1984
Beginning in August 1984, a small group within the US government, in the Iran-Contra affair, arranged for the indirect transfer of arms to Iran, as a means of circumventing the Boland Amendments that were intended, in part, to prevent the expenditure of US funds to support the Nicaraguan Contras. Since the arms-for-hostages deal struck by the Reagan Administration channeled money for to the Contras, the legal interpretation of the time was that the CIA, as an organization, could not participate in Iran-Contra.
The relationships, first to avoid the Boland Amendment restriction, but also for operational security, did not directly give or sell U.S. weapons to Iran. Instead, the Reagan Administration authorized Israel to sell munitions to Iran, using contracted Iranian arms broker Manucher Ghorbanifar. The proceeds from the sales, less the 41% markup charged by Ghorbanifar and originally at a price not acceptable to Iran, went directly to the Contras. Those proceeds were not interpreted as U.S. funds. The Administration resupplied Israel, which was not illegal, with munitions that replaced those transferred to Iran.
While Director of Central Intelligence (DCI) William Casey was deeply involved in Iran-Contra, Casey, a World War II Office of Strategic Services (OSS) clandestine operations officer, ran the Iran operation with people outside the CIA, such as White House/National Security Council employees such as John Poindexter and Oliver North, as well as retired special operations personnel such as John K. Singlaub and Richard Secord
Read more about this topic: CIA Activities In Iran