former girl friend jenny miles

Today in History: Capture of Cuban “Mata Hari” Led to Spy-Diplomats’ Expulsion 1

Tags: Cuban Mission to the United Nations (CMUN), Directorate General of Intelligence (DGI), FBI, Jennifer Miles, Orlando Prendes Gutierrez, Rogelio Rodriguez Lopez, South Africa

October 9, 1970:  Two Diplomats from the Cuban Mission to the United Nations (CMUN), Counselor Rogelio Rodriguez Lopez and First Secretary Orlando Prendes Gutierrez, left the US.  The spies had been given 48 hours to leave based on their role in running Jennifer Miles against several US government officials.  An administrative officer at the South African Embassy in Washington, Havana had tasked Miles to establish and maintain access to influential officials and provide detailed information on their personal attitudes, strengths and weaknesses, and unique characteristics.

Following a joint South African-FBI investigation, Miles had been detained for questioning on October 4th.   She quickly confessed and cooperated fully with the FBI. Based in part upon this cooperation, she was subsequently allowed to return to South Africa.

Rodriguez and Prendes were the only Cuban diplomats expelled during the 1970s.  Rodriguez began his CMUN tour in mid-1969, while Prendes arrived that September. According to a declassified CIA report, Prendes - the DGI Centro Chief – handled Cuban sources in the Casa de Las Americas, Puerto Rican extremists, a Cuban exile group, and the Dominican Popular Movement (MPD).

This Date in History: Sloppy Tradecraft Dooms Cuba’s Mata Hari 1

Tags: FBI, Jennifer Miles, South Africa

July 5, 1969:  Cuban agent Jennifer Miles loaded her “dead drop” with her latest progress report.  In her case, the dead drop was a loose brick in the wall of a building.  On this occasion, however, the building superintendent found her dead drop and notified the FBI.  Based on details provided in her progress report, the FBI identified Miles as the likely spy within 48 hours.   However, the Bureau did not know for whom she was spying.  On July 9, 1969, the FBI placed her under surveillance. 

Strikingly beautiful, Miles was tall, blue-eyed, blonde, and captivating.   She used her duties as a clerk typist at the South African Embassy in Washington, DC to meet young diplomats who invited her to their embassy parties.  She then used these venues as a means to spot and assess potential American targets.  The FBI, which partnered with South African Intelligence on the investigation, monitored her activities until October 1970.  When confronted about her espionage , she quickly confessed and cooperated fully with her FBI debriefing.  Based in part upon this cooperation, she was later allowed to return home to South Africa.

Editor’s Note:  A “dead drop” allows two individuals to use a secret location to leave materials.  Its use permits a spy-handler and his agent to exchange objects and information without having to meet. 

Jenny The Blond Spy

Jenny and me at the Majesties Cellars in Johannesburg, 1971




In 1970 or 1971, my publicist jerry wald asked me if i wanted to do a photo shoot for some advert in johannesburg, south africa. apparently i was to meet with jennifer, the setting was to be an elevator in an expensive hotel. i was to hold a brief case, and open it at the directed time, of which the case held $1.0 million us dollars. in fact it was old federal dollars and looked real. then to pass the case to jennifer. thats how we met. jenny eventually became a reporter for the sunday times in cape town, and in 1973 i left south africa for london.