Okay I figured it out. Might be a useful tip for people who have the same problem. The nut wasn't flush against the crank arm of the pedal. The factory made it lopsided and I never noticed it. So I grabbed a socket wrench cranked it hard until the metal bent and the nut became flushed with the crank arm. If anybody needs any pictures I can post them. There is still a small space that I can't completely close.
