Help! Brown turkey fig tree needs pruning

Have a fig tree that has grown to about 20' tall and it needs pruning:
1) to get it off a flat roof
2) bring it back to a height that I can reach more easily

Should I begin pruning NOW or should I wait until winter? 
Know that if we have a really bad freeze, it will die to ground and maybe even kill the tree. The past 2-3 winters here have been really mild so nothing has hurt it.

How much should be pruned at one time??

An organic farmer in our area pruned his Brown Turkey within the last month or so.  He cut every branch right back to a fig.  Then he planted all those trimmings and is growing new trees for sale in the future.

Is your tree in the ground in zone 7 or zone 6?  I ask because I have one and can't decide whether to put it in the ground or leave it in it gigantic pot.

CC

CapeCoddess - we're in Zone 7 and I did take a chance on removing this fig from a pot to the ground, but we are protected by other houses around us.

Thanks for the info about your neighbor.
THe tree, looking out our back door:


Looking at the tree from our porch roof.  See where the tree is pushing down the railing.


Closeup of some figs/tree:

Unfortunately this really bad past winter caused the fig tree to die and now it is time to saw up the remains.

@walshevak wrote:

@Judy McConnell wrote:Unfortunately this really bad past winter caused the fig tree to die and now it is time to saw up the remains.

Don't count it out yet.  Cut down almost to the ground and see if new growth will come up from the root.  I dug up and planted a fig from a neighbor's house late last summer and thought it died even before the cold hit.  Yesterday I was getting ready to dig it up and put a blueberry bush in its place when I spotted a tiny bit of growth.  So I'm waiting for another month.

Kay

Hmm.  Interesting that this came up as I was perusing websites about turkey figs right before coming onto the forum.  I was thinking that mine is dead from exposure due to that lousy winter we just had.  But then I decided to pull it out of the pot and trim the roots and re-pot it into a smaller pot to see what happens.  There's also a very slight chance that a couple of the cuttings I planted when pruning this brand new plant last fall (to within an inch of its life) have taken.  I probably shouldn't mess with any of them but I really want to know if anything survived. 

The only thing stopping me are the gusts to about 40 that we are experiencing right now...grrrr...
 
Judy, I vote with Kay to cut the tree and leave the roots.  It was such a beauty and looked so healthy.  If it regrows you have another chance at keeping it smaller.
CC

THanks, Gals - I'm going to give the tree until 6/1 because when I cut off a branch there was green (pholem?) inside the bark.  Reading indicated that this "might" indicate the tree is still alive so I'll wait a bit.

So I waited and waited and discovered little green sprouts ALL over the base of the once beautiful fig tree.  Had a local man cut off the dead branches and this is what was left:


Should I break off the weaker sprouts or just leave things alone?

Judy, that's quite a comeback your tree is making! Mine is regrowing also after that awful winter. I thought for sure it was a goner. Just this morning I was trying to decide about whether to cut off the old branches or not but landscaper neighbor friend of mine told me to wait as they will probably sprout. So I'm going to wait.

Still haven't made up my mind about whether to plant it in the ground or not. I'm thinking if it can make it thru that last winter in a pot it will probably do fine in the ground. Any thoughts?

CC

CC - mine lived in a pot for its first five years and then it went into the ground.  It really took off and grew and grew.

My guess is that yours is small enough that you will be able to cover it with blankets, straw bales, etc. this coming winter.

One thing that I didn't do was keep the plant small enough to protect it during winters and ended up paying the price.