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What Tyler Kent did for love of one country rocked another.

At 11:15 Monday morning, May 20, 1940, on Gloucester Place near the heart of London, a police driver parked a crowded sedan. Out stepped a man from Special Branch and two from Scotland Yard, as did Captain Maxwell Knight of British spy agency MI5 and U.S. Embassy Second Secretary Franklin Gowen. A knock at No. 47, a townhouse broken into furnished rooms, summoned a maid. When one of the men from the Yard asked for Tyler Kent, the maid went to fetch the landlady, and the raiding party pushed inside. One officer trailed the servant; the others rushed to the second floor of the house, where they flashed credentials and a search warrant at the proprietress. Again an official asked for Kent. The landlady pointed to an apartment. A policeman tried the handle, then knocked on the door to the flat. “Don’t come in!” a voice said. “Don’t come in!”

The raiders crashed in to find their man barefoot beside a rumpled bed, wearing only striped pajama bottoms. Kent and Secretary Gowen recognized one another from the embassy, where Kent, a suave 28-year-old with aristocratic good looks, worked as a clerk. Captain Knight announced that a search would occur, warning the young American that anything he said might be used against him. An officer moved toward to the apartment’s other room.

“You can’t go in there!” Kent shrieked. “There is a lady.”

So there was, wearing the top to the striped pajamas. Knight asked Kent if he possessed any U.S. government documents, particularly pertaining to the embassy.

“I have nothing belonging to the American government,” the younger man said. “I don’t know what you mean.”

Knight knew better, and while his subordinates watched Kent and his mistress—a married Russian woman named Irene Danishewsky—dress themselves, he and Gowen searched the flat. In suitcases and boxes were thousands of copies of embassy papers, as well as photographic plates and files marked “Chamberlain,” “Churchill,” “Jews,” and so on. In a cupboard they found a book bound in red leather, embossed in gold, and secured by a brass lock. Sensing it might have significance, Knight himself jimmied the hasp to reveal pages of fine penmanship in blue ink naming hundreds of Britons, some quite famous. One of the latest entries to the roster was Tyler Kent’s name. On Kent’s writing desk was a letter to him from a notoriously right-wing Scottish politician. In a blink of deduction, the man from MI5 realized that he had struck gold.

Knight told Mrs. Danishewsky—whose phone he had tapped and whose innocence, at least in the matters at hand, he accepted—that she could go. His subordinates manhandled Kent and their discoveries to the curb, where an officer hailed a cab for Gowen and Knight. The vehicles sped the mile or so to the U.S. Embassy, where the raiders stowed Kent in room 119 and hauled the cache to Ambassador Joseph P. Kennedy. Holding the red ledger, Knight suggested Kennedy examine the rest of the swag.

The impromptu visit did not startle Kennedy: before the raid, Knight had asked him to suspend Kent’s diplomatic immunity and Kennedy, hearing the context, had complied. But the paperwork was a shock. As Kennedy studied it, he realized that not only had Kent compromised State Department codes worldwide, he had copied Kennedy’s own often-Anglophobic and occasionally pro-German personal memoranda.

Worse, the impertinent underling had copied many secret telegrams between President Franklin D. Roosevelt and Winston Churchill. The covert communiqués had started in September 1939, as Churchill assumed the position of First Lord of the Admiralty for the second time, and continued through winter and into spring, when Churchill became prime minister. In their exchanges, Churchill and Roosevelt, assuming they were writing in confidence, mulled how FDR might slip Britain war materiel in bald violation of U.S. law. Word of this in the press would strangle Kennedy’s public career, never mind the impact on November’s presidential election.

Kennedy and Knight huddled. Knight had thought the clerk was up to no good, but all the spymaster had expected to find at his flat was evidence MI5 could use against another of Kent’s Russian women, whom Knight suspected of Nazi leanings. The red book delivered that evidence and much more, which would delight Churchill. Knight laid out possibilities. Kennedy officially dismissed Kent, clearing Scotland Yard to arrest the embassy factotum, and he vanished into the arms of British jurisprudence.

The raid had far graver repercussions than its mishmash of bedroom farce and spy thriller suggested. The findings convinced British authorities that a Nazi fifth column had infested London and that the U.S. Foreign Service was riddled with treachery. Kent’s stash of documents gave Churchill the evidence he needed to change British law so he could lock up domestic opponents, meanwhile tugging his embattled island and its American cousins closer. The revelations also shoved the Roosevelt administration into action. Code experts scrapped or rewrote existing American ciphers as the government weighed the threat Kent and his archive posed at home, where a battle was raging between interventionists and their isolationist foes in Congress. That was the fight Tyler Kent, who hated the New Deal and felt its furtive foreign policy agreements excluded him and his countrymen, was planning to fuel with his incriminating secret telegrams.

