Bootlegging stories from Prohibition tell of some pretty elaborate and colorful schemes by criminals. Smuggling alcohol through customs, making bathtub gin, adopting religious pseudonyms for sacramental wine, and sailing out to Rum Row are just some of the stories that have become Americana. They were breaking what many interpreted as an unjust law. How un-American was it to ban alcohol? How dare some politicians close down the Jack Daniels and Jim Beam distilleries? Or iconic brewers such as Anheuser-Busch, Schlitz, and Pabst? The scofflaws who flouted the 18th Amendment and Volstead Act believed they were battling against tyranny by drinking and bringing alcohol to their customers.

Bootlegging operations ran all over the Western Hemisphere; from Canada all the way down to Central and South America. Gangsters from infamous crime families to families making home-brewed beer subverted Prohibition for different reasons and contemporary historians investigate the morality involved in all types of bootleggers. Many of them cut corners by thinning alcohol with industrial chemicals or herbal concoctions that could make them downright deadly. When a person bought beer or distilled spirits from a bootlegger, they were potentially risking their lives.

William S. McCoy, captain of the schooners Tomoka and Henry L. Marshall. William and Benjamin (not pictured) ran rum-running operations along the Eastern Seaboard for about four years until they were finally apprehended by the U.S Coast Guard (photo courtesy of the U.S. Coast Guard)

A sea captain with a heroic, folklore reputation rose above the blanket categorization of bootlegger. He prided himself on never having worked with organized crime or watering down and polluting his alcohol with adulterants. William McCoy, and his brother Benjamin, were partners in a smuggling operation that ran from the Caribbean all the way up the Eastern Seaboard of the United States. Bootlegging to William McCoy was his way of being an ‘honest lawbreaker’. He found inspiration with John Hancock, the Founding Father whose shipping business was at the center of questioning unfair British taxes and smuggling in the American colonies. William and Benjamin gained a reputation in the early 1910s as skilled craftsmen and boat builders in Florida. They ran a small motor boat service and shipyard, but at the start of Prohibition in 1920, the McCoy family fell on hard times. Boat freights were slowly replaced with the growing trucking industry and the brothers stood at a crossroads. What could they do to earn a living? How could they use their skills to earn money in this new environment? The answer came easily: rum-running.

Drawing on his maritime knowledge and experience as a sea captain, McCoy shipped vast quantities of alcohol from Caribbean islands (the Bahamas and Bimini primarily) up through shipping lanes to Florida. Buyers flooded McCoy with purchase orders to fill demands in the southern United States. In just one trip, McCoy generated enough profit to pay off the main business expense, his schooner the Henry L. Marshall. McCoy expanded the rum-running venture to purchase six more vessels, including the Tomoka which he registered under British customs to divert suspicion from the U.S. Coast Guard. McCoy further avoided capture from authorities by pioneering an idea of having barges and freighters filled with product anchored at least three miles offshore in international waters. The floating alcohol wholesalers became known colloquially as ‘Rum Row’. Credit for this idea has historically gone to McCoy, according to both family records and the U.S. authorities. By completing business deals at sea, customers could purchase orders and when ready for pickup, they were outside U.S. jurisdiction. For three years, from 1920 to 1923, McCoy routinely pocketed anywhere from $50,000 to $100,00 per delivery (approx. $600,000 to $1,000,000 dollars today). The brothers’ run came to end on November 23, 1923 when the U.S. Coast Guard cutter Seneca tracked the Tomoka into international waters and apprehended the brothers. William McCoy was charged with multiple violations of the Volstead Act and rather than taking his case to trial, McCoy plead guilty to the charges and spent nine months in a New Jersey jail and paid a large fine. Despite having lost the profitable rum-running venture and his ships confiscated by the Coast Guard, the McCoys amassed a considerable fortune that they later put back into their boat building business and into the booming Florida real estate market.

Rum Row brought alcohol straight from the international market. Buyers could purchase anything from blended whisky and rum to the finest wines and champagnes (photo courtesy of the U.S. Coast Guard)

Unlike other bootleggers and rum-runners, the McCoy brothers took measures to deliver the best product to their clients. They never engaged in diluting their alcohol or cutting it with dangerous substances. Business with organized crime figures was never conducted and they even paid their crews more than other rum running outfits to keep them from stealing product. The rum running business was a game-changer for the Bahamian economy. Exploding alcohol sales and increase in alcohol tourism at the time made the Bahamas a vacation hot spot. This was due large in part to Prohibition and the scores of rum runners who bought their product overseas and sold it in international waters. Despite numerous complaints by the U.S. government, the British Foreign Office never intervened in the rum running operations. But Prohibition is not without its darker narratives as is the case with all history.  Alcohol statistics during the Prohibition are, in the best definition, paradoxical. Production, sale, distribution, and consumption of alcohol was down and alcohol related crimes such as driving under the influence and public intoxication was down in some regions. On the contrary, that same data showed an exponential increase in other regions; so much that even stricter legislation was passed to crack down on abusers (e.g. New York’s Mullan-Gage Law). Prohibition crafted the national crime syndicates between crime families and in the law’s attempt to ban alcohol, the number of alcohol related fatalities exploded overnight. These were times where people really went off the deep end.

Researching the history of Prohibition without incorporating William McCoy is akin to discussing the Constitutional Convention and not mentioning Alexander Hamilton or James Madison. McCoy’s rum running career gained a folklore status in the U.S. and his story stands out among bootleggers for his aversion to violence and retiring early to capitalize on his adventurous gains.