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.

A few weeks after Hemingway had formed the Crook Factory, he approached Ambassador Braden with another idea: He wanted to use the Pilar to hunt for U-boats. Reports of German subs in the straits between Cuba and Florida were rampant among easily spooked ship captains and fishing boat skippers. Adding to these claims were suspicions that German subs were using the numerous bays and inlets of the Cuban coast to cache supplies and food. There had even been reports of U-boats surfacing near commercial fishing boats and taking part of their catch in order to feed their crews. in February 1942, U-boats surfaced off the island of Aruba to shell the largest refinery in the Caribbean with their deck guns and sink tankers in the area with torpedos.  Submarine attacks on shipping in the Caribbean Sea in 1942 would sink 260 ships, more than the number of ships sunk in North Atlantic convoys.

The oiler SS Pennsylvania Sun torpedoed by the German submarine U-571 on 15 July 1942, west of Key West, Florida. The Pennsylvania Sun survived the attack and returned to service in 1943. A critical shortage of tankers in WWII would be the bane of U.S. naval operations planners.

Hemingway made a simple if outlandish proposal to the ambassador. The Pilar would pose as research or simple fishing vessel in the hopes that a U-boat might surface near her to either seize her or investigate what she was doing so far out to sea. Then he’d lure the sub close and with his crew of just five men, engage the Germans with concealed machine guns, grenades, and satchel charges, sink the sub, and either kill or capture the crew. He also believed he might be able to seize code-breaking logbooks and communications equipment from the sub before she might sink. Hemingway seemed to be taking his inspiration from the famous Q-ships of WWI. These ships appeared to be small “Tramp Steamers” too slow to keep up with a convoy but had drop-away bulkheads that concealed naval cannons and machine guns. In WWI, submarines mostly operated under the “Cruiser Rules” which required them to attack civilian vessels on the surface with their deck guns after affording the merchant crew the chance to man their lifeboats. Initially, Q-Ships were pretty successful in taking advantage of surfaced subs, which were following these rules. They sank several German submarines until one managed to escape and report that the British were using armed warships disguised as merchant ships. This contributed greatly to Germany abandoning the Cruiser Rules and going over to unrestricted submarine warfare whereby U-boats would attack submerged and without warning.

Ambassador Spuille agreed and Hemingway found himself the only private U.S. citizen in Cuba to command his own Privateer, a civilian vessel outfitted for war. That the ambassador would approve a scheme like this gives one some idea of how desperate the U.S. was in the first year of the war. The government was willing to entertain just about any idea as long as it offered some hope of aggressive action against the enemy. Hemingway called the affair “Operation Friendless” after one of his cats.

Ambassador Spuille approved Hemingway for tightly rationed fuel supplies and an HF/DF or ‘Huff-Duff” radio direction finder to track U-boat transmissions and armaments. It was found that the Pilar was too flimsy to mount a .50 cal machinegun on her deck, so Hemingway was given some Thompson submachine guns, rifles, grenades, and even several bazookas. Using his own resources, Hemingway fashioned something he called a coffin bomb that he intended to log from his own flying bridge onto the conning tower of a submarine and down its hatch to blow it up. The ambassador assigned a hard-drinking Marine sergeant, Don Saxon, as his radio operator. Sgt. Saxon would be the only member of the crew on active duty.

The Pilar put to sea initially on short cruises during the day and returned each night filing reports on ship movements and other observations. In doing this Heminway critically reduced his chances of finding a U-boat which, as a matter of doctrine, would submerge during the day and run on the surface only under the cover of darkness. He explored the cays and bays of the coast searching fruitlessly for signs of German supplies stashed away for U-boats by Nazi sympathizers. In December the Pilar observed a freighter from neutral Spain being trailed, or perhaps even towing, what Hemingway believed might be a submarine. His small boat was unable to close with the freighter to identify it. When the ship reached Havana and the crew and passengers were questioned, nobody knew anything about a submarine.

After the war, critics accused Hemingway of being unserious about what he was actually doing when it was revealed that his two young sons were accompanying him on these patrols. That claim has some merit, but it may have also just been explained by Hemingway’s failings as a father. There are numerous points in his life when he lacked judgment. For example, as a journalist during the Spanish Civil War, Hemingway was said to have taken up arms and joined in the fighting himself on occasion, a major breach of journalistic ethics.

