Whiskey on the water

The intrepid booze buccaneers of yore


In 1920, America went dry. The work of temperance movements such as the Anti-Saloon League had finally paid off, and it was illegal to make, sell, and distribute alcohol in the United States. Remarkably, consuming it was not technically illegal, and the 18th Amendment certainly did not stop people from wanting to drink rum, whiskey, gin, and other types of alcohol. During Prohibition, alcohol made by amateur distillers was in circulation. Drinks like moonshine and bathtub gin were standing in for the professionally produced spirits that the country had grown accustomed to before Prohibition. These homemade spirits, available in speakeasies across the country, were frequently strong, and often not particularly pleasant. Moreover, some of these spirits were dangerous. In some cases, they were made from industrial grain alcohol, denatured with chemicals. According to The Mob Museum, as many as 50,000 drinkers died from consuming tainted alcohol during Prohibition. Those who wanted a dram of something decent – and safe – needed to source it from elsewhere. Getting it in the country from overseas would be the tricky part. It was a job for the seafaring bootleggers known as the Rum Runners. 

During Prohibition, rum running was the practice of smuggling liquor into the United States. Rum from the Caribbean and whiskey from the UK was loaded onto boats, which carried the goods to the edge of international waters. Then, smaller boats, sometimes called contact boats, would travel across territorial waters, from the shoreline to the rum runner’s vessel, and collect the liquor to be taken to shore. Before long, ‘Rum Row’ stretched along the eastern seaboard, and throughout the 1920s, it was a profitable business. Naturally, it was also a dangerous one, and rum runners had to get creative to avoid getting caught. For example, false bottoms helped to keep the liquor out of sight in the hull of the boat.

Among the most famous of the run runners was Bill McCoy, a former merchant sailor and boat builder. Whilst he didn’t drink alcohol himself, he was more than happy to help Americans access the quality booze that they desired, for a price. McCoy needed a boat that he could rely on to make his business a success. He chose a fishing schooner called the Henry L. Marshall, which needed a bit of work. Soon, he had his eye on an even bigger and better boat. But first, he needed to make some money from selling liquor. 

The Coast Guard’s workhorses for Prohibition enforcement were 75-foot patrol boats such as these New London-based vessels, seen in 1927. Among them is CG-290, which was later involved in the Black Duck incident © U.S. Coast Guard

In his first trip, McCoy netted profits of $15,000, dwarfing his prior earnings as a boat builder. McCoy was fast to learn that it would be safest to remain three miles from the shoreline, as this was the distance that the United States territorial waters stretched to. The small contact boats that collected the bottles of whiskey or rum from McCoy’s boat were fast enough to avoid contact with the Coast Guard. It was, seemingly, a fool proof business model, and one that McCoy excelled at. Some say that he gives his name to the common saying ‘the real McCoy’, because the booze he sold was the real deal: quality spirits which were never watered down. He had a good reputation, was known for his reliability and fair pricing, and was easy to do business with, which built trust with a loyal customer base. With business booming, McCoy could expand his fleet, and finally, he could acquire his dream boat, the Arethusa, which he renamed the Tomoka.

Though McCoy was arguably the most prolific of the Rum Runners, the demand for quality alcohol was large enough to sustain many other players. Another of the rum runners was Gertrude Lythgoe, who was nicknamed ‘Cleo’. “By 1923, Cleo Lythgoe was selling millions of gallons of whiskey a year,” writes Mallory O’Meara in her book Girly Drinks. Hungry for more business, Lythgoe partnered with McCoy. They operated out of Nassau in the Bahamas, which at the time was part of the British Empire. As well as avoiding the Coast Guard, the most successful bootleggers of the era had to protect their stash of booze from other bootleggers. “Hijacking among smugglers was commonplace,” O’Meara writes. “For her own peace of mind, Cleo was never without her huge pistol.”

Another well-known bootlegger in the era was Roy Olmstead, who still worked in the Seattle Police Department when he first began importing liquor from Canada. Though the Pacific coast’s Rum Row never ballooned to the size of that on the Atlantic coast, there was still an opportunity for bootleggers, and Olmstead was the man to take advantage of it. “Roy Olmstead was handsome, personable, intelligent, and remarkably ethical,” writes Daniel Okrent in his book Last Call: The Rise and Fall of Prohibition, adding that Olmstead dealt in high volumes which enabled him to undersell the other bootleggers in the Pacific Northwest.

Gertrude Lythgoe

The Coast Guard, which was officially so named when the Revenue Cutter Service merged with the U.S Life Saving Service in 1915, needed to up their game to fight the war against the Rum Runners, but it was not an easy battle to win. Waiting for funding from the government for extra boats and personnel meant that the Coast Guard were always a few steps behind the bootleggers of Rum Row, who could adapt in a more expedient and agile manner. In some cases, boats were fitted with airplane engines to help them be speedier and more efficient at outrunning the Coast Guard. Despite their challenges, the Coast Guard did manage to seize vessels, and eventually, time was up for the pioneer of the rum running business. In November 1923, the Coast Guard cutter Seneca captured Bill McCoy’s boat, the Tomoka. McCoy later pled guilty to smuggling and served a nine-month prison sentence. 

Catching McCoy was about more than shutting down his operation alone; it was about the broader victory against the bootleggers of Rum Row. Enforcing compliance with the law was a priority, and warning shots were often fired by the Coast Guard. The effort to stay tough on crime took them into murky waters in 1929, when an officer onboard a Coast Guard patrol boat fired on a motorboat called Black Duck, and three men on board the boat were killed. The Coast Guard maintained that it had not been their intent. There was an inquiry into the incident, and the Coast Guard boatswain in question was exonerated. Nevertheless, the event caused public outrage. It was becoming clear to many that the Volstead Act wasn’t effective. 

In 1933, Prohibition ended, meaning the end of the so-called Rum War, but the memory of the period’s most notorious bootleggers and rum runners lives on. The likes of McCoy, Lythgoe, and Olmstead will be remembered for getting the better of the Coast Guard to deliver top quality booze to their loyal customers. Were they heroes or villains? That is simply a matter of perspective.

Cover photos: © U.S. Coast Guard

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