It was July 30, 1942, and the passenger ship SS Robert E. Lee had made its way from Trinidad to New Orleans with 235 souls aboard. The United States had entered WWII just eight months before following the attack on Pearl Harbor on December 7, 1941.  The ship had threaded the U-boat-infested waters of the Caribbean and was just 25 miles from the mouth of the Mississippi when she was struck by a torpedo fired by the U-166. Most passengers made it to the lifeboats, but 25 were killed in the attack.

Between 1942 and 1943, 20 U-boats would sink some 56 ships and damage another 18 in the Gulf of Mexico, and those German submarines would invariably pass through the Florida Straits, a passing between Cuba and the Florida Keys. While the U.S. Coast Guard and Navy maintained constant air and sea patrols out of Key West, the U-Boats still managed to slip through. Cuba had done its part as well, declaring war on Germany, as the U.S. had done, in December 1941. It then invited the United States to build air bases in the country and offered close cooperation with the U.S. military. It was welcome help too: the U.S. was woefully unprepared to fight a world war in 1941 and was lacking in ships, planes, and men.

Enter Ernest Hemingway, the future Nobel- and Pulitzer Prize-winning author. In 1942, Hemingway resided in Havana and may have been the most famous living author in the United States and Europe. His books were viewed as the literary expression of the quintessential American Spirit: restless, adventurous, and a bit rough around the edges. Hemingway had been rejected by the U.S. Army in WWI at the age of 17 because of poor eyesight. He instead joined the Red Cross (as Walt Disney had done) and was sent to Italy as an ambulance driver.  There on the front lines, he was badly wounded by shrapnel in both legs and despite his wounds continued to bring wounded Italian soldiers to safety. He was awarded the Italian Silver Medal for Bravery, the country’s third-highest award. Hemingway spent six months recuperating in a Red Cross hospital in Milan. During the interwar years, Hemingway wrote some great novels and short stories traveled extensively in Europe and Africa where he hunted big game.  During the Spanish Civil War, he witnessed a proxy war between fascist Germany, which was supplying the Franco regime, and the Soviet Union which was supplying the Republican forces.

Ernest Hemingway aboard the Pilar. (Photographer unknown/John F. Kennedy Presidential Library and Museum, Boston)

In 1934 Hemingway had commissioned the building of a fishing boat by Wheeler Shipbuilding in Brooklyn, New York. Named the “Pilar” she was mahogany built and 38ft long. She was powered by a 75hp Chrysler marine engine with a smaller Lycoming 4 cylinder turning a second propeller as a trolling motor. Her tops speed was about 16 knots. Heminway fitted her out as a deep-sea fishing boat with extra fuel tanks and a live well for bait. He also added a flybridge and outriggers. She also had a cut-down transom with a spanning roller for bringing in big fish. It’s not too much to say that the Pilar the first custom deep-sea fishing boat in the United States.

Hemingway and his crew went on to virtually create deep sea fishing as a sport in this country. He was the first to ever land a large blue-fin tuna without it being ravaged by sharks and caught some absolute monster black marlins in the waters between Key West and Bimini island in the Bahamas. We are talking about 1,000-pound fish here, and not just one. He was known to return to the dock with three and sometimes four huge fish aboard.

When WWII broke out, it was rather slow coming to the Caribbean and its shipping lanes. Germany’s U-boat fleet was a rather recent invention and early in the war, only about 20 U-boats were at sea at one time, mostly prowling off the coast of Great Britain. By 1942 however, the Kriegsmarine under Admiral Donitz was able to put 70 U-boats out to sea at a time and they began to range widely over the Atlantic and into the Caribbean and Gulf of Mexico.

Hemingway had moved from Key West to a farmhouse on a hill overlooking Havana in 1939, and by 1942 Cuba had become the most important U.S. ally among countries in the Caribbean. Hemingway’s first attempt to contribute to the war was to form a small counter-espionage unit of other writers he had worked with during the Spanish Civil war to try and keep tabs on thousands of pro-Franco Spaniards living in Cuba who, it was surmised, would also be Nazi sympathizers. Calling themselves the “Crook Factory” and operating out of Hemingway’s home in the hills, they spent the next eight months surveilling subjects and filing reports with the U.S. Ambassador in Havana, Spruille Braden. In a weird twist, reflecting the paranoia of the early days of WWII, it was later discovered that Hemingway himself was being monitored and watched by the FBI via Legal Attaché Raymond Leddy who was reporting to J. Edgar Hoover at FBI headquarters in Washington DC.