Usually you tie another wire or string on it before you pull it out, so as to be able to pull it back thru. If the mast bearing is new, it should be good. If wire not pinched on install, or damaged during install, I don't know what could be wrong. I assumed it was the add-on wire that was the culprit. As wire leaves the column, it should be protected and tied up away from rubbing on sharp edges. The upper mast bearing is a combo bearing and electrical slip ring. It is a pretty straight forward install. Be sure you don't have the steering wheel or something else touching the copper slip ring portion of the bearing. Maybe you can do a continuity test on just the bearing wire by disconnecting the add-on wire, if you can reach in and test.
Where do you have the wire exiting the column? I believe that is near the top of column?