In 1940 Americans were wary of global conflict. Isolationists took comfort in the Neutrality Act, passed five years before and amended three times since to keep FDR from joining foreign frays or even aiding combatants. Charles Lindbergh was crusading for rapprochement with Hitler, and he was not alone. Pacifists and isolationists in the Senate and the State Department suspected Ivy Leaguers in the diplomatic corps of dragging the United States into war. Tyler Kent knew those suspicions to be true, and with the copies of telegrams showing Roosevelt violating the Neutrality Act, at least in spirit and probably in deed, he had the papers to prove it. He meant to show his purloined documents to well-placed isolationists, including family friends high in the State Department.

Kent’s motives were rooted deep in his family history—the source of his connections at State, where he enjoyed the patronage of old timers with political ties to his father, a Republican Party organizer Theodore Roosevelt had rewarded for getting out the vote in Virginia by naming him a consul. Tyler, born in China in 1912, spent his childhood caroming from one consulate to the next, rarely visiting the States and not experiencing American life until at 14 he enrolled at a boarding school in Connecticut and then Washington, D.C. A few years at Princeton propelled him to Paris, where he finished at the Sorbonne in 1934.

Kent had a Virginia gentleman’s manners, but that courtliness barely masked a vein of racist resentment. Though not exposed directly to Southern culture, he had grown up on tales of Confederate legacy; a great-grandfather, Judge John Hendren, had been Jefferson Davis’s secretary of the treasury. Part and parcel of the clan’s shabby-genteel background were ancient regional grudges toward northerners that young Kent absorbed.

Friendships never lasted for Kent, a brilliant loner with a gift for languages. He studied Latin for 16 years, was fluent in Italian, German, and French, and learned Russian in Paris in only six months. He also behaved as if he was the smartest fellow in any room at any time. “The trouble with Tyler is that he has such powers of concentration that he can read over a textbook and get the point the other boys have to dig for,”a schoolmate’s father said.

Returning to Washington, D.C., in 1932 seeking a Foreign Service job, Kent found the State Department was not hiring. But he knew the game. When the Roosevelt administration arrived, cronies of his father, including Secretary of State Cordell Hull and Assistant Secretary Walton Moore, got him hired as a clerk, assigned to Moscow under William C. Bullitt, the first U.S. Ambassador to the Soviet Union.

Kent made the most of his lowly perch in the Soviet capital. Convinced wealth and fame were his due, he quickly figured out how to acquire the former. When not working as a receptionist and translator, he partnered with a fellow clerk to work the black market, buying jewelry and furs sent by diplomatic pouch to be sold in New York. Kent’s share of the profiteering bought a car and paid the rent on a dacha where he often spent weekends with a soignée girlfriend, Tanya. When it came to the recognition he craved, Kent was less successful. In spite of or perhaps because of his brilliance, he rubbed colleagues the wrong way. “I recall him as a sort of an oddball around the embassy, very much a loner, an unpleasant personality, full of himself, and giving the impression of pursuing aims of his own,” said George Kennan, then a young Foreign Service officer assigned to the embassy.

Moscow was the perfect incubator for Kent’s subversive instincts, yen for the spotlight, and prejudices. In the shadow of the Kremlin, his reservoir of bias acquired a corrosive new tint. “The Jews are basically responsible for the establishment of Soviet Russia,” he explained in a 1982 BBC interview. Bolsheviks were evil; Bolsheviks were Jews; Jews were evil. Trips to Europe, where Hitler was on the rise, convinced him Germany should invade Russia and eradicate the Reds. Kent generally shirked his clerking duties and often did his translating at his apartment. At the embassy, he had access to a file room strewn with communiqués that he began to read, perusing diplomatic reports about trouble in Europe and other top-secret material. It infuriated him that Foreign Service officers in Europe were lobbying for the United States to go to war. He scorned Kennan and other Foreign Service officers he saw as sons of the liberal Yankee establishment. He was sure he knew better than they—but nobody cared what he knew or thought, which Kent also resented. When Hitler invaded Poland and England declared war on Germany, he concluded someone had to keep the U.S. out of the hostilities “because of the disastrous effect it might have on America,” he later told the BBC. He started sneaking documents to his apartment, perhaps sharing them with Tanya.

