During the summer of 1961, Lee Harvey Oswald, a 20-year-old American living in Minsk, wrote a letter to his mother in rural northern Texas. Marguerite Oswald, who raised Lee as a single mother, had worried endlessly about her younger son after he got a discharge from the Marines and ran off to the Soviet Union. 

In the letter, Lee dropped word that he had married a Russian girl named Marina. He also asked for a copy of George Orwell’s novel 1984, a request that belies Oswald’s reputation as a fanatic. Oswald, it seems, wanted to read Orwell, a banned anti-communist author, hardly the impulse of a Marxist-Leninist ideologue. 

“Dear Lee,” Marguerite responded on July 8, 1961. “Received your letter yesterday. I’m sending a package today, please let me know if you receive it.” She included deodorant, shaving cream, dish towels, a potholder, and a can opener. 

“I couldn’t imagine where I could get the novel 1984,” she added, “but the wife [of a visiting couple] has read it (she lives in New Jersey) and she promised to get a copy for me. It will probably be a month or two.”

After living under real socialism, Oswald was disillusioned. In a public meeting, his new wife was charged with being an “enemy of the people” for marrying an American. He was eager to return to the United States. Whether Marguerite ever sent Orwell’s book to her son is unknown. But two and half years later, a paperback copy of 1984 was found by police searching Oswald’s home after his arrest for killing President Kennedy. 

If Oswald read 1984 — and he was known to be a serious reader — he knew the fictional world of Winston Smith, the frustrated functionary in a not-very-futuristic Ministry of Truth, who seethes about the government lies that he propagates. Smothered by the mantra “Big Brother is Watching You,” Smith knows the Thought Police are on to him. They monitor his ideas, his movements, his heretical thoughts. Eventually they charge him with being an Enemy of the People.

Orwell’s fiction was Oswald’s reality. The ex-Marine didn’t know it, but the CIA was monitoring his every move — as was the KGB. A multilingual operations officer named Reuben Efron in Washington was reading his correspondence and Efron reported to counterintelligence chief James Angleton, one of the preeminent intelligence officials in the Western World.

The CIA did not disclose Efron’s role in the surveillance of Kennedy’s killer for 62 years, until the spring of 2023. It was, evidently, an important secret to keep.

Sixty-two years later, the question of “Who Killed J.F.K.?” still resonates weirdly yet profoundly in American politics. Within days of taking office, President Trump issued Executive Order 14176, mandating the “full and complete” release of all records related to the assassinations of J.F.K., Robert F. Kennedy, and Martin Luther King, Jr. When the fully declassified J.F.K. files were posted on the National Archives website on March 18, the New York Times hastily proclaimed the mostly unread records confirmed that “Oswald did it.” The editors of the Washington Post said none of the newly released 77,000 pages — which they presumably had somehow read and examined in full the same day they were released — contradicted the official theory of a lone gunman. 

These speed-reading savants overlooked the CIA’s pre-assassination file on Lee Harvey Oswald. Not fully declassified until April of 2023, the Oswald file was compiled — and controlled — by James Angleton throughout J.F.K.’s presidency. The sheer weight of this file, along with the level at which it was produced, pulverizes the agency’s claims it had only “minimal” information about the accused assassin before J.F.K. was killed. It shows Kennedy’s putative killer was being monitored at the highest echelon of the clandestine service before J.F.K. travelled to Dallas. 

Marguerite Oswald would later boast to writer Jean Stafford that her son was “a very intelligent boy” — being a stamp collector; a chess player; and a reader of Darwin, Hemingway, and Norman Vincent Peale. Her pride was not misplaced. Lee was intelligent, self-taught, and headstrong. He dropped out of high school to join the Marines and graduated from basic training as a radar operator in June of 1957. He went on to a succession of far-flung posts culminating with a stint at the top-secret air base in Atsugi, Japan, where he earned a security clearance.

Taking a less than honorable discharge in September of 1959, Lee said he was going home to take care of his mother but stayed in New Orleans for only a few days before boarding a ship to England. He claimed in a passport application that he was going to attend a college in Switzerland. Instead, he made his way to Helsinki, Finland — though no one knows exactly how. 

