She was the first CIA asset to relay an account of Lee Harvey Oswald having attended a twist party in Mexico City weeks before the assassination of John F. Kennedy.
Cobb was fluent in Spanish, notably translating Castro's "History Will Absolve Me" speech and former Guatemalan president Juan José Arévalo's short story The Shark and the Sardines.
[1] After leaving the University of Oklahoma, Cobb traveled to Mexico, where she met Rafael Herran Olozaga, who was from a wealthy and politically connected Colombian family.
Both his great-grandfather, Pedro Alcántara Herrán, and his great-great-grandfather, Tomás Cipriano de Mosquera, had served as Presidents of Colombia.
The pair were apprehended by Cuban law enforcement officials, with the assistance of US Federal Bureau of Narcotics (FBN) agents, a day after Cobb had left Cuba for Coral Gables, Florida.
[13] In a joint operation of the FBN and the Colombian Intelligence Service, the brothers were arrested again in Medellin, Colombia in February 1957 for running a cocaine laboratory on their parents' estate.
[3] For a time in 1958, Cobb was acquainted with Dimitre Dimitrov, a Bulgarian politician who had been imprisoned in Greece and interrogated by the CIA as part of Project ARTICHOKE.
[16] Cobb visited Havana in February 1959 and later recounted meeting with Fidel Castro's Minister of Health regarding their campaign against vice and cooperation with doctors from Bolivia, Peru, and Colombia against the use of coca leaves.
[19] Cobb disagreed with Castro openly over his turn to authoritarianism and Marxism, her anger becoming evident as the Communist influence on him became obvious.
Following a brief conversation, Cobb agreed to arrange meetings with Cuban officials for Hermsdorf and Der Spiegel correspondent Claus Jacobi.
[25] Cobb made a verbal agreement to work for the CIA and returned to Havana on June 7, and was to be paid 200 Cuban pesos per month plus expenses.
Hermsdorf asked Cobb to monitor the activities of the chief of Prensa Latina and the head of the Free China News Agency.
[26] In a June CIA memo from Hermsdorf, he wrote "If Miss Cobb can be controlled and accepts steering, it would perhaps be desirable to mould her into a long-range asset by having her become very cozy with the communist leaders and become, overtly, ever more 'rabid' about the revolutionary movement.
[28] While in Havana, on more than one occasion, Cobb met with CIA operative David Sánchez Morales at the house of Geraldine Shamma.
[29] Cobb's first CIA operation involved befriending CBS newscaster Richard Gibson, a co-founder of the Fair Play for Cuba Committee.
[30] Cobb determined that Gibson had made a trip to Cuba, met with Castro and Osvaldo Dorticós Torrado, and received money for operating expenses and to maintain the FPCC New York office.
[32] Around 1961, alongside Raul Osegueda, Cobb translated former Guatemalan President Juan José Arévalo's 1956 allegory The Shark and the Sardines to English.
[33] From Mexico, Cobb assisted Guatemalan revolutionaries fighting Miguel Ydígoras Fuentes, helping them obtain equipment.
[citation needed] CIA Mexico City cables related that Cobb was deported with Achilles Centeno Perez.
[35] An August 12, 1962, article by Jack Anderson in Parade magazine painted Cobb as a "soldier of fortune", detailing her time working for Castro and her involvement with drug trafficking in Latin America.
[29] Warren Broglie, who was then managing Hotel Luma, passed information to Cobb that she relayed to station chief Winston M.
Following the assassination of John F. Kennedy by Lee Harvey Oswald, and the release of the Warren Report, Cobb was privy to a conversation between Elena Garro, her sister Deva Guerrero, and her daughter.
[39] In 1965 and 1966, Cobb set up Milton Abramson, a New York-based drug trafficker, Adela Castillo, and others for arrest by the FBI in the United States.
[2] From 2009 to 2011 independent filmmaker Mary Haverstick was researching a documentary she wanted to make about Jerrie Cobb, an American pilot and aviator who was also part of the Mercury 13.
When Haverstick suggested that June Cobb had flown a plane waiting at Redbird Airport, Dallas, on November 22, 1963, the day President Kennedy was killed, which had been standing on the runway for an hour with engines running, and was rumored to be the get-away plane for Lee Harvey Oswald, Jerrie Cobb reacted strongly, but gathered herself and said, "I was at the Redbird Airport."
[40][41][42] After falling ill, June Cobb lived with family in Houston, Texas, for a time until she sustained a head injury in a household accident and was eventually transferred to the Manhattan senior center prior to her death on October 17, 2015.
Some of the Warren Commission's declassified files indicate that the CIA, in the late 1970s, refused to help House Select Committee on Assassinations investigators locate Cobb for an interview about Oswald's activities in Mexico.