During the 1950s, there were several initiatives by the CIA to infiltrate communist regimes such as North Korea or China. One of the popular tactics was to simply parachute hundreds of people across the country. The belief was they would start a resistance force and eventually topple the regime from within – of course, as we now know, this never happened and many of these spies ended up facing terrible deaths.
The operation was usually led out of Japan, the office’s cover name was JACK which stood for Joint Advisory Commission, Korea. At the time this was the early days of the CIA, and its role was already confusing for American Military. As they like to say, nobody knew what the spooks were up to. The reports were that the initiatives were quite abysmal at the start, guerrilla forces dropped behind enemy lines were usually located and destroyed fairly quickly.
Despite this the CIA continued to drop people into North Korea, advising that any disruption of North Korean’s military lines of communication was a positive result. We now know they were also trying to set up bases of resistance in North Korea. However, even Korean nationals were usually outed fairly quickly. The thing was the Americans just did not know enough about North Korea in general. For example, reports have come out that many spies were caught and killed just because they had sandals whereas most poor villagers lived barefoot at the time.
Later missions proved more successful, this was achieved by converting shipping vessels into makeshift raiding crafts. It allowed them to insert CIA raiding forces deeper into North Korea and they were able to capture more enemy soldiers or disrupt their military operations greatly. One of the famous boats that embarked on these missions was the Japanese made K-333 trawler. One of their strategies for getting information was to capture railway workers, as they would see where the North Korean army was sending its infantry or tanks.
Much of the success came from building a base of operations on Yo-do island which was very close to the North Korean mainland. Today questions are raised about all the people the CIA simply dropped across the country without any means of a follow-up, the truth is, nobody knows what happened to this would-be spies.