For some 18 months, Hemingway and his crew plied the waters around Cuba without any sign of a U-boat. Listening to radio chatter was found to be useless as Sgt. Saxon did not speak German and Hemingway never made any documented attempt to obtain a German-speaking crewman. But the crew did obtain copious amounts of alcohol. Sgt. Saxon was said to consume about 20 drinks per day, mostly gin. Hemingway had written to his wife about the wartime hardships of having to go without wine or gin for days at a time, and having to resort to rum and grapefruit juice as substitutes. Attempts at rationing himself and his crew to just a couple of drinks a day almost provoked a mutiny with members of the crew threatening to seize the vessel from Ernest and make for the nearest port with a bar. However, these threats were never acted upon.

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In a 1988 book, The Faces of Hemingway by Denis Brian, Winston Guest (a longtime friend of Hemingway’s), and a member of the crew described the action. The Pilar had been at sea all morning in bad weather and they had tucked in behind a Key to eat a lunch of tuna sandwiches and beer. A lookout was posted to continue to search the horizon and he called out about midway through the meal:

“‘Unidentified ship about two miles to the north-west!’

Throwing sandwiches to the wind the crew ran on deck, with Hemingway grabbing the binoculars off the guy who’d spotted the ship.

‘Where? Can’t see a damned thing.’

Guest pointed.

‘A bit further to the north, Ernie, low and black in the water, look.’

‘Got it, what do you make of it, Winston?’

‘It’s a sub okay, can’t make out from here if it’s a Jerry, or one of ours.’

Hemingway was in no doubt.

‘It’s a Jerry, a 740 class, cruising slowly. Get the anchor up and let’s get after the bastard.’

As Guest describes it they pulled out from behind the Key and started what would appear to be a fishing pattern (one of the crew members already had a barracuda hooked so they looked authentic), pulling slowly closer and closer toward the unsuspecting U-Boat. Their plan was to get as close to the U-Boat as possible and then blast it with everything they had. But suddenly they were spotted and the captain — obviously taking no chances — ordered the submarine to dive. Hemingway, disappointed, ordered the Pilar back to Havana at speed. Once there he made a report of the sighting, which was given a DF classification, which, according to Guest, meant ‘not credible.

But a few days later a message came through for Hemingway saying that his report was 100 percent right. It had indeed been a submarine that had been spotted by several tankers on the course given by Hemingway. Apparently, the sub had, after being spotted by Hemingway, landed four men at the mouth of the Mississippi, where, after a bit of a fight, it was captured by an alarmed Coast Guard vessel, and taken in tow to New Orleans.”

(I have been unable to find any record of a U-boat captured by the Coast Guard off Mississippi and taken into New Orleans. Hemingway calling it a “740 class” may refer to the German Type VII submarine which was about 770 tons in displacement.)

There are some who dispute whether the Pilar ever spotted a submarine, but Hemingway’s son Gregory was also there and added that they cursed and yelled at the submarine from a distance of about 1,000 yards as it outpaced them. After the U-boat had made its escape, Ernest asked his son to make him a gin and tonic.

In July 1943 the U-boat campaign in the Gulf of Mexico was coming to an end and a coded message on the radio ordered the Pilar back to port. The Pilar was a bit of a mess at that point, needing extensive repairs to engines and propeller shafts as a result of the long hours she had spent at sea. Some claimed that it was all a lark for Hemingway, including Mario Ramirez Delgado, a Cuban naval officer who had actually sunk a German submarine. Delgado quipped that Hemingway’s excursions as a sub hunter were just, “a playboy who hunted submarines off the Cuban coast as a whim.”

Playboy or not, that was not the end of the war for Hemingway. He packed off to Europe for the Normandy landings as a correspondent for Collier’s Magazine. Hemingway seemed not only drawn to the war’s dangers but, as in the Spanish Civil War, unable to resist being an active combatant. While embedded with the 22nd Regiment of the 4th Infantry Division in its drive on Paris, Hemingway again was able to insert himself into the fight. On August 3, 1944, he entered the village of Villedieu-les-Pôeles, and speaking French acted as an interpreter for the Army. The mayor informed them that a group of SS-men was holed up in the basement of a home nearby. Being taken to the house he armed himself with grenades and shouted down into the basement in both French and German for the soldiers to surrender themselves. Hearing no reply, he then chucked three live grenades down into the basement. Hemingway did not stick around to see the aftermath but later told others that he had killed plenty of Nazis while covering the war.

