Florida Once Upon a Time… Prohibition, Rum-Runners and Shady Characters

Words by Ted Hunt


The 18th Amendment to the United States Constitution prohibiting the manufacture, sale or transportation of intoxicating liquors was ratified in 1919 and went into effect in January of 1920. The often-called Prohibition Amendment, aimed at curbing alcohol consumption, forced the closing of hundreds of breweries and put an end to thousands of saloons across the nation. However, it had the unintended consequence of fueling a thriving, and illegal underground industry.  


Despite the law, millions of Americans chose to drink anyway, so the demand for booze had to be satisfied through illegal means. There was rum running, bootlegging, speakeasies and moonshining. It was also the beginnings of organized crime — Al Capone, Frank Costello and of course “The Godfather.”


Rum-running was the smuggling of rum, whiskey, scotch, champagne and other liquors by sea. The famous Florida drink called the rum runner was named after those smugglers — but more on that later.


Bootlegging was the illegal manufacture, distribution or sale of alcohol. Distribution included the transportation of liquor by trucks and souped-up cars carrying cases of booze, flying down dirt roads, being chased by the cops. Bootlegging even gave rise to the birth of auto racing: Today known as NASCAR.


Speakeasies were the illegal bars that served the outlawed booze. Moonshiners were the hillbillies in the woods that distilled 100 + proof corn-liquor and served it in mason jars, often by the light of the moon … Get it?


The Right Place at the Right Time

Florida was strategically positioned to capitalize on the ban on alcohol. The state’s proximity to the Bahamas and Cuba, where liquor flowed freely, made it a prime location for smuggling operations. Florida’s coastline became a hotbed of illegal activity, earning the state a notorious reputation for its rum runners and bootleggers. A case of Cuban rum that cost $4 in Cuba, would bring $100 when it reached Florida’s shores and $500 in cities like New York and Chicago. Many rum runners watered down their alcohol or re-labeled bottles of cheap booze as more expensive brands to make it more profitable. It was a dangerous business and there was big money to be made — If you didn’t lose your life first!  


Rum runners would load up their schooners, yachts, speedboats and fishing boats with cases of liquor and run nightly trips from Bimini, Nassau and Cuba to Florida’s coast. Bimini, only 50 miles from Florida, built nine liquor warehouses and had over 50 powerboats that could reach the Florida coastline in two hours. The boats had an extensive shoreline of secluded inlets, coves, mangrove swamps and remote lagoons to choose from.


These coastline entry points all provided ideal hiding spots and escape routes, making it nearly impossible for law enforcement to intercept them. Bootleggers would meet the boats, offload the cases onto trucks and cars that would quickly head north with their precious cargo.


In the early 1920s the United States jurisdiction over its waters was limited to three miles out from the coastline. Outside this three-mile line were international waters. The Coast Guard was responsible for patrolling the Florida three-mile limit and the enforcement of Prohibition. The Coast Guard’s fleet was very small and not prepared to cover such a large area. The rum runners took full advantage of this lack of coverage. Under the cover of darkness, the runners in the Bahamas would load large boats with cases of booze, go to the three-mile line and form a long row and wait for smaller boats from Florida and transfer the cases. Many would post signs on their boats listing the names and prices of their liquors. The smaller boats would then speed off toward Florida to meet the bootleggers. The larger boats would go back to Nassau and repeat the cycle. This area was called Rum Row: It was just too easy.  


Shady Characters

The rum runners were a motley crew of gangsters, thieves and crooks. There was Bill McCoy who ran a successful operation along the entire east coast of Florida. He worked both sides of Rum Row. On one of his boats, he had a large concealed machine gun used to keep other shady characters from stealing his illegal booze. His reputation was for selling only high-quality, not watered-down liquor. He amassed a fortune, was eventually caught, served time in prison, was released and then retired, with his fortune, near Stuart, Florida. His name gave birth to the phrase “the Real McCoy” – for “the real stuff.”


The notorious Ashley Gang was a band of Florida east coast locals who ran booze between the islands and the states. Known as Florida’s notorious Jessie James Gang, they robbed banks, stagecoaches and trains. They were also rum runners, bootleggers and moonshiners. The members died in 1924 after a police chase in Sebastian, Florida.


Not all rum runners were men. There was Spanish Marie, also known as Havana Kitty to the US Coast Guard. She had a fleet of four large boats and 15 speedboats to move her liquor between Havana, Cuba and the Florida Keys. She was known for her ability to out maneuver the Coast Guard. She would strut around her crews with a revolver strapped to her waist and a large knife tucked in her belt. Everyone knew she was the boss. By 1927 she was the industry’s undisputed leader and rumored to have racked up over $1 million during her reign. She was nabbed in Miami in 1928, posted bail and vanished with all of her children and money — never to be seen again.


Then there was Cleo, the Queen of Rum Row. Named after the beautiful Egyptian queen Cleopatra, she set up a liquor smuggling business in Nassau, Bahamas providing booze to the Florida coast. She was well liked for her business acumen and hard-nosed attitude.  She made up her own rules, and if you crossed her, she could be ruthless. It’s rumored that she treated her enemies and men like well-tanned praying mantises. She acquired vast sums of cash for her efforts. She bought gowns in Paris and jewels the size of hen’s eggs. Fearing for her life she retired from the business in 1926 and spent her time between Detroit and Los Angeles. When she died, Nassau flew their flags at half-mast for days in honor of their fallen queen.


The Sinking Ship

The United States extended the three-mile limit to 12 miles in 1924 which made it difficult for smaller and less seaworthy craft to make the trip from Florida to Rum Row. In 1926, the Coast Guard also added additional and faster ships to its fleet forcing many runners to dump their liquor into the ocean to avoid arrest. Florida police departments added additional officers that staked out inlets, docks and boathouses and began to stop and inspect every boat. Through their efforts, many rum runners and bootleggers were arrested. In 1927, the United States Supreme Court ruled that American-flagged ships with illegal liquor could be seized up to 34 miles from shore. This was a major blow to the industry. Rum Row had been put out of business, and the rum runners quickly began to fade into history.


Stateside, organized crime which was heavily invested in bootlegging was bribing businesses, political leaders and entire police departments, effectively crippling the ability to enforce the Eighteenth Amendment. By the 1930s, the corruption caused by Prohibition, the Great Depression and the resulting need for jobs and tax revenue caused public sentiment toward Prohibition to flip and Congress was compelled to act. Prohibition came to an end with the ratification of the 21st Amendment in 1933, legalizing the sale and consumption of alcohol. It remains the first and only time in history that a Constitutional amendment repealed a previous Amendment — America could once again raise a glass of legal alcohol in toast.


Speaking of toasts … staying close to its namesake, the rum runner drink was concocted in a Tiki Bar in Islamorada, Florida, which is only fitting since Islamorada was one of Havana Kitty’s favorite haunts. The drink includes Havana light and dark rums, banana and blackberry liqueur, orange and pineapple juices, and grenadine. 


So cheers to the 21st Amendment!

About Ted Hunt