Following the 1959 Cuban Revolution, Posada fled to the United States. There, eager to join the war against Castro, he joined the US army, receiving explosives training at the notorious School of the Americas in Fort Benning, Georgia, and rose to the rank of second lieutenant.
According to agency records, Posada’s first contact with the CIA was in 1961, when he was recruited and trained for the failed Bay of Pigs invasion. He was commended by the Agency as “strongly anti-Communist” and deemed “of good character, very reliable, and security conscious.” Posada remained on the CIA payroll from 1965–1976. He spent several of those years in Venezuela, working in the state intelligence service.
1976 was a big year for Posada. CIA documents implicate him in the assassination of Orlando Letelier, the former foreign minister of Chilean president Salvador Allende, in Washington, D.C. Shortly thereafter, he was imprisoned in Venezuela for his role in the Cubana airline attack, the largest act of terrorism to strike the Americas.
But Posada was connected, and the war on communism was calling. After several failed attempts, he escaped jail in 1985 with help from his Miami-funded network of anticommunist Cuban exiles, including fellow Bay of Pigs veteran and CIA operative Felix Rodríguez. They flew Posada to the Ilopango air base in El Salvador.
In 1985, Ilopango was humming with activity. As the US Military Group in El Salvador supported the homicidal military regime’s counterinsurgency campaign against the leftist Farabundo Martí National Liberation Front (FMLN), CIA operatives were also using the base to clandestinely smuggle arms to the counterrevolutionary paramilitary forces fighting to overthrow the Sandinista government in Nicaragua — a practice expressly outlawed by the US Congress.
After a couple of months lying low, Posada joined Rodríguez in the Ilopango Contra supply operation. Rodríguez, in turn, had been recruited by Lieutenant Colonel Oliver North, a top aide on Reagan’s National Security Council. The project was known as “the Enterprise.”