Ernest Hemingway

Two days later Hemingway and famed photographer Robert Capa were riding on a captured German motorcycle driven by an Army private when they drove headlong into a German anti-tank gun position that opened up on them with machine guns. They abandoned the bike and hid in the woods for several hours until the Germans gave up looking for them. In that scrape, Hemingway would suffer what must have been his sixth serious concussion. Shortly after, Hemingway joined the 5th Division near Rambouillet. While there he fell in with a group of French resistance fighters. It wasn’t long before he caught the attention of the OSS which was in charge of intelligence in the region. An OSS colonel named David Bruce gave Hemingway a letter in his own handwriting that authorized the correspondent to carry weapons and take part in military activities, something the Geneva Convention very specifically forbade. Hemingway was said to have removed the correspondent’s badge from his uniform and was left only with the 4th ID shoulder patch. He then set about leading this small band of French resistance fighters on reconnaissance missions ahead of the division. They called him “captain’ and apparently followed his orders without question.

His activities were enough for other correspondents to complain to Patton at 3rd Army HQ in Nancy. Hemingway was summoned there on October 4 to answer charges that he had been an active participant in combat action. In his own defense, Hemingway produced letters from Army officers who praised his language assistance with the French and denied he took part in the fighting.  Hemingway did not offer the letter from the OSS colonel, however. Collier’s decision to no longer pay him for his services would mean Hemingway would remain in Europe for 10 months at his own expense, but he filed 10 stories for publication with Collier’s regardless. Being cleared of the charges and rejoining the 4th Division, Hemingway covered the disastrous battle in the Hurtgen Forest in November 1944. There the 22nd Infantry Regiment would be badly mauled, losing over 2,000 men in just 18 days. Hemingway again took part in the fighting, this time out of sheer desperation. A German platoon assaulted the regimental command post and the author, armed with a Thompson sub-machine gun, helped fight them off.

Hemingway contracted a very bad case of pneumonia during this campaign but was there in December to see the 5th ID advance across a three-mile front in the last battle he would witness. He returned to the U.S. in March of 1945 two months before the German surrender.

In June of 1947, a small ceremony was held at the U.S. Embassy in Cuba, Hemingway was presented with a Bronze Star for his service as a war correspondent. The citation read that Hemingway moved, “freely under fire in combat areas in order to obtain an accurate picture of conditions. Through his talent of expression, Mr. Hemingway enabled readers to obtain a vivid picture of the difficulties and triumphs of the front-line soldier and his organization in combat.”

Given that he only filed 10 stories in as many months in Europe, it’s entirely possible this Bronze Star had more to do with what he did for the OSS, leading French resistance fighters while a civilian, than with his activities as a writer. This is supported by the fact that Ernie Pyle was by far a more famous War Correspondent whose work was carried in more than 300 U.S. newspapers. Pyle was killed in Okinawa and posthumously awarded a Purple Heart, yet his only other award from the government was the Presidential Medal of Merit given for outstanding contributions to the war effort.

Ernest Hemingway

Hemingway would go on to receive the 1952 Pulitzer prize and the 1954 Nobel Prize for literature for his book The Old Man And The Sea which was a tale about an old fisherman trying to land a giant marlin. In 1961, suffering from depression and a host of other physical ailments including hypertension, Hemingway took his own life with a shotgun. He was 62 years old.

After his death, some 332 unpublished works of his were discovered including a novel called Islands in the Stream about an artist living in the Bahamas who ends up in Cuba hunting down the crew of a sunken Nazi submarine. The book spent 24 weeks on the NY Times Best Seller list. It was adapted into a 1971 movie starring George C. Scott, who bore a passing resemblance to Hemingway. The boat in the movie was modeled after the Pilar.

As for the “Privateer” Pilar, she outlasted Nazi U-boats, Hemingway, and even the ravages of time. She now sits restored and on blocks at Hemingway’s residence outside Havana in the care and custody of the communist Cuban government.

This article was originally published in March, 2021.