As the crisp, clear morning dawned on the first day of June 1943, offering a hard blue sky and perfect weather for flying, the spy sat in the passenger terminal of Portela Airport outside Lisbon waiting to make a phone call. The call would be a death warrant.

His vantage point was a wooden bench shoved up against a rear wall, and his eyes surveyed the hectic scene playing out in front of him with a professional watcher’s focus. It was just after six A.M., but the terminal was already crowded, a tempest of voices sweeping through the high-ceilinged room. It was a clamor fueled by desperation. Jammed into the boxlike space were men, women, and families determined to get a ticket on the 7:30 A.M. British Overseas Airways Corporation (BOAC) plane to Whitchurch Airport, England—a seat on the lifeboat that would be their escape from a Europe that was a rapidly sinking ship.

Get the Hell Out of Deutschland

Over the past three cataclysmic years, Nazi Germany had tightened its sharp coils around much of the Continent, but a resolute Portugal had nevertheless managed to carry on as a neutral state. And as tens of thousands of refugees—Jews, artists, Communists, and other freethinking enemies of the Reich—gathered up whatever they could and hurried to flee from the advancing goose-stepping hordes, they poured into Portugal. It was an oasis—yet one that was both temporary and ominously precarious. The country’s welcome, for one thing, was not open-armed: refugees with the proper visas were granted a mere 30-day residency. And while this statute was enforced by the Public Security Police more often than not with only a philosophical wink and a nod, the prospect of the country’s continued neutrality created more genuine terrors.

Neutrality was a dangerous national strategy. It was a contract not even worth the paper that had not been signed—at any moment the winds of war might come blowing in over the Pyrenees from Falangist Spain or Vichy France, and the refugees would be trapped at the end of the Continent, backed up against the roiling Atlantic as the Gestapo sighted them in the crosshairs.

The twin-propeller DC-3 that made four commercial flights each week from Lisbon to Whitchurch Airport, outside Bristol, offered a way out, the opportunity to escape once and for all from the Nazis’ murderous grasp. England would be a secure refuge; and from there, one could scramble to find a way to a new life in America, or Palestine. Dreams were fueled by such possibilities.

The plane to Whitchurch was an escape from a Europe that was a rapidly sinking ship.

The obstacles to obtaining a ticket on a BOAC flight out of Lisbon, however, were formidable. One hurdle—albeit one that might be jumped by a nimble scheme or a king’s ransom—was the requirement of a transit visa. The other was more inflexible, determined by the laws of an inexorable mathematics: there were only 13 passenger seats on a DC-3. The terminal was very much a seller’s marketplace. Day after frantic day, the bidding continued, fast and furious. Yet, like any fieldman on a mission, the spy would have found the discipline to pay only fleeting attention to the countless small and large dramas that fed the tumult storming about the terminal. He’d have concentrated on the faces. And, always conscientious, his glance would also have kept returning to the tarmac.

From his observation post on the bench, the view was perfect. Directly across the terminal, a row of three symmetrical windows, each as wide as a doorway and nearly as tall, gave an open view of the blacktopped runway. And there, with the early-morning sun simmering down on it as if a spotlight, the camouflage-painted plane—its name, Ibis, a tribute to the spindly ancient bird, painted in a cursive script under the cockpit window—the distinctive red, white, and blue BOAC stripes on its tail, stood, ready for boarding.

Slow and Steady

The spy waited, and he watched. He had been at the airport for days, ever since the order had been passed on from Berlin, and today was just like yesterday, and that had been the same as the day before. Yet his patience was undoubtedly fortified by the tenets any veteran professional would have learned the hard way: surveillance is a game played long; and, more often than not, its diligence is without reward—the quarry never shows.

Worse, this assignment, he knew, was more improbable than most, its logic more a prayer than a certainty. Simply because the Distinguished Personage had returned to England the previous January from Bermuda on a commercial Boeing flying boat—the first transatlantic air trip in history by a world leader—that was no guarantee he’d repeat the experience. After all, even the Distinguished Personage, in soul-searching retrospect, had conceded that his last-minute decision to forgo the waiting battleship with its muscular escort of fast destroyers was “a rash thing.” To think that he’d once again take the identical foolhardy risk, traveling on an unprotected BOAC flight in wartime, was like believing that lightning would indeed strike twice. Yet Berlin had its agents lurking about the souks and cafés in North Africa, and they were reporting a tantalizing rumor: at the conclusion of the military meetings in Algiers and Tunis, the Distinguished Personage would fly out of Gibraltar to Lisbon. From there, he’d catch one of the scheduled DC-3s home. It was only a question of what day, what flight.

