North was on the National Security Council in the White House at the time, not the Pentagon. Congress (controlled by D's) had passed the treasonous Boland Amendment which prohibited aid to the Contra's in Nicaragua.
He sold (older) TOW missiles to to Iran (in the middle of the Iraq-Iran War) to encourage them to help get hostages in Lebanon released and the proceeds were used to fund the Contra's. While I'm not happy that he sold missiles to Iran, at least it wasn't pallets of cash and we were playing both sides as we were also selling weapons to Iraq.
He's been very active with NRA for many years now, and is very, very pro-2A. One of the best speeches he's given at an NRA Annual Meeting.
https://www.youtube.com/watch?v=MLOjIKt7wOk