Trolling for Nazis with Hemingway

By Patrick Hemingway Adams 

Editor’s note: this is a long-form piece originally printed in Field Ethos Journal 2022 Volume 1. 

This true story is derived from the recollection of Patrick Hemingway, Ernest’s second son. 

In the early part of 1942, Patrick Hemingway was a precocious and worldly boy of 14 years. He would often climb the secret stairs in the closet of his bedroom to reach the second story roof of his family’s Key West home. There he would sit outside and savor the absence of light pollution that helped him to identify constellations hanging low in the night sky. The oppressive humidity hardly let up at night in the Florida Keys, but he loved the solitude of his ritual and the way that the ocean breeze felt in the dark. 

On one such night, the wind brought a different kind of heat. His peaceful vigil was shattered with flashing bright lights and distant flickering flames as torpedoed vessels burned and sank just beyond his perspective of the Southern horizon. Tendrils of black smoke wafting up from the wreckage became clearly perceptible in the moonlight. 

From the roof of the Hemingway home, young Patrick watched the savage aftermath of the earliest violent actions committed against the United States by Nazi Germany. These acts of war perpetrated by the German Navy began as part of Operation Drumbeat, or the strategic targeting of American military and supporting vessels along the North Atlantic coastline of the United States. Torpedo attacks by German submarines (Unterseeboot or U-Boat) met little resistance against unarmed and unsuspecting ships so close to the perceived safety of the American mainland. 

Following the devastating success of their North Atlantic and Eastern coastline offensive, German Naval Command would redirect their fleet to ambush ships traveling from ports along the Gulf of Mexico. This critical shipping route of war supplies and crude oil made for an irresistibly juicy target. Indeed, the German subs were torpedoing fish in a barrel. 

Between the months of January and August 1942, German U-boats sank over 600 Allied ships, causing the deaths of thousands. These losses would account for nearly one quarter of all ships sunk during the Second World War. German submarine commanders informally referred to the action as “American Shooting Season.” Something had to be done. 

Summer in Cuba  

A few months later, Patrick and his younger brother Gregory were sent to spend the summer at their father’s Cuban estate, Finca Vigia. They arrived to find an electric atmosphere as the region prepared for war. The situation in the Gulf and on the Atlantic Coast had deteriorated into total chaos. The locals along the coastal states and island chains increasingly felt that the American Government had been downplaying the devastation caused by German attacks. The propaganda obsessed newspapers’ refusal to accurately report on the extent of the damage and loss of lives sparked further outrage and indignation. 

This powder keg of distrust began to inspire large groups of boat owners, fishermen, and pleasure cruisers to take up arms themselves and join in on the pursuit of the menacing U-boats that stalked their coasts like underwater wolves. The locals were restless, frustrated, and now armed to the teeth. One such would-be privateer was Ernest Hemingway, American novelist and famed devotee of all things adventure. 

Hemingway possessed a famous penchant for intelligence gathering work and had used his notoriety and connections to great effect working with the fledgling intelligence organizations of the Spanish Republican Armed Forces during the Spanish Civil War. By the end of the conflict he had become deeply fascinated with the dark world of espionage, and he cultivated his reputation as a willing participant for the right cause. 

Hemingway had continued this tradition in recent years by aiding Havana-based American Naval Intelligence officers in the identification of Spanish fascists with Nazi sympathies as they began to appear in Cuba. Spruille Braden, American ambassador to Cuba, personally recruited Hemingway and his network of connections to help aid American interests in the region. Galvanized by the increasing threat of enemy attack in his own backyard, Hemingway hatched a plan to aggressively fight back. His brazen scheme would involve his fabled boat, an intrepid crew, and an even more audacious plan that would become the stuff of classic American legend. 

Profile of Ernest Hemingway aboard the Pilar. Photograph in the Ernest Hemingway Collection of the John F. Kennedy Presidential Library and Museum, Boston

The Boat 

Purchased in 1934 from Wheeler Shipyard, Inc. of Brooklyn, NY, Hemingway’s beloved fishing boat, Pilar, was named for his second wife’s nickname. She was a 38-foot fishing boat fitted with a custom “flying bridge” that allowed it to be steered from on high. She could be driven by a 4-cylinder trolling motor or a 75HP Chrysler “Crown Marine” L-Head 6-cylinder main engine.  She was capable of 16 knots and had a shallow draft of 3.5 feet. Unlike the standard Wheeler factory white paint scheme, her hull had been painted an impossibly dark black like the eyes of a shark. 