Oswald’s intrepid journey bears the first traces of what Senator Richard Schweiker called “the fingerprints of intelligence.” The Warren Commission, relying on information from the CIA, said Oswald travelled from England to Helsinki by air on October 10, 1959. Yet, according to a Finnish security service file on Oswald, made public in 2024, there is no record of Oswald passing through any border-control entry point. 

So how did Oswald get to Finland? Oswald soon dropped a hint. The CIA’s pre-assassination Oswald file shows that in August of 1961, while living in Minsk, he wrote to the US Embassy in Moscow to say he could catch a “military hop” flight from Berlin back to the United States. A “military hop” might explain how Kennedy’s accused killer was enabled to reach Helsinki without encountering any border control.

In October of 1959, Marguerite Oswald was surprised to learn her son had turned up in Moscow saying he wanted to live under communism. When Lee didn’t respond to her letters, Marguerite wondered if her son had been enlisted as some kind of “secret agent,” a claim for which she would be forever mocked. 

“If my son was an agent of the United States,” she told Stafford, “this should be known.” 

With the supreme condescension of a New Yorker staff writer, Stafford didn’t deign to comment on the ludicrous suggestion that someone in the US government might have wasted a minute thinking about her pathetic son. 

In fact, CIA files released in recent years show that Marguerite Oswald was rather prescient while the sophisticated Stafford was ignorant. Lee Harvey Oswald, it is now well documented, was the subject of abiding interest to Angleton throughout Kennedy’s presidency. If there is no proof that Oswald was a secret agent of the CIA, he certainly was of secret and continuing interest to Angleton, whose thoughts and motives remain unknown.

Not only was Angleton reading Oswald’s mail, but the spy chief was also collecting reports on Oswald from the State Department, FBI, and Navy, as well as other CIA offices. By November of 1963, Angleton had compiled a 194-page dossier on the ex-Marine, a file that was not fully declassified until two years ago.

It would be difficult to conjure up two more different twentieth century Americans than Lee Harvey Oswald and Jim Angleton. 

Oswald grew up poor in New Orleans and the Bronx, which led him to read Karl Marx and sympathize with the downtrodden. Bullied for playing with black kids, he became outspoken in support of civil rights. As a Marine, he was regarded as a capable soldier with oddball left-wing views. He dropped out of the military and moved to the Soviet Union, an audacious act for a young man of modest means. 

Angleton grew up posh in Boise and Milan. He went to prep school in England and Boy Scout jamborees in Hungary. As a precocious literary entrepreneur at Yale, he befriended Ezra Pound, whose fascist sympathies he shared — at least for a while. In World War II his millionaire father’s connections smoothed his way into the Office of Strategic Services. Fluent in three languages, he in turn impressed the bosses of the OSS, British intelligence, and the newly created Central Intelligence Agency. 

Multiple identities propelled the upward arc of his career. In the OSS, Angleton was known as “ARTIFICE.” To Hitler and Mussolini’s translator Eugen Dollmann (whom Angleton saved from a war crimes tribunal) he was “Major O’Brien.” To a Jewish friend in Tel Aviv, he signed his letters “Alex.” In FBI files he was “Bureau Source 100.” In CIA cables he was “Hugh Ashmead.”

Angleton’s protean thinking created the CIA’s Counterintelligence Staff in 1954. His voracious vision of intelligence collection led him to take an interest in Oswald in 1959. For, despite their differences, Oswald was exactly the type of character that Angleton, with his powerful literary imagination, spent his life seeking out and investigating in his attempt to separate Cold War fact from fiction.

The circumstances that led to the end of Angelton’s career as the CIA’s chief counterintelligence officer led in turn to attempts to dismiss him as a paranoid madman. In fact, he was a careful, deliberate, and imaginative thinker, whose decisions and actions, taken mainly in private, would prove to be enormously consequential. During his extraordinary 27-year career, he obtained Nikita Khrushchev’s “secret speech,” searched for moles, identified Russian double agents, spied on Americans, and looked the other way as his friends in Israeli intelligence stole their way to a nuclear arsenal. His heavy drinking and fixed ideas eventually alienated even his admirers. He was fired in December of 1974 after the New York Times exposed his domestic spying operations.

