Winston surprisingly seems to be John’s ally in John Wick: Chapter 4, and John Wick: Chapter 3 – Parabellum already indicated Winston’s intentions.
John Wick seems to be joining forces with Winston in John Wick: Chapter 4, and John Wick: Chapter 3 – Parabellum already hinted to that happening. Ever since avenging the killing of his dog in the first John Wick, the legendary Baba Yaga has fought an increasingly desperate war to return to his old life away from being an assassin. It is all set to come to a head with John (Keanu Reeves) and the Bowery King (Laurence Fishburne) going up against the High Table’s forces in John Wick 4.
John and the Bowery King first formed their pact at the end of John Wick 3, after John’s old friend Winston (Ian McShane) seemingly tries to kill John to stay in the favor of the Elder and the High Table, though John ends up surviving. With such a cliffhanger ending to John Wick 3, the idea that John would look to Winston as any kind of ally in John Wick 4 would seem far-fetched at best. However, the groundwork for their team-up teased in the John Wick 4 trailer has been firmly set in place.
Winston Did Not Kill John in John Wick 3 (But Could Have)
In John Wick 3, the High Table’s Adjudicator (Asia Kate Dillon) agrees to peace with Winston and the Continental, but asks what will be done with John himself after his refusal to kill Winston, per High Table orders. After a moment of hesitation, Winston says “Oh, he has to die“, and shoots John in the torso to cause his fall from the roof. However, Winston’s choice to shoot John in his armored torso has led to the theory that Winston was not actually trying to kill John.
Had Winston wanted to ensure John was eliminated, he could have easily shot for his head. Granted, Winston’s strategy seems to be very much a Hail Mary ploy. He had no way to be sure that John would survive the fall, but it is possible that John and Winston might also have devised the strategy together off-screen. In any case, the fact that any possibility for John’s survival was left open at all indicates that it was Winston’s aim for John to live the whole time.
Why Winston Might Be Joining Forces With John
With John and Winston being long-time friends, the latter might be covertly pulling the strings to aid in John and the Bowery King’s High Table battle. Winston has previously expressed admiration for John establishing a normal life after his initial retirement. He was also able to convince John to unite against the High Table after John had been sent to kill Winston.
In seeing how much John has had to go through since his wife’s death, Winston could secretly be John’s greatest ally in trying to regain his freedom. If that is their shared goal, it makes more sense that Winston would try to cover his tracks by feigning an attempt to kill John. The guidance Winston provides in the trailer for John Wick 4 also indicates he has an instrumental role in the possible escape route that John could have. With John and Winston seemingly on the same page in John Wick: Chapter 4, they may even continue their alliance in the spin-off Ballerina (which might take John Wick 5‘s place.)