Сент-Джорджес
Gillespie served as the deputy Assistant Secretary of State for the Caribbean and deputy for operations in the State Department's Inter-American Affairs Bureau from 1983 to 1985. Through this position he oversaw the opening of the first American embassy in St. George's, Grenada. Gillespie was involved in the planning of the invasion of Grenada in October 1983. It was the first major U.S. military operation since the Vietnam War. The invasion by the United States and several Caribbean nations led to the overthrow of the Grenadan military government which had executed Grenadan Prime Minister Maurice Bishop. Approximately 100 people, including 19 members of the United States armed forces were killed in the invasion.