Despite no official diplomatic relations between the United States and Iran and continued strain between the countries members of President Reagan’s administration illegally sold weapons to Iran to illegally fun the Nicaraguan Contras, a revolutionary group fighting the oppressive leader of the country. They also hoped that the arms sales would convince Iran to release US hostages in the country.
It’s unclear what President Reagan knew, but that’s how it’s supposed to work. Even if the President knows he gets cover. Oliver North knew everything though, and he testified endlessly in front of congress about his role in the Iran-Contra affair. Ultimately it was a bit of a black eye on the administration but they did secure the release of several hostages so perhaps it’s not all bad. Either way it ended up being a smaller deal than you might imagine if you were there when it happened.