Hemingway’s connection to the American Embassy in Havana afforded him a special requisition for Pilar’s conversion to a fightin’ patrol boat, and so she was loaded to the gills with guns, rations, and radio equipment. 

Patrick fondly remembered that there were quite a lot of hand grenades onboard. The crew were outfitted with a diverse collection of personally owned hunting rifles, sporting shotguns, and American taxpayer funded .45-caliber submachine guns.  The firearms were stowed in oiled sheepskin cases to keep the caustic sea spray at bay.  

Hemingway, crestfallen, reluctantly determined that the boat’s gunwale was unable to support the heavy recoil of a crew served machine gun, but if there was a crown jewel of the Pilar’s arsenal, it was Papa’s homemade explosive charge. Crafted from an industrial fire extinguisher stuffed full of dynamite, this bomb was handy enough to be maneuvered into position by one strong man; it would constitute the coup de grâce of Hemingway’s offensive attack plan. Like the pirate ships and privateers of yore that sailed the same waters, Pilar was all wood, steel, and gunpowder. She was ready for war. 

The Crew 

Hemingway’s crew was composed of as motley a group of irregulars as had ever set out to sea. His sons, Patrick and Gregory, accompanied the expedition and were given the forwardmost bunks. They brought their books and their .22 rifles. 

Hemingway’s first mate, Gregario Fuentes, reprised his usual role on the boat. Born of the Canary Islands and an artful fisherman, Fuentes would later be presumed by some to be the inspiration for the old man in The Old Man and the Sea. 

A noncommissioned officer of the United States Navy was seconded to serve as a radio operator.  He had previously been stationed at a far east clandestine listening post tasked with collecting intelligence on the Chinese. He claimed to have been familiar with most high-ranking Communists around the world, as he had been listening to their voices for years.   

The rest of the crew was made up of three professional Jai Alai players hailing from the Spanish Basque country. Locally notorious for their intense athleticism and imposing physicality, these men would constitute the Pilar’s naval infantry and boarding party. One crewmember had been officially blackballed from playing the sport after killing a man in the Jai Alai court. (By way of explanation for this, he merely stated that he had been accused of losing control of his own strength.) 

The Plan 

The premise was simple: to observe and patrol for German U-boats and evidence of German troop activity near the isolated islands lining the deep-water channel between Cuba and the Bahamas. 

3D illustration of a German U-Boat patrolling the roughs seas of the North Atlantic

The execution would be very precise. It would not be a booze cruise searching for a needle in a haystack, but rather a carefully planned patrol designed to intentionally confront the enemy U-boats as the sloping grand banks forced the ships into a bottle neck trench.  As a dedicated fisherman, Hemingway was intimately familiar with the region’s oceanic features. His crew had fished around every reef, shoal, and sandbar in their area of operations. He knew where the submarines had to be.   

It was within this stretch of channel that Hemingway hoped to pose the Pilar as a “Q-Boat,” or decoy vessel, and lure the Germans to surface for one of their famous 88mm deck gun attacks.  When the unsuspecting submarine motored up close enough to Hemingway’s boat, the trap would be sprung. Counting on surprise and light fighting resistance aboard the U-boat conning tower, Hemingway planned to unleash a torrent of preemptive machine gun fire and grenades to clear the deck. The Pilar’s flying bridge was determined to be the perfect height from which to initiate the broadside attack in a faithful homage to classical nautical warfare. 

 Once the conning tower could be secured and the main hatch breached, the fire extinguisher bomb would be ignited and thrown into the belly of the sub. The Pilar’s crew would then retreat to a safe distance for celebratory drinks to wait for the boom. 

The plan was just crazy enough to work. 

The Hunt 

Hemingway’s hunt began with the establishment of an improvised beachhead on the small island of Cayo Confites.  Strategically located to monitor the mouth of the deep-water channel Northeast of Cuba, this little cay was home to postcard-esque beaches and sparse palm trees.  It was solely inhabited by a Cuban Army radio operator who maintained a relay station and comms tower. Hemingway’s team would use Cayo Confites as a resupply station and safe haven to stash his sons when imminent submarine contact was expected. 

And so the patrols began quietly.   