This assignment was more improbable than most, its logic more a prayer than a certainty.

So, the spy dutifully maintained his vigil. He kept the image of the Distinguished Personage focused in his mind’s eye, but he never expected to see it in the flesh. It was 7:25 and the propellers on the Ibis had started to twirl, quickly picking up speed. Soon the plane would be taxiing to the runway and on its way back to England. He’d have passed another uneventful watch.

Then a pair of events occurred, one more improbable than the other. First, two people exited the plane. Walking down the flight of steps that had been quickly wheeled up to the craft’s passenger door were a young boy and an older woman. She, too, had the demeanor of a professional watcher, but her attention was more maternal than conspiratorial; the boy’s mother, or perhaps his nanny, it clearly seemed. But why were they coming off the aircraft? No one gives up a seat on the plane to England. Unless—

And no sooner had a startling hypothesis begun taking shape than it was confirmed. Climbing up the stairs was the stooped and portly figure of a man dressed in a voluminous pin-striped suit, a bow tie perched under the double chin, a seven-inch cigar wedged in the fleshy mouth, and a dark homburg resting on his head like a tea cozy. The outfit was as distinctive as any uniform. And for further confirmation, although none was really needed, there was the presence of the man trailing closely behind—tall, rail thin, and deferential, fitting to a tee the description in all the intelligence reports of the Distinguished Personage’s ever present personal bodyguard.

Now it was immediately apparent why the boy and his keeper had left the plane. They had been bounced, their tickets revoked—to make room at the last minute for the two late-arriving V.I.P.’s. In the electric moments that followed—and who could have blamed the spy if he felt as if war drums were pounding through his entire being?—he hurried to the nearest telephone to share his hard-won discovery: Winston Churchill, accompanied by the Scotland Yard inspector who habitually rode in his wake, would be on board the morning flight to England.

Winging It

Perched high on a hill in a stodgy, leafy neighborhood in the far reaches of Lisbon, the German Embassy rose up behind a tall wrought-iron fence like an impenetrable redbrick fortress. And on its very top floor, in a warren of dormer rooms that looked out toward the Atlantic and the unconquered world beyond the horizon, the Abwehr, the German military-intelligence organization, had set up its headquarters. Albert von Karsthoff was the station chief, although few inside the embassy gates, and even fewer outside, knew it.

A major in the German Army from a family of distinguished soldiers, he had, following the rules of his covert trade, re-invented himself with an assumed name (making sure, however, that his alias boasted a “von,” same as the surname that had been his genuine aristocratic birthright). And, more pretense, he was listed on the embassy rolls under the deliberately vague diplomatic title of “adjunct.” Even better, he lived his cover, as the professionals say with praise; and like the best disguises, it was rooted in his nature, only then some. Karsthoff tooled around Lisbon in a shiny Cadillac, often with his pet monkey sharing the front seat and a vial of cocaine stashed in his diplomat’s well-cut dark suit. Every evening was a fiesta. He cut such a flamboyant, fun-loving figure that it never occurred to the legions of Allied intelligence agents meeching through the shadows of neutral Lisbon that he was a fellow operative, let alone the Nazis’ master spy in the city. It was Karsthoff’s private line—five digits seared into every local Abwehr agent’s memory—that the spy called from the airport.

As luck would have it, Karsthoff was at his desk—either just arrived or, no less likely, still in his evening clothes preparing to head home after a long night—when the early-morning call came in. He listened with attention; the details of the Ibis’s flight plan were essential. At once he knew he had to make a decision, one that could affect his career—and, more consequentially, the entire course of the war. He had only moments to make it.

Climbing into the plane was a man dressed in a voluminous pin-striped suit, a seven-inch cigar wedged in the fleshy mouth.

The Wehrmacht, with typically tedious Germanic exactitude, was the country’s armed forces fortified by an allegiance to rules and procedures. The method for contacting the Luftwaffe’s air units in the North Atlantic had been set down in martial stone in “Luftwaffe Regulation 16, The Conduct of the Aerial War,” a work signed by no less an imperious authoritarian than Reichsmarschall Hermann Göring. The links in the chain of command, the manual decreed, must be rattled in a strict progression: first, contact the air-fleet commander in Paris; if he concurred that something crucial hung in the balance, he’d pass the particulars along to the Flying Corps Regional Command, based at the seaport town of Lorient, France; and from there an action order would at last be conveyed to the field commander at the Mérignac air base, near Bordeaux, whose squadrons hunted in the skies above the pounding waves breaking across the Bay of Biscay. But with the tick of every second counting, as well as with a battlefield wisdom born out of sour experiences that had taught that intelligence was of value only if it were translated into timely action, Karsthoff made a decision. He defied the regulations. In an act that would become part of the legend surrounding the entire operation, he made flash priority contact directly with the flying leader of fighter wing KG 40 at Mérignac.

