@wonder2wonder said:

At the end, did he really  betray John ?

Or was  shooting, but not killing John, a way to help him escape ?

The scene afterwards between Winston and Charon does imply it was all  a ruse . Or not?

If it was a ruse, based on John's conversation with the Bowery King John was not in on it. 

Hard to say, I really think this will HAVE to come full circle in a John Wick 4!!!!!!!

Sorry, not sure how to put the spoiler bar (the HTML didn't work), anyway, JW was NOT in on what Winston did, but Winton MUST'VE had an idea JW was wearing a bullet proof suit/vest..you can see the shots sparking off of him in fact. The FALL though...dang...how he didn't break his spine is beyond me!

@jorgito2001 said:

Hard to say, I really think this will HAVE to come full circle in a John Wick 4!!!!!!!

Sorry, not sure how to put the spoiler bar (the HTML didn't work), anyway, JW was NOT in on what Winston did, but Winton MUST'VE had an idea JW was wearing a bullet proof suit/vest..you can see the shots sparking off of him in fact. The FALL though...dang...how he didn't break his spine is beyond me!

He didn't fall straight down, it was broken 3 times before he hit the ground, so that saved him. His bulletproof suit also might have helped to cushion the fall.

But still, he is badly hurt. It'll take some time to heal all his wounds and broken bones.

@wonder2wonder said:

@jorgito2001 said:

Hard to say, I really think this will HAVE to come full circle in a John Wick 4!!!!!!!

Sorry, not sure how to put the spoiler bar (the HTML didn't work), anyway, JW was NOT in on what Winston did, but Winton MUST'VE had an idea JW was wearing a bullet proof suit/vest..you can see the shots sparking off of him in fact. The FALL though...dang...how he didn't break his spine is beyond me!

He didn't fall straight down, it was broken 3 times before he hit the ground, so that saved him. His bulletproof suit also might have helped to cushion the fall.

But still, he is badly hurt. It'll take some time to heal all his wounds and broken bones.

Damn, what a way to "break your fall"..at one point he hits a railing which looked ESPECIALLY painful!

As for healing..yes, he REALLY needs to rest & heal up before he takes on the High Table!

I assumed at this point John has a healing factor. Give him, oh, a good month, good as new with all 10 fingers again.

He wasnt in on it. But I think Winston gave him a chance by shooting him in the suit instead of the head. Im sure he knew his suit was bulletproof. He paid him back for not shooting him in the head, but if he died from the fall than so be it.

@OddRob said:

He wasnt in on it. But I think Winston gave him a chance by shooting him in the suit instead of the head. Im sure he knew his suit was bulletproof. He paid him back for not shooting him in the head, but if he died from the fall than so be it.

This was my understanding of the scene. John and Winston clearly didn't have time to 'plan out' this ruse against the Adjudicator, but it did seem like Winston tried to help John out. Inasmuch as one can 'help' somebody while shooting them off the roof of a tall building....

Winston did take a big risk. John might not have survived the fall.