Ernest Hemingway captained the Pilar across the suspected U-boat routes while the crew caught fish. They ate endless amounts of fish and fruit. They passed around dog-eared novels and told stories. Patrick and Gregory took turns laying on the bow as it bucked in the waves to shoot at flying fish with their .22 rifles. Patrick recalled that Gregario always had dark Cuban chocolate to give the boys. 

On most days the boys were sequestered back on Cayo Confites. The seriousness of the mission was not lost on Hemingway; he wished to keep the boys a part of the adventure, but as safe as possible from the most dangerous threats. Hemingway’s crew returned to the cay every evening to relay observation reports back to the American Embassy and check after his temporarily marooned sons. 

Gregory “Gigi” Hemingway and Patrick “Mouse” Hemingway with Boise (cat), as a kitten, at Finca Vigia – Photograph in the Ernest Hemingway Collection of the John F. Kennedy Presidential Library and Museum, Boston

The young boys didn’t always mind being left behind. They spent the days fishing and sailing a small skiff around the island. The nearby bay teemed with aquatic life, and they were never short on grouper or snapper for supper. On one particular afternoon of unsupervised bliss, a violent squall surprised the boys outside the cove and capsized their skiff. Patrick remembered this time as the most wonderful summer he would ever have. 

Sometimes the boys’ cautionary restrictions were lifted in order to employ Patrick as a teenage tunnel rat. Many of the surrounding islands had cave networks that required investigation for evidence of German caches. Patrick was of suitable size and maturity to take point on these spelunking excursions; he explored dozens of tropical caverns with his flashlight in search of Nazi loot. It was a fitting job for a boy nicknamed “Mouse.” 

Late in the summer, wealthy British socialite Winston Guest arrived to briefly assist in the hunt. Much more than just a hunting buddy of Hemingway’s, Guest was second cousin to Winston Churchill and famously studly with a rifle. Eager to get in the fight, he brought along a Westley Richards .577 Nitro Express double rifle and a fat live pig. Ernest and his boys liked to joke that Guest, “… smelled good like a millionaire should,” in friendly parody of a popular Winston cigarette advertisement. The pig was stationed on Cayo Confites and eventually avoided the machete by swimming to the Cuban mainland.  

On several occasions, U-boats were spotted in the distance and even within naked eyesight of the lighthouse on the Bahamian side of the channel. Hemingway expressed frustration that the running speed of the Pilar was inadequate to close the distance that was sometimes only as far as 1,000 yards. Despite a dogged effort, their Nazi prey remained elusive.   

Patrick’s summer of Nazi hunting came to a close when it was time for highschool to start. He was soon shipped off to Catholic boarding school in New England. Patrick struggled with the frustration of connecting with other boys at school, having been sworn to secrecy regarding his very real and very confidential wartime activities–tough secrets for a 14-year-old boy to keep. But keep them he did. Besides, the other lads probably couldn’t have understood what it had been like to pursue dangerous enemy submarines across the deep sea.  

In the end, Hemingway and his crew never had the opportunity to test their plan, not for lack of trying, but rather because the stars did not align for a confrontation. The tactical relevance of his gathered intel is still unknown. But his experience as a submarine hunter would later inspire the action-filled third act of the novel Islands in the Stream.   

Later Papa Hemingway would again bring the fight to the Germans by participating in the Allied invasion of Europe when he landed at Normandy Beach as an embedded journalist. He was present at the Liberation of Paris and subsequently accused of leading a small militia force in violation of the Geneva Convention. In 1947, Ernest Hemingway was awarded the Bronze Star for Bravery in recognition of his wartime reporting. 

We may never know if German sailors slept fitfully in their bunks, terrified at the idea of being keel hauled by bearded American civilians that haunted the tropics with fishing boats, makeshift bombs, and beverages. But it is clear that Hemingway’s mission of high adventure took more than just courage and determination–it flat out required brass cajones to even attempt to go toe to toe with the Nazi’s combat-hardened submarines on their terms.   

At the very least, his attempt to single handedly destroy the German U-boat fleet should serve as a lasting reminder that real bravery can inspire others to be bold, too. The bold and the brave don’t care if a plan sounds crazy.  Like Ol’ Papa Hemingway, we should never stop looking to the horizon for fortune, glory, and as much adventure as we can find.  




From the FE Films Archive


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