The Tale of Tyler Kent: Spy or a Snowden?

The Northern Ireland link of a spy who enraged President Roosevelt and  delayed Mussoloni's entry into World War Two | Belfast News Letter

I have recently been on a real espionage kick, and one of the controversial cases surrounding World War II was that of a cipher clerk at the American Embassy in London, Tyler Kent (1911-1988). There are many reasons not to like Kent as a person, reasons that I will make abundantly clear, but the question here is given his activities, was he a spy or a whistleblower?

Kent was born to a prestigious family, his father was the consul to Manchuria at the time of his birth and a major supporter of President Theodore Roosevelt. He proved highly intelligent, attending Princeton University, the Sorbonne, the University of Madrid, and George Washington University and speaking seven languages (Simkin, Kent). By the time he graduated, the job market wasn’t terribly open for diplomats, but Kent managed to use family connections to get a position at the American Embassy in the USSR in 1934, with Secretary of State Cordell Hull pressuring Ambassador William C. Bullitt to take him in. Bullitt assigned him as a lowly clerk but he was eventually promoted to cipher. There, Kent was known as a rather unlikable loner who made no bones about acting like the smartest person in the room. As George Kennan, at the time a coworker, recounted about him, “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 his own” (Rand). He fell in love with a woman who worked for the NKVD, which led to suspicion that he was giving intelligence to the USSR. In 1939, he injured a pedestrian in a car accident, and was promptly transferred to Britain, where he would work for Ambassador Joseph P. Kennedy.

From almost the very start, Kent was under suspicion by MI5. He was seen in the company of Ludwig Matthias, a Swedish businessman of German origin who was suspected of being a Gestapo agent. While working at the embassy, Kent was noticing a lot of secret correspondence between President Roosevelt and First Lord of the Admiralty Winston Churchill, correspondence not even known to Prime Minister Neville Chamberlain. Socially, he frequented Russian tea rooms in London, which were full of Russian emigres who had fled the Bolshevik Revolution. There he found kindred spirits, people who were staunchly anti-Communist and anti-Semitic. Among these people he met Anna Wolkoff, the daughter of former Tsarist Admiral Nikolai Wolkoff, who brought Kent into The Right Club. The Right Club was a group of pro-Fascists headed by Scottish Conservative MP Archibald Ramsay, who wanted the war between Britain and Germany to end. Ramsay stated in his autobiography, “The main object of the Right Club was to oppose and expose the activities of Organized Jewry, in the light of the evidence which came into my possession in 1938. Our first objective was to clear the Conservative Party of Jewish influence, and the character of our membership and meetings were strictly in keeping with this objective” (Simkin, The Right Club). At The Right Club, Kent expressed anti-Communist, pro-Fascist, and anti-Semitic sentiments. He, like his boss Joseph P. Kennedy, believed that Britain was going to lose the war and that the United States should stay out of the conflict. Both Germany and Russia didn’t want the United States in World War II at the time given the Molotov-Ribbentrop agreement, so Kent being against American involvement served both of their interests at the time. He proceeded to steal and make copies of over 1500 documents, including secret correspondence between Roosevelt and Churchill. He did so by pocketing copied documents scheduled to be burned and Ambassador Kennedy had, according to Kent, commissioned the copying of political documents for his private collection, providing the perfect cover for him to copy said documents for his own use. Had this correspondence been publicly released, Roosevelt’s secret violations of the Neutrality Acts would have become known to the American public; polling at the time indicated that most didn’t want to get involved in World War II. Roosevelt had publicly pledged for the election to keep the United States out of the war, so the exposure of these documents could have lost him reelection. Kent showed these documents to Archibald Ramsay and Anna Wolkoff, intending to transmit them to U.S. Senate opponents of FDR’s foreign policies. Ramsay did not make a copy of the Churchill letters but planned to eventually introduce these to the House of Commons in a parliamentary effort to oust Churchill. On April 13, 1940, Wolkoff made copies, which Kent presumed was for Ramsay, but took them to Italian Assistant Naval Attache Don Francisco Maringliano, Duke of Del Monte, who transmitted the documents to Berlin, ending up in the hands of Wilhelm Canaris, the intelligence chief of the German Army. However, MI5 had multiple agents embedded in the Right Club, including Joan Miller, who reported on these activities.

