Well this is embarrassing.
dg1952's comment sent me over to the Classic site to look at their (better) pic of the mast bearing. Doh!
I was trying to get the bearing only out, not the larger cup in which it sits. Once I realized my mistake it took all of two minutes to get it out. It fits flush enough that I didn't notice the difference between the top lip of the mast bearing and the top of the steering column.
Oh, and there's the stub of a wire attached. Imagine that.

OK, I'm going to go sit on a stool in the corner now, wearing that pointy hat.


A VW guy trying his hand at a '59 LB fs. Lots to learn, but it's about the journey.