Angleton has come to embody the American spy in fiction and cinema. He was the model for Harlot, the legendary spymaster whose ghost haunted Norman Mailer’s epic novel of the CIA. He was Ed Wilson, the corrupted title character of Robert De Niro’s 2006 movie, The Good Shepherd. Most recently, Angleton wandered through the Netflix series A Spy Among Friends, as a dupe of Soviet spy Kim Philby

James Jesus Angleton is our iconic spy, our cold warrior, our mole hunter, and now, we now know, our Oswald handler — at whatever degree of separation. 

On October 31, 1959, Soviet authorities admitted Oswald as a comrade from the American proletariat. He was given a factory job in Minsk and a spacious apartment in the heart of the Byelorussian capital.

On Monday, November 2, 1959, the Washington Post ran a brief item on Oswald’s defection. A week later, Angleton put Oswald’s name on a short list of about one hundred Americans whose overseas mail was specifically targeted to be intercepted, opened, read, and copied. The CIA’s surveillance of Oswald had begun. It would not cease until J.F.K. was dead. 

In Minsk, Oswald soon chafed at the communist regimentation. The factory job was dull, the mandatory meetings duller. Oswald clashed with coworkers, while plainclothes agents of the NKVD kept close watch on an arrival who turned out to be as much of an oddball in the Soviet context as he was in America. 

Still, Oswald made friends easily and his Russian slowly improved. With Ernest Titovets, a medical student who spoke decent English, he went to the opera and listened to Paul Robeson records. Lee courted one girl, Ella German, who dumped him, and won over a second, Marina Prusakova, who married him. 

“Lee wanted to become a political organizer,” Titovets told me in an interview. He says he is quite certain that his friend from long ago did not kill President Kennedy. 

A January 1958 memo, not declassified until last month, revealed that Angleton told the FBI that one purpose of his mail surveillance project (known by the code name HTLINGUAL) was to identify persons living behind the Iron Curtain with US ties who could be approached as “sources or contacts.” 

Twenty-two months later, in November of 1959, Angleton put Oswald under mail surveillance. Angleton’s comments about the recruiting purpose of mail surveillance — concealed by the US government for 67 years — constitute more intelligence-world fingerprints on Oswald. 

Another new record, unreported by either the Times or the Post, reveals that Angleton subsequently lied under oath, in 1978, about the mail surveillance of Oswald. That made him the third senior CIA officer known to have deceived investigators about his knowledge of the accused assassin while J.F.K. was alive. The others were deputy director Richard Helms and psychological warfare officer George Joannides.

One untrue CIA statement about Oswald might be attributed to incompetence. A second misleading statement could be a symptom of bureaucratic CYA (Cover Your Ass). But three false statements in an investigation of a presidential assassin cannot be considered a sign of incompetence. What we see in the new J.F.K. files is a pattern of malfeasance. 

Orwell’s novels were known to the young Russians with whom Oswald associated while living in Minsk, Ernest Titovets told me in an email. He had first learned about Animal Farm from a BBC production. Titovets is now in his eighties and still an active medical researcher in Belarus.

“I do not recollect Animal Farm or 1984 ever coming up in conversations with Lee,” he added. “Let me remind you that Lee, already at the tender age of fifteen years old, read Manifesto by Karl Marx with its ideas of dictatorship, of the proletariat, democracy, equality, etc. It was, most likely, what had fired him in the first place to become a Marxist and act accordingly. In view of that, his interest to 1984 was rather of peripheral importance as far as the makeup of his mind was concerned. Lee was only curious.”

And yet, how curious that Oswald was curious about 1984. Winston Smith’s greatest fear is that the Thought Police will detect his irrepressible rage at the surveillance society in which he lives. He dreads punishment for thoughtcrime, for questioning the benevolence of the regime.

Oswald, like Smith, was being watched — by both the Soviet and the American versions of Orwell’s Thought Police. After all, the subjects of Angleton’s mail surveillance included Martin Luther King, Jr., Vice President Hubert Humphrey, congresswoman Bella Abzug, economist Paul Baran, and vaccine pioneer Linus Pauling. They had nothing in common other than that Angleton, the formerly fascistic counterintelligence chief, wished to infiltrate their thoughts in service of US foreign policy.