Maxwell Knight of MI5 reported the events to Ambassador Joseph P. Kennedy, who realized that the documents stolen contained secret correspondence, compromised American diplomatic codes globally, and also contained evidence of his pro-German and anti-British views on the conflict (Rand). Kennedy promptly waived Kent’s diplomatic immunity, which allowed him to be arrested by MI5 and prosecuted by the British for violating the Official Secrets Act rather than be taken to the United States for trial. This was a way to prevent Kent from being able to testify in the United States, for otherwise the trial would be public per the Sixth Amendment and Kent would speak of Roosevelt violating the Neutrality Acts. There was no press surrounding the matter at the time and he was convicted of violating the Official Secrets Act in a secret trial and was imprisoned until the end of the war. Anna Wolkoff was also tried and convicted, with Archibald Ramsay being interned. His trial and conviction would not be publicly known until 1944. As I have written previously, there were great efforts by the British and Germans to influence American opinion in the two years preceding the attack on Pearl Harbor, and Kent’s efforts certainly could have been another. It is not conclusive whether Kent was in fact a spy. Professor Igor Lukes (2021) concludes that he was a spy for the Soviets while in Moscow and London, providing documents on the behest of his girlfriend and later Ludwig Matthias. Historian Nigel West found it probable that Kent spied for the Soviets and the FBI suspected as much. However, other sources have held that Kent spied for the Germans with a former Gestapo officer claiming that he was on his payroll and that Matthias was either a Gestapo agent or a suspected Gestapo agent.

Kent After World War II

Kent’s postwar activities do not engender sympathy, to say the least. After marrying a wealthy heiress, suited for the lifestyle had become accustomed to, he stayed out of the limelight for some time and became the publisher of a segregationist newspaper in Florida with ties to the KKK. The FBI remained suspicious of him, investigating him six times between 1952 and 1963. Kent joined Liberty Lobby Board of Policy in the 1950s, an organization founded by Willis Carto that portrayed itself as a patriotic conservative group but as I have written before, it was a front for something much more sinister. Through his newspaper, perhaps in a way of paying back his former boss Joseph P. Kennedy, he accused President Kennedy of being a communist. After his assassination, Kent publicized the conspiracy theory that Kennedy was assassinated by the Soviets because he was turning away from communism.

Kent stayed associated with Carto as it became increasingly known that Liberty Lobby was a front for Carto’s pro-Nazi bigotry. In 1982, Kent was tracked down for an interview by Robert Harris of the BBC, and when asked if being called anti-Jewish was a fair description of him, he admitted, “Yes, that’s a fair description. Because the Jews are basically responsible for the establishment of Soviet Russia”. That year, he attended a conference of Holocaust deniers in Chicago and claimed the Holocaust to be a Jewish hoax (Beschloss, 190).  By the 1980s, Kent had blown through his wife’s money through libel suits and failed financial schemes, spending his last years living in poverty in a Texas trailer park.

Kent was undoubtedly a whistleblower who may have changed the course of history had his information reached the American public in 1940. He may have also been a spy for the Soviets or the Nazis, a great irony for a man who would portray himself as a patriot, and was certainly a man who held repulsive views.


Beschloss, M. (2007). Presidential courage: brave leaders and how they changed America. Simon & Schuster: New York, NY.

Lukes, I. (2021, May 11). Truth as an Instrument of Evil: What Could Soviet Spy Tyler Kent Cause? Forum24.

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Rand, P. (2013, October). The Secret Sharer. World War II.

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Robert Harris Report on Tyler Kent. BBC.

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Simkin, J. (2020). The Right Club. Spartacus Educational.

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Simkin, J. (2020). Tyler Kent. Spartacus Educational.

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