Bootlegging and Rum-Running in Jacksonville

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.

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.

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.

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.