She may have been one of the bravest and best-placed American spies in the history of the Cold War, but few people outside the CIA know the mysterious story of June Cobb.
The existing information in the spy agency’s declassified files depicts Cobb as an American Mata Hari—an adventure-loving, death-defying globetrotter who moved to Cuba to work for Fidel Castro, the country’s newly installed strongman, then found herself recruited to spy for the CIA after growing disenchanted with Castro’s revolution. The era’s rampant sexism is obvious in her job evaluation reports: Cobb’s CIA handlers wrote down speculation about her sex life and her failed romance in the 1950s with an opium farmer in the jungles of South America. And the reports are filled with appraisals of Cobb’s looks, noting especially her fetching blue eyes. “Miss Cobb is not unattractive,” her CIA recruiter wrote in 1960. “She is blonde, has a slender figure, although she has a somewhat hard look, making her appear somewhat older than her 33 years.”
According to another, undated evaluation, she had a “wiry” figure but had been attractive enough to catch the Cuban dictator’s eye. Cobb, the report said, was reputedly “a former girlfriend of Castro’s.” True or not, she was close enough to get a job on the Cuban dictator’s senior staff in Havana in 1960, the perfect perch to spy for the CIA. Cobb’s agency work in Havana and later in Mexico leads us to the most puzzling aspect of her life—that she later found herself drawn deeply into the mysteries of John F. Kennedy’s assassination. After the murder, she reported to her CIA bosses that she had identified a trio of witnesses who could tie Kennedy’s assassin, Lee Harvey Oswald, to Cuban diplomats and spies in Mexico City, where Oswald had traveled just weeks before the assassination.
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