On June 9, 1962, Reuben Efron, the deputy director of the HTLINGUAL operation, read in the Washington Post that Oswald and his wife had returned from the Soviet Union. He recalled Marguerite’s letter to her son in July of 1961, pulled a copy from the HTLINGUAL archive, and sent it to Angleton’s deputy.

“This item will be of interest in Mrs. Egerter and also the FBI,” he said.

Elizabeth Ann Egerter was the file supervisor in an office known as the Special Investigations Group, or CI/SIG. She had controlled access to Oswald’s dossier since November, 1959. She added Efron’s report to the growing Oswald file. 

By early 1963, multiple CIA operations were converging on Oswald.

In April 1963, an FBI informant obtained copies of Oswald’s letters requesting pamphlets from the Fair Play for Cuba Committee in New York, and soon became a spy for the CIA’s top secret AMSANTA program to penetrate Cuba’s leadership.

In August 1963, student agents in the AMSPELL program engaged in political and propagandistic action against Oswald when he went public by handing out FPCC pamphlets in New Orleans. 

In October 1963, a top-secret photo surveillance program in Mexico City (code name LIEMPTY) captured Oswald “coming and going” to the Soviet Embassy in pursuit of a visa. A top-secret wiretap (LIENVOY) overheard him talking to a suspected KGB agent. Subsequent CIA cables about Oswald were slugged LCIMPROVE, a code name for top-secret operations against the KGB.

The CIA’s surveillance of a future presidential assassin and the pattern of malfeasance around him doesn’t much interest the Washington press corps. Writing in SpyTalk, former Washington Post reporter Michael Isikoff dismissed the surveillance of Oswald by consulting Fred Litwin, the author of several self-published books. “Why are all these documents in the hands of the CIA before the assassination?” Litwin asked. “Well, if you go to the Soviet and Cuban embassies in Mexico City at the height of the Cold War, guess what? Your name is going in a CIA file. If you defect to the Soviet Union, yeah, you’re going to be in a CIA file. So, Oswald was always brushing up against American intelligence, but he wasn’t under constant surveillance.”

Maybe. But if all this long-running surveillance of Oswald was so innocent, why did top CIA officers hide it from investigators and consistently lie about it? To cover up their incompetence, sigh Langley’s beleaguered defenders. The CIA men dissembled, they dutifully explain, because they were innocent of wrongdoing. They just overlooked Oswald… Sorry about that, Mrs. Kennedy. 

On November 22, 1963, President John F. Kennedy was gunned down as his motorcade passed through downtown Dallas. The gunfire that left him dying in Jackie’s arms erupted in front of the Texas School Book Depository where Oswald worked. As policemen rushed into the building, they found Oswald drinking a soda pop in the second-floor cafeteria.

Oswald then went home and got his pistol, perhaps indicating he had knowledge of Kennedy’s assassination and felt that he needed to protect himself. He set out on foot for the nearby movie theater. Stopped by a policeman, he shot the officer — a response that suggests some measure of fear and guilt — and went into the theater, where he was arrested. 

That evening, in Miami, the CIA’s AMSPELL assets sprang into action. With the approval of psyops officer Joannides, they began calling the press to say they had proof that Kennedy had been killed by a Castro supporter. Within a day, Joannides-funded AMSPELL agents had generated the first J.F.K. conspiracy theory to reach public print: Oswald and Castro were the “presumed assassins.”

Under interrogation in Dallas, Oswald denied killing Kennedy. 

REPORTER: Did you shoot the President? 

OSWALD: No. They’ve taken me in because of the fact that I lived in the Soviet Union. I’m just a patsy! 

The next day, Oswald was being transferred to another jail when Jack Ruby, a former foot soldier in Sam Giancana’s Chicago crime syndicate, stepped out of the crowd and shot him dead. Oswald never got a chance to explain himself. 

Six decades later, the CIA is still reluctantly coughing up new information about these baffling events. The latest J.F.K. files establish that Oswald was not a “lone nut” in the eyes of the US intelligence service. To the contrary, he was a known quantity.