Ian McShane has addressed John Wick: Chapter 3 - Parabellum's twist ending, which saw his character, Winston, shoot Keanu Reeves' John Wick off the rooftop of the Continental. After a parlay between Winston and the Adjudicator of the High Table, the pair come to an agreement that sees Winston return to power within New York's Continental.
SCREENRANT VIDEO OF THE DAY Ahead of John Wick: Chapter 4 McShane addressed Winston's decision to shoot John by adding context to Winston's thought process while speaking with Digital Spy. He explains that, despite always protecting John because of their friendship, his allegiances are fickle because of how necessary it is for him to appeal to the High Table.
I think the one thing about Winston is, you’ve got, in the first three [movies]… he’s protecting John. He’s trying to do his best.
However, John Wick: Chapter 4 also happens after Winston shoots Wick off the Continental, meaning he will start the film allied with the High Table. It's possible that Winston continues to be allied with them while he's giving John instructions on how he can challenge the Marquis to single combat.
Sadly, it's also possible that Winston is using John's yearning to escape life as an assassin against him, so he will be an easier target for the High Table. While Winston's friendship with John has proven to be strong in the first three John Wick films, he may have to put those feelings aside to save himself from the Table's wrath once more.
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