グレナダ侵攻
Gillespie spent over thirty years in the United States foreign service as a specialist in Latin American and Caribbean affairs. Many of his foreign assignments were to Latin American countries experiencing domestic strife. For example, Gillespie served as the interim Chargé d'Affaires during the 1983 United States Invasion of Grenada as well as in Colombia from 1985 until 1988, when the government sought to crack down on the Illegal drug trade in Colombia and the Colombian drug cartels. Gillespie often received daily death threats from the Colombian cartels.