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In the end of the film,

Winston

shoots John Wick and he falls off the roof.

Seeing that,

Charon

says, Well played, sir (?).

I did not watch the movie in English, and I am a bit confused if some meaning was lost in translation (and whether it was indeed "well played" in the original).

What of the following actually happened?

  • The shooter actually tried to kill John Wick, which the other person understood and approved.
  • The shooter made it look like he is trying to kill John Wick, which the other person understood and approved.
  • The shooter actually tried to kill John Wick, but the other person understood it as a well played ruse which they approved.
  • The shooter made it look like he is trying to kill John Wick, but the other person understood it as an honest assassination attempt, which they approved.
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    Not enough for an answer, but judging from Winston's reaction when he learned what happened to John, it seems like it was planned that way, so the second option applies. It is confusing though, because John must have known and therefore acted it out. Bold strategy, if true.
    – Ian
    May 31, 2019 at 8:08
  • I suspect it's intended to be deliberately ambiguous, especially given the very ending of the movie, so we may have to wait a few years for Chapter 4 to find out the answer. Personally I think John was in on the plan and that the adjudicator thought Winston was actually trying to kill John (your scenario #4).
    – Anthony Grist
    May 31, 2019 at 14:41
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    @AnthonyGrist The other person is not the adjudicator, but I agree that it might be intentionally ambiguous. I personally tend to think it is #3, given the very last words John Wick says on screen.
    – GSerg
    May 31, 2019 at 16:00
  • I'm voting to close this as primarily opinion-based because this will definitely be revealed in a future work (John Wick 4). Can't see Winston and Charon's subtlety here other than being intentionally ambiguous.
    – Jenayah
    Aug 16, 2019 at 19:21

2 Answers 2

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High Table, and Adjudicator, knew that Wick won't kill Winston. What's worst they knew that Wick knew who master of the assasins was. So they only had one chance of "bribing" Winston to shot John at close range. If the Adjucator (or anyone else) would kill Winston they would face John. And they learned that it might not well good for them.

Now, Winston shoot John and Adjucator Well played, sir is approve of his decision. He sacrificed the pawn to save the king (or bishop or whatever position Winston held). But we, and Winston, knew two things. First is bullet proof suit. Second, when meeting Winston back at Continental, Winston gave Jonh the gun which he then returned. Combining it with his fake suprise when John body is not found in the alley we can safely assume that this was their plan.

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It is clear that Winston has some sympathy towards John Wick. He left him time to escape before launching the excommunicado order, treated him kindly since the first episodes ; further John decided to not kill him when he could.

On the other hand he has to show fealty to the "High Table" order if he wants to maintain the power he has over the Continental establishment (and in the organization), and in particular he has to prove this fealty in front of their emissary the Adjudicator that is present during that scene.

There is therefore strong evidence that shooting at John at that calculated angle was a trick to make sure both him and John would survive the situation.

Did Winston have other motives? And did John understand that this gesture was to protect him? are questions that will certainly be answered in the next episode of the franchise.

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