He should get the frame checked for straight. I remember working on a 65 Custom Sport where the column bearings were all shot. Once the bearings were replaced the column wouldnt line up straight to the steering box. I finally got it mounted but you could see the rag joint twisting almost binding while turning the steering. It turned out the frame was bent and the binding is what destroyed the column bearings.
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'68 Parisienne 2+2 Convertible Matador Red (Resale Red but not for sale).