Turns out the emergency brake was stil locked up on the drivers side. Took the drivers side cable out and was able to get the passenger side drum on with a little effort. I spent some time trying to get the cable to release and it looks like it is beyond repair.
Any ideas on a cheap method? I found a cable on Chev's of the 40's that looks like the components are correct... but for $90. I figure on hitting up the hardware store to see what options I can come up with.