Putting an aftermarket ad Chevy pick up wheel on a flaming river column do I have to drill a hole for the wire to come through the contact/ horn button holder? Picture below.
no, you need the correct contact assembly that does not have a wire, it just has a piece that contacts the back side of the button. This might or might not be the right one for that steering wheel.
The other problem is that they changed the contact ring below the steering wheel. If we could see what you have there...it might help...but I think it could be that you need to remove the wire, and add a long spring to make contact. But hard to say without seeing what's there. Older columns had the contact ring on the top of the column tube, later ones had it in a plastic housing under the steering wheel. The change happened in the mid 60s.