McMurray was known to sell soda pop in front of a Main Street tent, and hooch out the back. It was said she shot her man to death on a Springfield street because he mistreated her after she stole ten cases of whiskey from him. She was found not guilty in front of a courtroom packed with women.
Sheriff W.H. "Ham" Dowling
Ham Dowling was a man who thought he was above the law. Dowling, a former SAL train conductor and son of a Baptist minister, was elected Duval County sheriff in 1912 on a strong law-and-order campaign against "a carnival of crime." In 1917, Governor Sidney Catts suspended him for lax enforcement of anti-liquor laws but he was reinstated a few months later. Five years later, he was suspended by Governor Cary Hardee on a conspiracy charge but was later reinstated. In 1928, W.B. Cahoon was elected over the long-time sheriff and commenced bare-knuckle law enforcement that Jacksonville had not seen during most of the Prohibition era under Dowling.
Not surprisingly, two years later Dowling was in the news again. This time for being busted for the ownership of two stills with 14,000 gallons of beer, 250 gallons of whiskey and 79 bottles of home brew. Dowling ended up being sentenced in 1931 to two years in a federal prison in Atlanta.
Source: https://jacksonville.com/tu-online/stories/062099/met_2b1Foley.html
![](https://photos.metrojacksonville.com/photos/1519268505_QkgDpq3-M.jpg)
A 1930s-era moonshine still busted by Sheriff W.B. Cahoon. Below, Sheriff W.B. Cahoon destroys a downtown still.
![](https://photos.metrojacksonville.com/photos/1519334014_xWmTr2N-M.jpg)
Sheriff W.B. Cahoon images courtesy of the State Archives of Florida.
Dowling wasn't the only public official busted during prohibition. Practically the entire South Jacksonville city administration, including the mayor, the chief of police, the president of the city council, the city commissioner, and the fire chief, were indicted by a federal grand jury as well.
Source: https://www2.potsdam.edu/hansondj/Controversies/1091124904_6.html
Henry "Skimp" Tillman
Skimp Tillman was one of the most notorious one-eyed barkeeps in Jacksonville during the 1930s. Tillman was known to use fists, guns and knives to settle disputes in downtown Jacksonville. Over a course of 20 years, he had been charged with assault to murder, to protect his well being six times, including shooting a customer to death in 1935. Skimp's luck of getting away with murder would end with the Court of Circuit Judge Bryan Simpson in 1948, after the shooting death of another customer.
![](https://photos.metrojacksonville.com/photos/1519291202_nCKRDBg-M.jpg)
Inside Jimmy Mains bar in 1933.
https://jacksonville.com/tu-online/stories/061000/nef_3257700.html
After being found guilty of first-degree murder, Skimp Tillman was electrocuted on June 5, 1949.
William Ostner: Father of the Six Pack
What would a Prohibition-era story be without mentioning the brewmaster who brought a full-scale brewery to town? Jax Beer was said to be the beer of the common man and the woman who smoked menthols, of the bon-vivant in a blue collar and the siren in Evening in Paris.
This brewery's start dates back to Moncrief Park, a full decade before Prohibition. In 1910, Moncrief Park's horse racing track drew spectators from all over the country. One of those spectators was William Ostner, a German-born brewmaster living in St. Louis.
![](https://photos.metrojacksonville.com/photos/1519350737_3rzSMK8-M.jpg)
The Jax Brewing Company facilities in 1959. Image courtesy of www.beercanhistory.com
Soon, Ostner would move to Jacksonville and set up the Jax Brewery Company on 16th Street, only to see the racetrack close and Prohibition enacted. During Prohibition, the company's name would change to Jax Cold Storage Company. In 1933, a week after the repeal of Prohibition, brews were rolling off the production line once again. After World War II, the Ostners bought 100,000 durable stacks from Towers Hardware, emblazoned Jax Beer on them, and sold beer six to a sack, and the concept of the six-pack is history. In 1957, the company was sold to Jax Brewing of New Orleans and the plant was converted into a major cold storage warehouse.
Article by Ennis Davis.
The Real McCoy
The term "The Real McCoy" is said to originate from a prohibition-era Jacksonville boatyard owner and rum-runner named William Frederick McCoy. While popular crime figures like Al Capone and the Purple Gang were running Chicago and Detroit, McCoy was in control of Atlantic Ocean rum-running between the Bahamas and Canada. That's a pretty big accomplishment for a Jacksonville boatyard owner.
