JFK Riddles: Lee Harvey Oswald & the Mysterious Mexico Trip

Thomas C. Mann, America’s then-ambassador to Mexico City, blurted out hours after JFK’s death that he was certain shooter Lee Harvey Oswald didn’t act alone. So what did Mann know and why was he ordered to keep quiet?

SPYSCAPE followed the Oswald riddle to Mexico City in 1963 when the capital was a pinata of rogue spies, revolutionaries, and potential assassins. Here are some of the secrets we uncovered:

The Lee Harvey Oswald CIA files in Mexico filled more than five suitcases
Oswald’s Mexico CIA file was so big it filled more than four suitcases

1. The CIA’s Oswald file in Mexico City alone filled four suitcases 

Oswald arrived in Mexico in late September 1963, just weeks before President John F. Kennedy’s assassination. During his six-day stay, Oswald visited the Cuban and Russian embassies trying to secure travel visas to visit Havana and the Soviet Union. All the while, the CIA recorded him and logged Oswald’s movements.

JFK Riddles: Lee Harvey Oswald & the Mysterious Mexico Trip

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Thomas C. Mann, America’s then-ambassador to Mexico City, blurted out hours after JFK’s death that he was certain shooter Lee Harvey Oswald didn’t act alone. So what did Mann know and why was he ordered to keep quiet?

SPYSCAPE followed the Oswald riddle to Mexico City in 1963 when the capital was a pinata of rogue spies, revolutionaries, and potential assassins. Here are some of the secrets we uncovered:

The Lee Harvey Oswald CIA files in Mexico filled more than five suitcases
Oswald’s Mexico CIA file was so big it filled more than four suitcases

1. The CIA’s Oswald file in Mexico City alone filled four suitcases 

Oswald arrived in Mexico in late September 1963, just weeks before President John F. Kennedy’s assassination. During his six-day stay, Oswald visited the Cuban and Russian embassies trying to secure travel visas to visit Havana and the Soviet Union. All the while, the CIA recorded him and logged Oswald’s movements.

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The CIA’s legendary Mexico City chief of station, Winston ‘Win’ Scott, collected enough intel to fill four suitcases and several large cartons with memos, photos, and tape recordings, according to Jefferson Morley’s The Ghost.  The US were spying on the Soviet Embassy with ‘multi-line phone taps, three photographic sites, a mobile surveillance team and a mail intercept operation,’ a CIA document declassified in 2017 explained.

Does Mexico hold the key to JFK's murder?
Mexico may hold the key to the JFK murder

2. Did theWarren Commission get it wrong?

Win Scott’s CIA book manuscript seems to show that the Warren Commission investigators got it wrong. The CIA, FBI, US Embassy, and US State Department spies apparently knew Oswald visited the Cuban consulate in Mexico before JFK’s murder, not afterward.

"Every piece of information concerning Lee Harvey Oswald was reported immediately after it was received to: US Ambassador Thomas C. Mann, by memorandum; the FBI Chief in Mexico, by memorandum; and to my headquarters by cable; and included in each and every one of these reports was the entire conversation Oswald had from the Cuban Consulate with the Soviet Embassy," Scott reportedly wrote in Chapter 21.

Lee Harvey Oswald
Lee Harvey Oswald: Lone gunman or a patsy?

3. Oswald was disorganized and lied hoping to get a travel visa

Oswald was in a flap during his Mexico trip - a far cry from a smooth-talking double agent communicating with his Communist handlers. Oswald’s Spanish and Russian skills were so poor, eavesdroppers had trouble understanding him at times. Oswald repeatedly revisited the Cuban consulate because he didn’t bring a photo for his visa or confirmation of his travel plans. Oswald raised suspicions again by telling Cuban diplomats his Russian visa would be expedited, although he knew approval could take up to four months. 


J. Edgar Hoover
Former FBI director J. Edgar Hoover

4. Oswald may have threatened to ‘kill Kennedy’ at the Cuban consulate

Former FBI Director J. Edgar Hoover wrote a top-secret letter to the Warren Commission in June 1964 revealing that Oswald may have boasted “I’m going to kill Kennedy” while at the Cuban consulate in Mexico. David Slawson, a California law professor and ex-chief investigator for the Warren Commission, believes someone blocked him from seeing Hoover’s letter, according to Politico.

Were Cuban dissidents behind the Kennedy assassination?
Conspiracy theorists think spies may have used Cuban exile groups to communicate with Oswald

5. The Cuban connections in Mexico may be the key to unlocking the mystery

The CIA’s chief of psychological warfare in Miami, George Joannides, bankrolled a Cuban exile group in Florida known as the Student Revolutionary Directorate. The Directorate had contact with Lee Harvey Oswald around the time he visited Mexico, leading to speculation that the group may have been a backchannel connecting the CIA and Oswald.


JFK and Jackie
        Some six decades later, the JFK assassination remains the mother of all conspiracy theories

6. The US Ambassador to Mexico was hushed up

US Ambassador to Mexico Thomas C. Mann told colleagues about suspicions that Oswald didn’t act alone in killing JFK but said the US State Department wasn’t interested. In fact, US Secretary of State Dean Rusk directly ordered Mann to shut down any Mexican investigation that could ‘confirm or refute’ rumors of Cuban involvement, Mann testified to congressional investigators. No reason was given. 


Mexico's Day of the Dead
Mexico’s Day of the Dead celebration

7. FBI officials still have questions about what went down in Mexico

Two FBI memoirs hint that Mexico may unravel the secrets to JFK’s murder. Former FBI Assistant Director William Sullivan described ‘huge gaps’ in the FBI’s investigation in The Bureau: My Thirty Years in Hoover's FBI: “We never found out what went on between Oswald and the Cubans in Mexico City.”

FBI Director Clarence Kelley believes Oswald may have also advocated killing the US president at the Soviet embassy in Mexico. That doesn’t mean Moscow and Havana were behind the assassination, but it would mean communists knew weeks in advance that Oswald, an ex-US Marine with weapons training, was talking openly about killing the US president.

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