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|“||Have a drink, and relax... for now.||„|
|~ Winston to John Wick.|
|“||Oh, he has to die.||„|
|~ Winston showing that he is not willing to spare John Wick over the Continental|
Winston is the deuteragonist of the John Wick film series, serving a minor, yet pivotal 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 a high-ranking member of the Continental, and does what he has to do to those who break its laws.
In the first film, Winston makes a short appearance 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 Winston confronts her and calmly tells her that her membership in the Continental has been revoked, in which his henchmen quickly execute her and walk away.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, first seen walking into the hotel with his personal assistant and concierge, Charon who discusses with him about John Wick's ex-communicado and whether or not the odds are at even, Winston responds by claiming "A $14,000,000 bounty on his head, every interested parties wants a piece of it, [I'd] say the odds are about even". After John's ex-communicado goes into effect and the emails are distributed, Winston simply remarks "And away we go".
Charon later contacts Winston of an Adjudicator's arrival to meet with him and discuss the situation regarding Santino D'Antonio's death by John, Winston greets her and immediately discloses the events that occurred in the hotel, the Adjudicator however disregards the events and conveys that she is here to discuss the rules that John broke in the hotel. Winston informs her that they still have D'Antonio's corpse which she requests to see, during this she observes his corpse and analyses the weapon of which he was killed with while Winston regards that he had no control over John's actions.
The Adjudicator disregards this however by deeming that he lives because Winston had deemed it as such and that when given the opportunity to kill John he allowed him to live, bringing up their prior history as friends. Winston attempts to justify his actions by claiming he had made John ex-communicado but the Adjudicator remains unmoved as Winston had given John an hour to escape, Winston rebukes her stating that John had broken the rules in "his hotel" to which the Adjudicator flaws. She states that Winston's paucity of fealty to the High Table is problematic, Winston defends himself by pointing out his service of over 4 decades to which the Adjudicator rebuffs him as he had been serving under the Table. She makes it explicit that she is here to adjudge his actions and gives him a week to get the Continental Hotel's affairs in order to which he will have to step down and his successor will be named. Winston simply comments for her to "Enjoy [your] stay at the Continental".
John who encounters the Elder, one who stands above the Table, is assigned the task to kill Winston. After a brief fight and chase with Zero and his colleagues, John reaches the hotel and requests to see Winston to which Charon agrees to. Winston who is in an exclusive room waiting for John informs him to tread carefully while he discusses John's task to kill him, Winston holds a gun to him and tells him not to make the mistake of feeling that it is a personal matter, requesting him that if he feels he must do so, then to put a bullet through his heart. Winston however tries to covertly use the situation to his advantage as he does not desire to resign from his position and attempts to persuade John to take up arms against the High Table with him as he has no intention of stepping down. He informs John to choose either to kill him or to join him, asking who he wishes to die as, the Baba Yaga (the Russian term for Boogeyman) or as a man who loved and was loved by his wife. The Adjudicator then abruptly interrupts the scene and greets John while asking of Winston's decision to step down, which he simply replies that "[I] think not" and John who refuses to kill Winston.
The Adjudicator then contacts the Administration and orders the New York Continental Hotel to be deconsecrated which is done so, The Adjudicator informs them that business may now be conducted on Continental Grounds and Winston remarks that "This haven is safe no more". John requests his privileges and access to guns to which Winston grants, Charon, John and other Continental employees arm themselves for the High Table forces while Winston takes refuge in the vault. During the skirmish, the Adjudicator contacts Winston claiming that he can not go forever to which Winston hangs up on her in a churlish manner. The Adjudicator then contacts Winston again and suggests a parlay to which Winston agrees, after John defeats Zero and his colleagues, they meet at the roof of the hotel.
Winston and the Adjudicator discuss the circumstances with the Adjudicator alleges that they can not continue forever, Winston affirms this but also ensures that while the High Table may take the hotel from him, they can not hold it as Winston's allegiances extend beyond the hotel. The Adjudicator then asks what they propose they shall do, Winston formally requests to keep his power under the table, acknowledging he overstepped his fealty and chooses to re-pledge his fealty to the High Table. A solicitous John remarks to Winston while the Adjudicator realises Winston was merely showing strength so as to retain his power and position, informing him that the High Table will accept his fealty, however she still expresses concern about John Wick and what they should do, to convince the Adjudicator of his loyalty Winston shoots John notably aiming for his bulletproof suit, off the roof. The Adjudicator then reconsecrates the hotel, Charon remarks that it was "well-played" and the Adjudicator departs but before leaving, goes to check for John's corpse in the alley-way however he has disappeared, the Adjudicator informs Winston of this who mistakenly takes it that John had died possibly feigning it but as such a suspicious Adjudicator warns him of the repercussions that could ensue from the Table and below should John survive to which Winston acknowledges and then remarks "Baba Yaga". It remains unclear if Winston had simply intended to feign John's death or if he genuinely intended to kill John.