German Junkers Ju-88 bombers in flight.

It was nearly 10 a.m. at the Luftwaffe base when the klaxon finally roared, tearing the quiet morning apart. At once pilots and crew scrambled across the tarmac to their fighters. Eight Junkers Ju-88s, fast, well-armed attack planes, took off angled toward the sun. Their powerful Jumo engines rumbling, the fighters climbed above the clouds. They raced west in a tight V formation, the pilots in the glass-roofed cockpits scanning the horizon for their prey.

Two Ju-88s vs. a DC-3

The pilot of the Ibis heard before he saw. Above him was the unmistakable sound of an aircraft. No, not one: two. Two planes hidden somewhere high in the clouds over his glass canopy, yet the whirl of their propellers and thrust of their engines and his sudden uneasy state would’ve made it seem as if they were close enough for someone to reach down and grab him by the scruff of his neck.

“I am being followed by strange aircraft,” the Ibis’s pilot radioed. As he spoke, two Ju-88s came crashing through the clouds, homing in on their target. “Indians at eleven o’clock,” the Luftwaffe flight leader announced. The Ibis’s only hope was to out-race the attack planes. “Putting on best speed,” the pilot, full of pluck, informed Portela air-traffic control. The lumbering DC-3 had no chance. The diving Ju-88s, with their supercharged engines at full throttle, emerged from the clouds at a dizzying speed, their guns trained like magnets on the slow plane. “A! A!” the Luftwaffe flight leader ordered. Attack! Attack!

At once a barrage of 20-millimeter cannon shells boomed across the sky and machine guns poured out bullets in a terrifying cascade of 1,200 rounds per minute. “Cannon shells and tracers going through the fuselage,” the Ibis radioed. “Wave hopping and doing my best.” Flames streamed wildly from the DC-3. Then the port engine gave out, and the plane fell from the sky.

Three parachutists jumped from the plunging plane, but flames engulfed their chutes, and they fell into the sea as if weighed down by boulders. The plane hit the water, too. It seemed for a moment that it might float, but then it sunk quickly into the dark, frigid waters of the Bay of Biscay. The eight Ju-88s flew around the crash site in slow, careful circles, their crews keeping a close watch on the ominously still sea. When they were convinced there were no survivors, the fighters returned to the base, their mission accomplished.

It seemed for a moment that the plane might float, but then it sunk into dark waters.

Only it was the wrong mission. It did not matter that the operation was a tactical success—it was a complete and utter strategic mistake. The crucial error lay in the intelligence that had provoked the aerial attack.

There had indeed been two last-minute arrivals boarding the flight to Whitchurch. And, true, one was a rotund and rumpled man in a dark suit, a long cigar wedged between his ample lips, and a homburg planted on his head, while the other, trailing behind, was long, lean, and sprightly. The problem was they were not the prime minister of England and his Scotland Yard bodyguard. They were two doppelgängers. Leslie Howard, the 50-year-old British actor who had won movie fame as the resourceful and indestructible Scarlet Pimpernel, had now been cast by the impulsive Abwehr agent as Detective Walter Thompson. The actor’s business manager and traveling companion, Alfred Chenhalls—who, down to the telltale cigar, was dressed for the part—had been given the role of Winston Churchill.

By the time the enraged British papers reported the downing of the defenseless civilian Flight 777, the genuine prime minister’s plane had safely landed in England. He had prudently taken off under the protective cover of darkness from Gibraltar in a military aircraft and had flown across the ocean surrounded by an attentive guard of R.A.F. fighters.

In the rush of wartime days that followed, each measured out in countless unnecessary deaths and woeful tragedies, the Abwehr’s misguided attempt to change the course of the war with one opportunistic assassination was relegated to a small, sad footnote in the larger and still very much uncertain march of history. “The brutality of the Germans,” observed the intended victim with an understandable anger, “was only matched by the stupidity of their agents.” But even Churchill in the end took refuge in a weary, if not mystical, stoicism, consigning the needless murders of the 15 people unlucky enough to have been on board Flight 777 to “the inscrutable workings of fate.”

Yet, fate would work its inscrutable way again to give the German High Command another opportunity—and this time a well-planned mission would be launched to assassinate the entire Allied leadership—F.D.R., Churchill, and Stalin—in a single daring commando operation.