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. His family disapproved of the relationship, considering Cobb beneath his station. They were later engaged. Cobb took extension classes with Olozaga at the
National University in
Mexico City in 1947. a rare tropical disease. She returned to the United States for treatment, spending several months hospitalized at
Mount Sinai Hospital in New York City. After she recovered, she spent five months working at the hospital as an administrative assistant for Dr. Isidore Snapper. In early 1952, Cobb began a relationship with the
Federal Bureau of Narcotics. During the summer of 1952, she was employed with
Time magazine in their letters department. Cobb then moved to Chicago and worked as a secretary again for Snapper, who was now the director of medical education at
Cook County Hospital. Cobb returned to New York City in 1953 and found work as an interpreter and translator. Her friend Warren Broglie, manager of the
Waldorf Astoria, referred clients to her. Towards the end of 1953, Cobb worked briefly for
Foster Wheeler, a firm that was building a refinery in Colombia. In the summer of 1954, Cobb was treated for
agranulocytosis at
Beth-El Hospital in New York. By 1955, Cobb was traveling in Latin America. In 1956, she worked for the Colombian-American Culture Foundation in Medellin and taught briefly at the American school. In December 1956, the Olozaga brothers were arrested in Havana for possession and distribution of
heroin. 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. Cobb had traveled with the brothers to Havana to help them sell several grams of heroin and several ounces of cocaine. The brothers were released quickly, owing to their family connections. 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. FBN agent George Gaffney later recalled that the 1957 operation originated in New Orleans when "a woman with CIA connections offered information" to an agent. In 1957, Cobb briefly worked as a secretary for county attorney Ralph Haynes. 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. By 1959, Cobb had moved to New York City. She lived briefly at the Hotel Iroquois. ==Involvement with Cuba==