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The Roaring Twenties was a time of great social, cultural and economic change. A new society had emerged, one no longer bound by the restrictive morals that once dominated the Victorian era, or by the hardships endured during World War I. People wanted to have a good time, and they did.

When the 18th Amendment was passed in 1919, prohibiting the production, sale and transport of alcohol, and enforced by the Volstead Act of 1920, many Americans feared it might be the end of their all-night shenanigans. However, the fun and games were just beginning. The thrill of sneaking a drink and making an unlawful purchase was exhilarating, and the demand for alcohol remained strong as ever, necessitating new suppliers. Thus, out of Prohibition came the rum-running era.

The infamous Arethusa crew loads a shipment of scotch onto a seaplane.

The infamous Arethusa crew loads a shipment of scotch onto a seaplane.

Located nearby several inlets and waterways that eventually empty into the Atlantic Ocean, Freeport, New York, was an ideal place for the illicit smuggling of spirits. Freeport was more accessible than the Hamptons with its trains, trolleys and paved roads, and it became a summer hotspot for Manhattanites seeking to escape the heat. There was an amusement park that rivaled Coney Island, and the area was riddled with hotels, bars, brothels and theatrical clubs where celebrities like Guy Lombardo, Harpo Marx and Jimmy Durante performed. These establishments relied on a constant infusion of alcohol.

Agents surrounded by cases of alcohol in the hold of an impounded ship.

Agents surrounded by cases of alcohol in the hold of an impounded ship.

A fishing fleet also thrived in Freeport, and many baymen became involved in rum running as a way to supplement their income, especially during the Depression. Most acted as middlemen, running booze for a syndicate, trucking business or speakeasy owner. It was a natural evolution. They had the vessels, boat-handling experience and knowledge of the local waterways that businessmen did not possess. Additionally, Freeport’s inlets and beaches provided perfect cover. The boats could be beached at will, and the liquor offloaded onto a desolate stretch of land for later collection.

“Prohibition took place over the course of 12 years, but in the early 1920s it was really a mom-and-pop operation,” says Dr. William Theisen, Atlantic area historian for the U.S. Coast Guard. “Anyone who wanted to make a little extra could operate on the side.”

Lt. L.W. Perkins firing at a fleeing rum-running crew.

Lt. L.W. Perkins firing at a fleeing rum-running crew.

Schooners and small coastal vessels imported the booze from Canada, Europe and the Bahamas, anchoring offshore from New York City to Montauk Point. This 100-mile stretch became known as Rum Row. But buying booze was risky business. Not only was it illegal, but it was not uncommon to purchase rancid hooch or to overpay. The Arethusa, a schooner owned by Bill McCoy, had a reputation for having the finest liquor at the fairest prices. The widely known expression “The Real McCoy” was coined during this period when rumrunners went in search of the Arethusa to ensure they were getting the best product.

Rum-running ships were essentially one big floating supermarket with liquor as the only commodity. As long as the motherships remained 3 miles from shore, they were technically in international waters and untouchable by the Coast Guard. (Later, the limit was increased to 12 miles.) The Coast Guard as we know it today was born out of this era. The Coast Guard was barely five years old when the federal government ordered it to break up the trade.

If Johnny Law was close behind, rumrunners might ditch the goods and try to retrieve them after getting away. 

If Johnny Law was close behind, rumrunners might ditch the goods and try to retrieve them after getting away. 

“The Coast Guard did not have the patrol boats, watercraft or ships to handle the volume of liquor being smuggled in by water. They had to build a flotilla of small craft picket boats,” says Theisen. “Prohibition was the largest law enforcement mission to date in terms of building a fleet for interdiction purposes. I don’t believe there was another time in [Coast Guard] history that [the Armed Forces branch] grew as quickly as it did then.”

The Coast Guard vessels were often built by the same yards that built the rumrunner ships. Frederick Scopinich, age 94, was just a boy at the time but remembers the stories his mother told him about his father’s boatyard, Freeport Point.

Agents examining barrels on the deck of a ship.

Agents examining barrels on the deck of a ship.

“Freeport Point was commissioned by the Coast Guard to build 10 patrol boats. But because they had to adhere to certain specifications, their boats could never be built to go as fast as the rumrunners. The rumrunners had high-powered Liberty aircraft engines installed in them left over from World War I and traveled about 35 mph. The Coast Guard boats only went 24 mph,” says Scopinich.

Because many rumrunners were also local fisherman who knew the waterways, they often eluded apprehension. The Coast Guard also had the disadvantage of having to identify themselves before making a capture. Once the rumrunners were informed they were about to be arrested, they pitched the evidence overboard. But they were no dummies—they had clever ways to retrieve the “lost” goods. One way was wrapping the bottles in bags filled with just enough salt to sink them, and just enough cork to recover them. Once the salt melted, the cork floated the bags to the surface. Another method was to place a flashlight inside a glass jug and weigh it down with a rock. The flashlight cast a dim glow underneath the sea so they could find the goods later.

