One of the darkest, most controversial chapters in this saga was the Iran–Contra affair, a secret, illegal web of arms deals, hostage diplomacy, and foreign insurgencies that nearly collapsed the Reagan presidency.
As tensions soar in the Middle East following US strikes on Iranian nuclear sites and Iran’s unprecedented move to close the Strait of Hormuz, the long and complex history between the two nations is back in focus. The US–Iran relationship has swung between covert alliances and open hostility, shaped by decades of geopolitical manoeuvring.
One of the darkest, most controversial chapters in this saga was the Iran–Contra affair, a secret, illegal web of arms deals, hostage diplomacy, and foreign insurgencies that nearly collapsed the Reagan presidency.
In the late 1980s, at the height of Cold War anxiety, the US found itself entangled in a geopolitical paradox. Publicly, it condemned terrorism and opposed Iran, which had severed ties with Washington after the 1979 Islamic Revolution and the fall of the Shah government. But behind closed doors, a different reality played out. While Iran was at war with Saddam Hussein’s Iraq, a country the US publicly supported, Washington quietly struck a deal with Tehran. In exchange for American missiles, Iran was expected to help secure the release of US hostages held by Hezbollah in Lebanon.
The plot thickened with an unexpected detour to Latin America. Profits from the arms sales to Iran, roughly $48 million, were funnelled illegally to the Contras, a right-wing rebel group fighting Nicaragua’s Marxist Sandinista government. This direct violation of the Boland Amendment, which prohibited US funding for the Contras, was orchestrated by figures deep inside the Reagan administration.
At the heart of the operation were Lieutenant Colonel Oliver North, Vice Admiral John Poindexter, and a secretive network known as the Enterprise, headed by retired Air Force Major General Richard Secord. Together, they ran a covert supply chain outside the bounds of law and oversight.
Missile systems such as TOW and Hawk were covertly shipped to Iran via third-party countries like Israel. Hostage releases followed, though not consistently. Meanwhile, the funds travelled back through unofficial channels to bankroll the Contras. This entire 'shadow war' was hidden from Congress and the American public.
The operation began to collapse in October 1986, when a cargo plane supplying the Contras was shot down over Nicaragua, exposing the covert network. Then, a Lebanese newspaper revealed the arms-for-hostages arrangement. The US media pounced. Public outrage surged, and Reagan’s approval ratings nosedived.
Televised hearings in 1987 placed Oliver North front and centre. Though multiple officials were indicted and convicted, most were either overturned or pardoned, notably by President George HW Bush in 1992, who himself had served as Reagan’s vice president. Key figures like Caspar Weinberger and Robert McFarlane escaped jail time, while North became a polarising symbol of loyalty and lawbreaking.
The Iran–Contra affair wasn’t just a scandal, it was a blueprint for how far executive power could go unchecked. It exposed the fragility of democratic accountability and redefined the boundaries of foreign policy secrecy. While Reagan survived the fallout, US credibility as a moral authority took a lasting hit.