On August 23, 1939, Germany and Russia signed a nonaggression pact. En route to that sudden shift, the Soviet Union had become less kindly disposed toward Americans—at a bad time for Kent. Driving in Moscow, he struck a pedestrian in a crosswalk, breaking the man’s leg. Kent was about to go to trial when word came that Joseph Kennedy, U.S. Ambassador to England, needed a cipher clerk. Eager to avoid irking the Russians, the embassy whisked Kent— who had no experience with codes—to London.

Kent reached England in October, landing himself on MI5’s watch list en route because he sailed aboard the same ship as a Gestapo operative under surveillance by the spy agency. It did not help that the American newcomer later dined with the German.

Despite Kent’s lack of training, he grasped code work quickly. The embassy used two ciphers: Code Grey was confidential, Code Brown strictly confidential, and each used letter and number groups. Kent was one of four code clerks working mostly days and occasional night shifts. Early in 1940 he moved onto Gloucester Place, where he had a bedroom and a sitting room, no kitchen. In bespoke suits and shirts, polished hair parted not quite down the middle, Kent could pass for a well-fed young British banker.

Off hours he roamed London, building a new social life. He frequented an expatriate hangout, the Russian Tea Rooms— a louche setting where White Russian émigrés hobnobbed with titled Britishers. Owner and former Czarist admiral Nikolai Wolkoff sold the best caviar in town. His daughter, Baroness Anna Wolkoff, was the doyenne of the scene, which tended to right-wing extremism and hatred of Jews. Another Tea Rooms fixture was Archibald “Jock” Ramsay, a Scottish member of parliament from Peebles and founder of a secret society, the Right Club, dedicated to anti-Semitism and resisting Churchill’s calls for total war against Germany. These were Tyler Kent’s kind of people.

Soon Ramsay invited Kent to join his club, offering the vague title of steward, and introduced the American to Baroness Wolkoff, the group’s secretary. Eventually Kent would accept Ramsay’s precious red leather Right Club ledger for safekeeping.

Kent sometimes worked into the wee hours, alone at the embassy, handling the world’s most sensitive papers, copying those he wanted and packing facsimiles in his briefcase. At home he filled suitcases with filched secrets, including a telegram sent January 29 at 7 p.m. to Roosevelt from Churchill using the dual pseudonyms Naval Person and Johnson: “PERSONAL AND SECRET FOR THE PRESIDENT FROM NAVAL PERSON QUOTE I GAVE ORDERS LAST NIGHT THAT NO AMERICAN SHIP SHOULD IN ANY CIRCUMSTANCES BE DIVERTED INTO THE COMBAT ZONE ROUND THE BRITISH ISLANDS DECLARED BY YOU (STOP) I TRUST THIS WILL BE SATISFACTORY. ENDQUOTE JOHNSON”

Kent was juggling several women, including an intense but chaste liaison with the baroness and a decidedly less platonic affair with Mrs. Irene Danishewsky, whom he had met at a Russian New Year’s ball and who would hurry from the flat she shared with her husband on Edgeware Road for morning romps on Gloucester Place. Sometimes she and Kent spent afternoons shopping on Jermyn Street. Evenings—when he was not at home pondering how to use his files to keep Churchill and Roosevelt from betraying Americans into war—Kent frequented the Tea Rooms. Amid the bigoted bray, he resumed his boastful ways and began to crow to the baroness about his pilfered papers, unaware that in wartime capitals the walls have ears.

The Tea Rooms and the Right Club were in MI5’s pocket, penetrated by a squad of thrill-seeking society beauties Maxwell Knight had recruited as operatives. Agent “Miss Amor” had joined the Right Club months before. Dining on February 24, 1940, with Baroness Wolkoff, Amor learned that her dinner companion was “spending a great deal of time with this man from the American Embassy and concentrating on him.” Knight connected the dots backward to Kent palling around with the German spy. By April Fools Day, Amor had discovered that Ramsay and Wolkoff deemed Kent an “increasingly important contact.”Wolkoff told Amor that Kent was providing Ramsay and herself with “incriminating papers.” On April 12, 1940, another of Knight’s glamorous snoops reported that Kent had given Wolkoff “confidential information” based on a conversation between Ambassador Kennedy and Foreign Secretary Halifax, who favored talks with Germany. Knight himself found that Ramsay was dashing to Gloucester Place in a “small racing car,” as the maid said later, to join Wolkoff in browsing samples from Kent’s archive. The Churchill-Roosevelt telegrams particularly interested the pair, and they borrowed several to photograph.

