Possible I suppose, but he was winding out. Once round the corner if for any reason he would have needed to come back he would have wanted it directly behind him to avoid that situation?
Can you get winches with a level wind system then? I've not seen them. The forestry winch I was using the other day was mounted on an A frame with a pulley on the top so no matter where the pull was directed and how much the winched item moved the spool was always at 90 degrees to the rope coming in. Clever I thought.