Originally Posted by
frankenmike
Taking it to a shop is a good idea because they can better assess the situation. I doubt the crown race was installed improperly thirty years ago. Also, I wouldn't be so sure that the picture accurately represents lines that are parallel in real life.
Well, the OP said he got the bike from "a guy". Who knows what that guy was doing to the bike beforehand. Could be some sloppy shadetree home-mechanic who's pounding in headset crown-races with a hammer. In the photo, it's definitely not seated on the fork all the way and definitely isn't square with the steerer either. Pretty simple to fix, but you gotta have the correct tools to install the crown-race correctly.