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Oh, he has to die.
~ Winston betraying John
Have a drink, and relax... for now.
~ Winston to John Wick.

Winston is the deuteragonist in the first 2 John Wick films, serving a small but important role in every film. In John Wick: Chapter 3 - Parabellum, he is a major antagonist, showing that while he is a friend to John Wick, he is still ahigh-ranking member of the Continental, and does what he has to do to those who break its laws.

He is portrayed by Ian McShane.

Biography

John Wick

In the first film, Winston makes a short appearances at the start of he film. When John appears in the Continental hotel he goes to the bar to search for Iosef after Iosef robbed his car and in the process killed his dog. Winston greets him as they are old friends, but tells him that such businesses aren't allowed in the hotel, so he's better off just relaxing.

Winston returns later in the film when Ms. Perkins kills an old assassin and friend to John named Harry, which breaks against the Continental's rules of not killing people outside of the organization. Winston confronts her and calmly tells her that her membership in the Continental has been revoked, in which his henchmen quickly execute her and walk away.

John Wick: Chapter Two

Winston first appears when Santino D'Antonio discussed with him about John Wick and what to do, and Winston states that Santino has put himself in a dangerous situation as he's gotten Wick back in his old life as an assassin, and considering Santino's put Wick in a bad situation as well, he might be killed by him.

At the end of the film Wick confronts Santino while he's eating. Santino taunts Wick to get him to kill him which would effectively ruin Wick's life even more. Although Winston tries to convince Wick not to do it, he kills Santino anyway. In the final scene of the film, Winston and John meet after John broke a rule in the Continental, and every assassin in the Continental will now be notified about that, and will be ordered to execute him. However, he gives John a one hour lead, as they are after all old friends.

John Wick: Chapter Three - Parabellum

Winston returns in the third film. Winston and the High Table meet John Wick at a parlay and discuss what they have to do about the situation, and they actually come to an agreement to spare him. However, after the agreement, Winston goes out and shoots John so that he falls down, though not fatally. It is unknown if he genuinelly tried to kill John or did it non-fatally purposely. It was soon revealed that John Wick barely survived the gunshot upon being taken in to Bowery King.

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