Fishermen from Chicago’s Fulton Market ferry loads back to shore.

Fishermen from Chicago’s Fulton Market ferry loads back to shore.

Sometimes, fishermen were hired to secure a supply of liquor for an unknown party. Connections were made at the local speakeasy where the fishermen and “contact men” representing the unknown party would gather. The contact men gave the fishermen one half of a $100 bill. (Valued at more than $1,000 today.) The tear and the serial numbers on that bill had to match the other half, which was in the hands of the captain anchored at Rum Row. If the numbers didn’t match, the booze wouldn’t leave the ship.

In addition to the Coast Guard, rumrunners also had to be on the lookout for federal and local enforcement agents. Each afternoon, they all gathered at the local speakeasy to socialize and drink. When night crept in, they disbanded. The rumrunners went off in search of booze, and the enforcement agents went off in search of the rumrunners. Sometimes they would arrest their drinking buddies. Other times a bribe would persuade them to turn the other cheek.

A leaflet from 1920 denouncing the illicit smuggling of spirits.

A leaflet from 1920 denouncing the illicit smuggling of spirits.

“Otto St. George was a restaurant in Freeport and a speakeasy. Captains, mates and everyone else would meet there to get their schooner information. They would be told the schooner would be out at Jones Inlet, southeast, so many degrees, ride out an hour, etc., and you’ll find them. This is how they got their booze,” recounts
Scopinich.

Rumrunning was a lucrative business, even by today’s standards. Everybody wanted a piece of the action, and the mafia was no exception. Soon, the rumrunners had more to worry about than just the feds or Coast Guard. It was often cheaper and more expeditious for the mob to intercept the cash from a rumrunner in route to make a purchase than it was for them to buy and sell booze themselves.

“Prohibition was one of the best things that could have happened for organized crime,” says Claire White, Educational Programs Manager at The Mob Museum, naturally, in Las Vegas. “Hijacking and piracy were an expected part of the liquor trade along Rum Row as well as in rumrunning generally.”

Bill McCoy (pictured aiming a Colt-Browning machine gun) protected the Arethusa with an array of weaponry sold surplus after the Armistice of 1918.

Bill McCoy (pictured aiming a Colt-Browning machine gun) protected the Arethusa with an array of weaponry sold surplus after the Armistice of 1918.

Many gangsters, also known as “go-through guys” because they were willing to go through anyone and anything, were armed with “Tommy Guns” (the 32-inch stubby Thompson machine gun favored by Al Capone). The fishermen were no match for them and had no desire to lose their lives or partake in the violence. In fact, most rumrunners traveled unarmed for fear of getting caught by the Coast Guard while running a load. (If arms were discovered on board, the penalties were more severe. They’d rather risk their cargo and boat being confiscated than spending years in a federal penitentiary.)

Since they were unarmed, however, they were an easy mark for the “go-through guys” who usually attacked at dusk by racing alongside the boat, threatening the captain with a machine gun and forcing them to kill the engines. The captain was coerced to hand over the money roll, which could be quite substantial. Sometimes, the crew fought back. Many men died during these futile attempts, and the mortality rate on Rum Row grew.

A crowd gathers to watch men pouring confiscated rum overboard—the boat’s name is certainly serendipitous.

A crowd gathers to watch men pouring confiscated rum overboard—the boat’s name is certainly serendipitous.

Prohibition lasted for nearly 13 years until 1932, when president-elect Franklin Roosevelt, swayed by popular public opinion, cut the budget of the Prohibition Bureau. In 1933, the 21st amendment was ratified by the states, bringing an end to Prohibition. Most rum-running activities ceased completely. Alcohol was now so freely imported that prices plummeted. The rum-running boats became less economical to operate as gas and yard fees rose. Only the immense profits made during Prohibition’s heyday could support those increases.

Rum Row endured until the bitter end, even after the law had been repealed. A few ships stayed on to become floating factories manufacturing cheap liquor in less-than-sanitary conditions. The mob discovered greater earnings ashore, deriving profit from prostitution, drugs and racketeering. The Coast Guard evolved into the search-and-recover division of the federal government we know today, and the fishermen simply went back to fishing. As more members of this generation pass away and their stories fade with each passing tide, the legend of rum running—and the spirit of adventure it inspired—lives on.

In New York City, the M.M. Gardner was caught with cases of bootleg liquor and a large amount of gold.

In New York City, the M.M. Gardner was caught with cases of bootleg liquor and a large amount of gold.

This article originally appeared in the January 2022 issue of Power & Motoryacht magazine.

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