Scott, if it was my tree, especailly a 50 yr old plant, I'd air-layer. Do it in sections..Since it's 14', do so in a little over 3' sections..After each section roots, add to the pot..instead of one cane, she'll have three at 3' heights.
Some people just cut the trunk, root, then add to soil. This will also work.
Because of its age, and time spent w/you and your wife, I'd not rid it, be it sell or discard. Good luck, Toni

I was reading about air layering at this website:
http://www.extension.iastate.edu/Publications/PM268.pdf
And the document they wrote seems to imply that dracaena plants *require* this type of treatment. But information I've seen elsewhere on this site implies that you don't need to go to all that trouble. Some owners say they are very hardy plants, and you can just cut them down and stick them in the dirt. I'm confused about all this information. One consideration is that my brother and his wife are being very kind to care for the plant while we are relocating to Seattle from Chicago, but eventually we need to ship this plant to Seattle. Maybe we just cut it down when the time comes and stick it in our carry on luggage? Air layering requires alot of work, and creates an unsightly plant for a period of time. I am hesitant to put that burden on my brother's family as they care for our plant. And I'm not sure they would feel comfortable doing plant surgery. Oh boy... What is the consensus opinion? Is air layering really our only viable option?

http://www.leevalley.com/garden/page.aspx?c=2&p=46938&cat=2,47236

Someone posted this site a while back.

A 50 year old treasure would be hard to simply "wack off". I think there are smaller devices like this one that might be more attractive.

Good Luck Diane

i used to have a Janet Craig & still have a corn plant. the cane's look identical!

so i don't see why you can't just whack it into lengths, apply rooting horomones to the bottoms of the pieces, & stick it into dirt.

granted it's current height is daunting, BUT! this just means longer pieces or more short pieces.

i'd decide the number & height of the pieces i wanted. assemble pots & dirt & rooting horomone is very cheap.

whack it & stick the bottom ends of each piece into water then the rooting horomone, then into dirt, mounding up the dirt around it to support itself while growning new roots.

in a few weeks you'll have new growth at the cut edges & roots holding it up.

lil.