the bearing has a lip that sits flush on top of the mast jacket, you should be able to carefully weasel under it and gently tap it up working around the mast .... that's if you're going to put in a new bearing, in which case you need to tie a string to the wire and when you remove the bearing pull the string up so that when you put in a new bearing you can use the string to pull the new wire down the column, the wire is part of the bearing, not part of the harness .... but if the wire is still sticking out the column down below, you may not need to do anything there, use an ohm meter to check for continuity from the end of the wire to the bearing and if it checks and doesn't look like the insulation is badly deteriorated, just use it
Bill