David Phillips was a failed actor turned expatriate newspaper publisher in Santiago, Chile when he was recruited into the CIA in the early 1950s. He made his mark fast. In 1955, he won a Distinguished Intelligence Medal, one of the agency’s highest honors, for mounting deceptive radio broadcasts in the CIA’s overthrow of the democratically elected government of Guatemala in 1954.
After that his CIA career took off. With Howard Hunt, Phillips served as propaganda chief in the CIA’s failed effort to invade Cuba at the Bay of Pigs In April 1961. When he was assigned to Mexico City in 1962, station chief Win Scott described him as “the finest covert action officer I have ever met.”
After JFK’s assassination, Scott was not so complimentary and I suspect the reason why was Oswald’s curious handling of Oswald. .(I tell the story in my biography of Scott, Our Man in Mexico. Buy it here.)