![](https://photos.metrojacksonville.com/photos/1519268472_BqB6NCf-M.jpg)
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Rum-running also saw a revival as a trade in the United States. Liquor was smuggled in station wagons, trucks and boats from Mexico, Europe, Canada and the Caribbean. The term “The Real McCoy” came out of this era. It’s attributed to Captain William S. McCoy who facilitated most of the rum running via ships during prohibition and would never water down his imports, making his the “real” thing. McCoy, a non-drinker himself, began running rum from the Caribbean into Florida shortly after the beginning of prohibition. One encounter with the Coast Guard shortly thereafter stopped McCoy from completing runs on his own. The innovative McCoy set up a network of smaller ships that would meet his boat just outside U.S. waters and carry his supplies into the country.https://cocktails.about.com/od/history/a/prohibition_3.htm
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Also known as "Bill," McCoy was a sea captain and rum runner smuggler during the Prohibition in the United States. In pursuing the trade of smuggling alcohol from the Bahamas to the Eastern Seaboard, Capt. McCoy, a nondrinker who never touched liquor, found a role model in John Hancock of pre-revolutionary Boston and considered himself an "honest lawbreaker." McCoy took pride in the fact that he never paid a cent to organized crime, politicians, or law enforcement for protection. Unlike many operations that illegally produced and smuggled alcohol for consumption during Prohibition, McCoy sold his merchandise unadulterated, uncut and clean.https://en.wikipedia.org/wiki/William_McCoy_(bootlegger)
Around 1900, the McCoy family moved to a small Florida town named Holly Hill, just north of Daytona Beach. William and his brother Ben operated a motor boat service and a boat yard in Holly Hill and Jacksonville. By 1918, having constructed vessels for millionaire customers that included Andrew Carnegie and the Vanderbilts among others, McCoy earned a reputation for being a skilled yacht builder.
McCoy during Prohibition on next page.
McCoy during Prohibition
During Prohibition (1920–33), the McCoy brothers fell on hard times. Their excursion and freight business could not compete with the new highways and buses being built up and down the coast and across Florida. Needing money, the two brothers made a decision to go into rum-running. They sold the assets of their business, traveled to Gloucester, Massachusetts, and bought the schooner Henry L. Marshall.
McCoy then began to smuggle whisky into the U.S., traveling from Nassau and Bimini in the Bahamas to the east coast of the United States, spending most time dealing on "Rum row" off Long Island. After a few successful trips smuggling liquor off the coast of the United States, Bill McCoy had enough money to buy the schooner Arethusa. Placing the schooner under British registry in order to avoid being subjected to U.S. law, Bill renamed the vessel Tomoka (after the name of the River that runs through his hometown of Holly Hill).
McCoy made a number of successful trips aboard the Tomoka, and - along with the Henry L. Marshall and up to five other vessels - became a household name through his smuggling activities. Capt. McCoy mostly hauled Rye, Irish and Canadian whiskey as well as other fine liquors and wines. He is credited with inventing the "burlock" -- a package holding six bottles jacketed in straw, three on the bottom, then two, then one, the whole sewed tightly in burlap. It was economical of space and easy to handle and stow. These were generally known in the Coast Guard as "sacks." McCoy's legend grew as his quality liquor and fair-dealing perpetuated the phrase: "it's the real McCoy."
McCoy also became an enemy of the U.S. Government and organized crime. When the Coast Guard discovered McCoy, he established the system of anchoring large ships off the coast in international waters and selling liquor to smaller ships that transferred it to the shore. McCoy also smuggled liquor and spirits from the French islands of Saint-Pierre and Miquelon located south of Newfoundland.
Capture and arraignment
On November 23, 1923, the U.S. Coast Guard Cutter Seneca, had orders to capture Bill McCoy and the Tomoka, even if in international waters. A boarding party boarded the Tomoka, but McCoy refused to surrender. The Tomoka tried to flee, but the Seneca placed a shell just off the hull, and Bill McCoy's days as a rum-runner were over. The New York Times article that reported on the capture and arraignment of McCoy described the incident:
The report to Collector Elting showed that the Tomaka was first boarded by Lieut. Commander Perkins of the Coast Guard cutter Seneca, who ordered the crew keep silent. The bow of the schooner then was turned out to sea, and when the commander of the cutter observed the movement, he sent a shot across the bow of the Tomaka. She returned the fire with a machine gun set up on her forward deck. The machine gunners ran to cover when the shells of the Seneca began to fall so close to their mark that they kicked the spray over the Tomaka's deck.
McCoy described the chase that led to his capture:
When the Tomoka was boarded under cover of the Seneca's guns, I immediately set sail and ran away with the boarding party - one lieutenant, one bos'n and thirteen seamen - and only upon their pleas did I heave to and put them back on the Seneca. The damned radio was too severe a handicap for me. I surrendered after the Seneca had fired four-inch shells at me.
When asked what defense he planned to make at the hearing before the trial, McCoy introduced the details of his operations by replying:
I have no tale of woe to tell you. I was outside the three-mile limit, selling whisky, and good whisky, to anyone and everyone who wanted to buy.
