Archive: ‘My two years with the bootleggers’ – Cayman Compass

In this July 1973 column, published in The Norwester, Bodden Towns Justice of the Peace William J. Wood relates some of his memories from the Prohibition Era, when Americas Great Experiment in banning the manufacture or sale of liquor put a special value on liquor that could be imported despite the Customs mens close watch. Wood was among the Caymanians who sailed aboard boats which took part in the lucrative trade of getting foreign liquors to US buyers on the high seas.

In the 1920s, Prohibition was in full swing in the United States and the country was dry. All the distilleries were closed and the importation of liquor was banned. Millions of dollars were spent guarding the Canadian and Mexican borders and the long sea coastlines. Of course, this was almost impossible, as there were no planes in those days to patrol the boundaries of sea or land.

And so arose the profession of bootlegging, or rum-running as it was called, in order to make a quick dollar. What actually happened on the land borders is unknown to this writer, so my story is based on the sea boundaries.

Captain Ben Granger, from Texas, was the first to come here and spread the news. He bought an island-built schooner by the name of Island Home and shipped a full crew of Caymanian seamen. He also installed in his vessel an engine which was essential in this kind of work. Large cargo ships brought loads of the finest liquors from the Continent and placed them in bonded warehouses in Havana. Captain Ben, in the initial stages, loaded his boat in Havana and then came to Cayman and had the liquor taken ashore and removed from the cases into sacks, which would stow better and be less conspicuous when landed in the US. This was done on several trips and helped the island greatly as our economy was very low during that period. Shortly afterwards, this practice was discontinued and all boats in that trade loaded at Havana and went to their pre-arranged sites off the American coast.

It was a common sight to see eight or nine boats anchored in Havana harbour awaiting their turn to load. These boats were manned by seamen from the Cayman Islands and British and Spanish Honduras. It was at that time that I joined the gang at Havana. We would leave by sail or motor vessels for the Isle of Pines, take a ferry to Batabano and a train from there to Havana.

When $1,000 bills were used, I worked as a seaman on several boats during over two years there the schooner Cayman, the yacht Narkeeto, and the auxilliary boat Carson, just to name a few. We were well paid and well treated. In fact, there was the first and last time that I ever saw $1,000 bills. We would load at Havana with the best whiskies, gin, cordials and Champagne and would go to a pre-arranged rendezvous off the American coast. This was necessary so that our associates from the American side would know where to locate us.

When their boats came in sight, they would have to give us the correct signals, otherwise we would not allow them to come alongside. We always kept outside the 12-mile limit, so that Coast Guard boats would not interfere with us. Some boats had a purser aboard and sold direct to the smaller boats, while others were unloaded by their owners.

All boats had to be armed with high-powered .303 rifles, in case hijackers wanted to come aboard and help themselves. This happened on several occasions although the crew were armed, because the hijackers came as friends and bought some liquor, and then with pistols caught the crew off guard and compelled them to load their boats, besides carrying off any money or valuables they could find.

One schooner named the Emerald left Havana and has never been heard of since. It is believed that hijackers took the cargo, killed the crew and sank the boat. All boats would have several blank manifests; if some of the liquor was sold, a new manifest would be made showing a different amount and kind, in case they were boarded by the Coast Guard.

It was all very nicely planned and many millions of gallons of good liquor got into the United States. Only the rich could buy this kind of liquor, as it was priced at $35 to $40 a bottle on shore. It was all very thrilling and lucrative, but dangerous, as well. Besides hijackers, when bad weather came, we had to take up anchor and get underway. With our contraband cargo we could not go into port, but had to stay out there and take it.

I remember one time when a heavy northwest storm came up. We had to leave our anchorage and go out to sea for many days and nights, battling the high seas and winds, before we could return. With the exception of Captain Ben Granger and Thomas Jackson, both now deceased, no one seemed to save their money. They spent it all in Havana on women, wine and a jolly good time.

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Archive: 'My two years with the bootleggers' - Cayman Compass