Churchill became prime minister on May 10, 1940. In his zeal to destroy Germany he wanted to identify and imprison anyone—especially native fascists and sympathizers—who might give aid and comfort to the enemy. Home Secretary John Anderson was resisting his leader’s demands for a clampdown, explaining that Churchill had not proven a link between the British right and the Third Reich.

Knight was sure Kent could lead authorities to a fifth column. If he could arrest the American in possession of secret documents and tie him to British traitors, then Churchill could persuade Anderson and Parliament to let him seize every suspicious alien and appeaser in Britain. There was no time to lose. Allied forces in France were falling back before the Blitzkrieg. Hitler was closing on the Channel coast. Fears of a German invasion ruled Britannia.

Everything happened in a flash. On May 20 Knight arrested Kent and, with the Right Club ledger, secured the ammunition Churchill sought. The copied telegrams were icing on the rancid cake. Kennedy disavowed his code clerk. Two days later Parliament rubber-stamped a law authorizing internment of anyone suspected of associating with the enemy. Kent disappeared into custody. No word reached the press.

Across the Atlantic, the Democrats nominated FDR a third time, and his campaign unfurled without a whisper that the president had trampled the Neutrality Act. The British, doing their part, delayed Kent’s trial until the eve of the election. Beforehand, they haggled to use the notorious telegrams as evidence against Kent, persuading the State Department to release two. At a preliminary hearing Kent’s lawyers asked whether Ambassador Kennedy, when asked by Knight to lift Kent’s diplomatic immunity so Knight could raid the clerk’s apartment, had possessed the authority to do so, and if so, had the ambassador followed protocol? By trial’s start, however, the only pertinent witness on those points, the former ambassador himself, was aboard a Pan American World Airways Clipper out of Lisbon, winging toward America.

The case of Rex v. Tyler Gatewood Kent opened at the Old Bailey on October 23, 1940, a month into the Blitz. The press was banned; brown paper covered the courtroom windows. A military observer who attended the secret trial recalled,“The fact that every now and again the sirens sounded, and one and all—Judge, Learned Counsel, prisoners, witnesses—repaired to underground cellars to await the All Clear, only added to the drama.”

The jury convicted Kent “of five offenses of obtaining and communicating documents which might be of use to the enemy for a purpose prejudicial to the safety and interests of the state,” in the words of Justice Richard Tucker, who sentenced the accused to seven years of penal servitude. Baroness Wolkoff, tried separately, got 10 years. Interned without trial, Archibald Ramsey spent four years in London’s Brixton Prison before angry MPs on both sides of the aisle, who had obtained copies of the telegrams used in the trial, forced the Home Office to release the unrepentant Scotsman.

British authorities locked Kent up on the Isle of Wight, but Americans only learned of his imprisonment when the 1944 parliamentary debate erupted about Ramsay’s internment. The story made front pages in the U.S., triggering a three-day discussion of the case by isolationists on the Senate floor. Some Americans saw Kent as a martyr whose only sin had been to act boldly in an effort to keep their country out of a European war. Others thought an American court should have tried him. News coverage elicited from Kennedy a belated but typically pithy comment.“If we had been at war I wouldn’t have favored turning Kent over to Scotland Yard or have sanctioned his imprisonment in England,” the former ambassador said in a September 1944 interview. “I would have recommended that he be brought back to the United States and shot.”

Even if Kent’s guilt seems evident the question of who he worked for remains open. British historian Nigel West thinks Kent probably did spy for the Soviets, who in 1940 were Germany’s allies. Long after Kent left Russia it came to light that the glamorous Tanya, of the dacha weekends, was an NKVD agent. In the 1950s former German spy Otto Jahnke claimed that during the war he ran Kent as an agent. No conclusive proof supports these assertions, however.

In the end, Tyler Kent was political poison on either Atlantic shore, a man of flagrantly flawed character who believed he had a right to disclose secret documents.

After the war Churchill conceded there had been no fifth column after all. Britain freed Kent and deported him. When he returned home aboard the RMS Silver Oak, his mother and a phalanx of reporters were waiting at the pier in Hoboken. “I’m very glad to be back in the United States,” Kent said at an impromptu news conference. “I think in the near future I will have something to say of interest to the people of this country.” Then he quickly went into seclusion, there to remain. Knowing further publicity would bring animosity and challenges to his patriotism, he evaded pacifist and isolationist admirers who hailed him as a hero. He had found the fame he craved, or at least its poor relation, notoriety. Now all he needed was wealth. Within six months of his return, Kent married a rich divorcée of a certain age with a farm in Maryland where, at last, the wayward son of the South embraced the squire’s life.


Originally published in the October 2013 issue of World War II. To subscribe, click here.