Instead of a long drawn out trial, Bill McCoy pleaded guilty and spent nine months in a New Jersey jail. He returned to Florida and invested his money in real estate. He and his brother continued the boat building business and frequently traveled up and down the coast.
![](https://photos.metrojacksonville.com/photos/1519268490_bqbLCsn-M.jpg)
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McCoy, in his autobiography, entitled The Real McCoy, explains what drew him into this illegal trade. "I went" he says, into rum running "for the cash and I stayed in it for four years for the fun it gave me." In those years he made hundreds of thousands of dollars, and by the time he was arrested he had personally delivered more than 700,000 cases of liquor to the U.S. He wrote, "there was money in the game -- lots of it if you could keep it. Beyond that there was all the kick of gambling and the thrill of sport, and besides these, there was open sea and the boom of the wind against full sails, dawn coming out of the ocean, and nights under rocking stars. These caught and held me most of all."https://www.oceannavigator.com/content/smuggler-kicks-st-pierre-boom
The Liquor Czar: The Whiskey King of Duval County on next page.
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.
![](https://photos.metrojacksonville.com/photos/1519291196_Jd2mHkw-M.jpg)
John Hysler was gunned down during a moonshine run on the Acosta Bridge in 1928.
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"You mean you really have not heard about what happened to John Hysler today?"https://www.storymania.com/cgibin/sm2/smreadtitle.cgi?action=display&file=nonfiction/ClementD-StormyPetrels.htm
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 there...as pallbearers.
![](https://photos.metrojacksonville.com/photos/1519323593_xMbjms6-M.jpg)
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.
![](https://photos.metrojacksonville.com/photos/1519389356_6r7NLQ9-M.jpg)
Image courtesy of https://www.cowart.info/blog/?m=200712&paged=2
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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.https://www.cowart.info/blog/?m=200712&paged=2
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.
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.
![](https://photos.metrojacksonville.com/photos/1519268451_3cD58Pq-M.jpg)
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.
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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.https://www.historicpalmbeach.com/tag/ashley-gang/
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.
https://history.jupiter.fl.us/History/Ashley_Gang.cfm
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.
The Whisper Sisters on Next page
The Whisper Sisters
During Prohibition, Jacksonville was a major port of entry and manufacturing center for hooch. It was a very easy way to turn $200 into $2,000, according to one North Florida still operator. What is not known is that for every male in the business, there was an opportunistic female to meet his match. It can be argued that the Whisper Sisters were the best.
Quote
Virtually impossible to apprehend, the Whisper Sisters brewed beer in private dwellings, often renting fashionable apartments solely for that purpose. The Times-Union said the Whisper Sisters made "quite good" beer, the reporters having a professional obligation to find out for themselves.Source: The Florida-Times Union archives
Nobody could get into the apartments without a search warrant, the agents complained. The law protects many a dwelling that shelters a flagrant violator of the Volstead Act," the Times-Union said.
Lyndall McMurray
You can't have a story about Prohibition and not mention Springfield, one of Jacksonville's most colorful historic neighborhoods. In 1926, Mrs. Lyndall McMurray became a Prohibition-era celebrity among First Coast women. Mrs. McMurray was known to sell soda pop in front of a Main Street tent, and hooch out the back. It was said she shot her man to death on a Springfield street because he mistreated her after she stole ten cases of whiskey from him. She was found not guilty in front of a courtroom packed with women.
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Mrs. Lyndall McMurray, Who Shot Mail Carrier 'to Save Son And Self,' Not Guiltyhttps://news.google.com/newspapers?nid=950&dat=19260819&id=z5sLAAAAIBAJ&sjid=lVQDAAAAIBAJ&pg=2143,429981
Jacksonville, August 19-(AP)_ Mrs. Lyndall McMurray, alias Born, charged with the slaying here in June of Adolphus S. Ward, rural mail carrier, was found "not guilty" in circuit court late yesterday. The jury was out in 40 minutes.
Ward was shot on a residential street June 13. He died a week later in a local hospital. Mrs. McMurray testified during the trial that she shot at Ward to protect her 14-year-old son, John, as well as herself. Mrs. McMurray was taken into custody at Nashville, Tenn., several days after the shooting. She was the first white woman tried for murder in court here in a number of years.
Sheriff W.H. "Ham" Dowling
Ham Dowling was a man who thought he was above the law. Dowling, a former SAL train conductor and son of a Baptist minister, was elected Duval County sheriff in 1912 on a strong law-and-order campaign against "a carnival of crime." In 1917, Governor Sidney Catts suspended him for lax enforcement of anti-liquor laws but he was reinstated a few months later. Five years later, he was suspended by Governor Cary Hardee on a conspiracy charge but was later reinstated. In 1928, W.B. Cahoon was elected over the long-time sheriff and commenced bare-knuckle law enforcement that Jacksonville had not seen during most of the Prohibition era under Dowling.
