Winston wasn't aiming to kill John Wick, he just wanted to keep up appearances in front of the Adjudicator.
This is foreshadowed early on in the film when John Wick shoots the doctor in order to protect him from the High Table.
Yes he knew the bullets would not penetrate his suit, but come on! Falling several stories slamming into balconies and other building profusions before slamming onto cement? And still alive even after being tossed into a shopping cart without bracing his neck. No armor can protect from a fall.
shareIt was one hell of a Hail Mary play. There was no way Winston could have been sure JW would survive.
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