Why would the NRA want to associate itself with Oliver North?

Doing that is just dumb.

I know little about North personally and I still think that his exact role in the Iran Contra matter is murky and poorly understood.  But that's the problem. We know that what happened in Iran Contra was illegal and even if North's role was one that was pushed by the Administration all the way to the top (and we still don't know that) North is really not a hero to anyone with a deep intellect.

So, associating yourself with somebody who has a murky involvement with spooky illegality and who is really only admired by the far fight in the shallow end of the pool makes you look dim.

That's not smart.