Not surprisingly, two years later Dowling was in the news again. This time for being busted for the ownership of two stills with 14,000 gallons of beer, 250 gallons of whiskey and 79 bottles of home brew. Dowling ended up being sentenced in 1931 to two years in a federal prison in Atlanta.
Source: https://jacksonville.com/tu-online/stories/062099/met_2b1Foley.html
![](https://photos.metrojacksonville.com/photos/1519268505_QkgDpq3-M.jpg)
A 1930s-era moonshine still busted by Sheriff W.B. Cahoon. Below, Sheriff W.B. Cahoon destroys a downtown still.
![](https://photos.metrojacksonville.com/photos/1519334014_xWmTr2N-M.jpg)
Sheriff W.B. Cahoon images courtesy of the State Archives of Florida.
Dowling wasn't the only public official busted during prohibition. Practically the entire South Jacksonville city administration, including the mayor, the chief of police, the president of the city council, the city commissioner, and the fire chief, were indicted by a federal grand jury as well.
Source: https://www2.potsdam.edu/hansondj/Controversies/1091124904_6.html
Henry "Skimp" Tillman
Skimp Tillman was one of the most notorious one-eyed barkeeps in Jacksonville during the 1930s. Tillman was known to use fists, guns and knives to settle disputes in downtown Jacksonville. Over a course of 20 years, he had been charged with assault to murder, to protect his well being six times, including shooting a customer to death in 1935. Skimp's luck of getting away with murder would end with the Court of Circuit Judge Bryan Simpson in 1948, after the shooting death of another customer.
![](https://photos.metrojacksonville.com/photos/1519291202_nCKRDBg-M.jpg)
Inside Jimmy Mains bar in 1933.
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The appellant-defendant, Henry V. (Skimp) Tillman, was indicted in the Circuit Court of Duval County, Florida, for the murder of Frank E. Wood. Shortly thereafter he was placed upon trial in the same court and a jury, after hearing all the testimony, returned a verdict of murder in the first degree, without recommendation as to mercy. The trial court denied defendant's motion for a new trial and the death sentence was imposed. The defendant appealed. It appears that Frank E. Wood was shot at the corner of State and Main Streets in the City of Jacksonville about 2:30 p.m., August 12, 1948, and languished until November 28, 1948, and died. Wood lived three months and sixteen days after the appellant-defendant shot hom.https://fl.findacase.com/research/wfrmDocViewer.aspx/xq/fac.19500207_0040150.FL.htm/qx
The record discloses that the appellant operated a bar on August 12, 1948, situated at the northwest corner of Main and State Streets in Jacksonville, Florida, and the deceased and his brother, Edmund Wood, went to the saloon for a drink of beer and when there were served by the appellant. A conversation ensued between the two Wood boys and the appellant about some criminal cases of county-wide interest previously tried in Duval County, to wit: the Hyslers, Melvin or Smitty cases. It appears that a fight occurred between Frank E. Wood, the deceased, and the appellant-defendant, during which the appellant shot Wood in the shoulder and the pistol ball ranged backward severing his spinal cord. The shot rendered Wood immediately helpless and he fell to the floor, as his body below the place of severance of the spinal cord was paralyzed.
https://jacksonville.com/tu-online/stories/061000/nef_3257700.html
After being found guilty of first-degree murder, Skimp Tillman was electrocuted on June 5, 1949.
William Ostner: Father of the Six Pack
What would a Prohibition-era story be without mentioning the brewmaster who brought a full-scale brewery to town? Jax Beer was said to be the beer of the common man and the woman who smoked menthols, of the bon-vivant in a blue collar and the siren in Evening in Paris.
This brewery's start dates back to Moncrief Park, a full decade before Prohibition. In 1910, Moncrief Park's horse racing track drew spectators from all over the country. One of those spectators was William Ostner, a German-born brewmaster living in St. Louis.
![](https://photos.metrojacksonville.com/photos/1519350737_3rzSMK8-M.jpg)
The Jax Brewing Company facilities in 1959. Image courtesy of www.beercanhistory.com
Soon, Ostner would move to Jacksonville and set up the Jax Brewery Company on 16th Street, only to see the racetrack close and Prohibition enacted. During Prohibition, the company's name would change to Jax Cold Storage Company. In 1933, a week after the repeal of Prohibition, brews were rolling off the production line once again. After World War II, the Ostners bought 100,000 durable stacks from Towers Hardware, emblazoned Jax Beer on them, and sold beer six to a sack, and the concept of the six-pack is history. In 1957, the company was sold to Jax Brewing of New Orleans and the plant was converted into a major cold storage warehouse.
Article by Ennis Davis.