Steering column rebuild 67 barracuda

After some more attempts.........Is it possible that the square headed bolt is a friction piece and is supposed to be 'cocked'? kind of a 'jam it up' situation? I have looked at the factory manual but to no avail.


The service manual says that its 'inch lbs' of tightness so it doesnt take much but I question weather its supposed to hook the hole or act as a 'jam'.