The Real McCoy: The Rum-Runner Who Outsailed Prohibition
- dthholland
- 1 minute ago
- 6 min read
In the roaring tide of Prohibition, when the United States tried to legislate temperance and wound up inspiring a decade-long national thirst, a few bold spirits answered the call of opportunity. One of the most audacious, and arguably the most honest, was a tall, sea-weathered man named William Frederick “Bill” McCoy. His name would become a byword for quality and authenticity. In the chaotic world of illegal liquor, The Real McCoy stood out, not just as a daring smuggler, but as a man who broke the law with a peculiar sense of honour.
Bill McCoy: From Wharves to the High Seas
Born on 17 August 1877 in Syracuse, New York, Bill McCoy’s life seemed destined for the water. The son of a Scottish-American bricklayer who had served in the Union Navy during the American Civil War, McCoy was captivated by maritime tales from an early age. As a teenager growing up in Philadelphia, he spent his days hanging around the Delaware River docks, dreaming of a life at sea.
One afternoon, he caught sight of the Saratoga, a Philadelphia Maritime School training ship. That was it. He informed his father that he would not be following in the family trade of bricklaying. After two years of rigorous training aboard the Saratoga, McCoy graduated first in his class. He quickly rose through the ranks, earning $75 a week as a mate aboard steamers running between Key West and Havana, a substantial salary at the time.
Around 1900, the McCoy family relocated to Florida. Bill and his elder brother Ben set up a boatbuilding and motor service, catering to an illustrious clientele that included the Vanderbilts, John Wanamaker, Maxine Elliott, and Andrew Carnegie. They even operated an ambitious boat service from Jacksonville to Palm Beach, winding south through the Everglades to Fort Myers.
By 1918, McCoy was well-established as a master yacht builder. But the looming shadow of Prohibition and post-war depression was about to change everything.
Setting the Stage: Prohibition and New Beginnings
In January 1920, the National Prohibition Act came into effect, banning intoxicating beverages across the United States. The post-World War I economy faltered, luxury yacht commissions dried up, and life turned bleak for the McCoy brothers. Amid these hard times, Bill suffered a double blow: the death of both his parents and the collapse of his brief marriage to a prominent Daytona surgeon’s daughter.
At 42 years old, McCoy found himself at a crossroads. That was when fate intervened in the form of a dapper stranger behind the wheel of a gleaming motorcar. Over casual conversation, McCoy learned that America was practically begging for liquor — and there was an enormous fortune waiting for anyone willing to ferry it from the Bahamas to the U.S. East Coast. All they needed were schooner captains.
Though initially sceptical, the idea took root. Adventure, cash, and a return to the open water? It was irresistible.
Enter the Arethusa (Later the Tomoka)
In August 1920, McCoy cobbled together $20,000 and travelled to Gloucester, Massachusetts, in search of a ship. That was where he first laid eyes on the Arethusa. She glided into the harbour like a queen, sails blazing gold in the sun. McCoy was entranced. “She seemed to ghost into the harbour’s mouth under full sail… My throat was tight and stiff as she came walking up the harbour like a great lady entering a room,” he later recalled.
Unable to afford her at first, McCoy bought a sturdy 90-foot fishing schooner, the Henry L. Marshall, for $16,000. Registered under a British flag for legal protection, he quickly made his first successful run to Nassau, clearing a tidy $15,000. A few months and a $35,000 profit later, McCoy returned to Gloucester to purchase his dream vessel. Renamed Tomoka to avoid conflicts with British registry, the Arethusa was outfitted for speed and cargo. She could now carry up to 5,000 cases of whisky — a cargo worth $50,000 a trip.
McCoy was officially in the game.
Rum-Running with Honour
Bill McCoy’s operations quickly distinguished themselves from the sordid chaos that often marked Prohibition-era smuggling. Anchoring just outside the three-mile limit off New Jersey, McCoy turned the Tomoka into a floating liquor store, selling whisky, rum, and champagne to contact boats that darted out from the shore.
And he did it his way. McCoy refused to deal with organised crime, refused to bribe politicians or law enforcement, and sold only unadulterated, high-quality liquor. His innovation, the “burlock” — six bottles bundled tightly in straw and burlap — made transporting liquor faster and safer.
Soon, he commanded a fleet of five vessels and moved an estimated two million bottles over his career. His brother Ben ensured the Tomoka remained supplied with food, water, and newspapers, allowing her to stay offshore indefinitely. When McCoy’s ship flew no flag, it signalled to the contact boats that she was open for business; a bright light hoisted high in the rigging became a beacon for eager buyers.
Old Faithful, McCoy’s Newfoundland dog, was a constant companion. Fiercely loyal, Old Faithful once swam ashore and slept under McCoy’s hotel window all night in Bermuda. On board, the dog famously guarded an unlocked drawer sometimes containing up to $100,000 in cash.
Fame, Fortune — and Fallout
As rum row grew into a floating city of smugglers, jazz bands, and enterprising captains, McCoy became the king of it all. His fame spread like wildfire. Newspapers painted him as a modern pirate with a heart of gold, a folk hero for an America fed up with Prohibition.
However, the U.S. government saw him differently. To Washington officials, McCoy was a symbol of lawlessness that needed to be crushed. Federal funds were allocated to double the size of the Coast Guard fleet, and enforcement on the high seas intensified.
In the summer of 1923, McCoy’s original ship, the Henry L. Marshall, was seized under dubious circumstances. The government argued that even being within reach of contact boats was grounds for prosecution. A nervous rum row watched as the legal loopholes began to close.
The Capture of Bill McCoy
In November 1923, the Coast Guard Cutter Seneca approached the Tomoka under orders to bring McCoy in, even in international waters. After a tense standoff involving machine-gun fire and four-inch shells, McCoy surrendered. Ever pragmatic, he paid his crew their wages one by one as the captured Arethusa (to him, she would always be the Arethusa) was towed towards New Jersey.
Awaiting trial in Newark, McCoy became the focus of public fascination. Pete Sullivan, a customs agent McCoy had once saved in Nassau, testified on his behalf. McCoy was even paraded around Washington, D.C., shaking hands with awe-struck congressmen and federal agents.
The courthouse hearing was packed as the tall, well-dressed McCoy rose to address the Newark judge. Reporters leaned forward, pens poised. The judge cleared his throat and asked what defence McCoy intended to mount. In a soft, steady voice, McCoy replied:
“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.”
With his March 1925 guilty plea, the grand saga of Bill McCoy, anti-Prohibitionist hero, came to a close.
Life After the Rum Wars
McCoy served just nine months in jail, enjoying many privileges, including attending boxing matches while incarcerated. Released on Christmas Day 1925, he returned to Florida to live modestly with his brother.
Although his beloved Arethusa was eventually wrecked off Halifax, parts of her — her wheel, her lines — remain enshrined in American maritime museums.
Bill McCoy continued working in boatbuilding and real estate until his death on 30 December 1948, aged 71. His legacy remains that of a man who brought dignity, professionalism, and a touch of romance to one of America’s most colourful periods of lawbreaking.
Even today, when people speak of something being “The Real McCoy,” they unknowingly pay tribute to a fearless captain who defied Prohibition, and did it with style.
