On l7 April 1961, a force of Cuban exiles, trained and equipped by the Central Intelligence Agency, invaded their homeland at the Bay of Pigs. Eighty Air Guardsmen, serving as civilian volunteers, trained the exiles to fly old B-26 bombers and transports. The Guardsmen volunteered for combat missions after the exiles lost two B-26s on D-Day. The Bay of Pigs Invasion was an unsuccessful attempt to overthrow the Cuban government as well capture the premier of Cuba, Fidel Castro. Increasing friction between the U.S. and Castro's leftist regime led President Dwight D. Eisenhower to break off diplomatic relations with Cuba in January 1961.

On April 17, under newly elect, President Kennedy authorized a surprise act on the island of Cub. The armed Cuban exiles about 1,200 armed with U.S. weapons to invade Cuba. The exiles, landed at the Bahía de Cochinos (Bay of Pigs) on the south coast of Cuba only to be met by Castro's army. The failure of the invasion seriously embarrassed the Kennedy  administration. Many felt that the CIA set up the Kennedy administration to look bad. Kennedy was so mad he was planning on disbanding the CIA.