|“||Rules. Without them, we'd live with the animals.||”|
Winston is the owner of the New York Continental Hotel, an establishment that functions as a neutral territory for hired killers. No business is allowed to be conducted on hotel grounds without incurring terrible penalties, which are often ordered and overseen by Winston.
Winston is the deuteragonist in the first 2 John Wick films but he serves as a major antagonist in the 2019 film John Wick: Chapter 3 – Parabellum, 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.
Winston seems to hold a high position in the underworld society and all assassins know the rules of the Continental. However, Winston's personal history, and that of the hotel, is unknown. It seems that the equipment used to place targets or tabs is of a dated time. Whether this is a stylistic choice or a means of protection has yet to be acknowledged.
The chain of Winston's network appears to be well-connected and respected by many underworld equipment providers, to the point that equipment orders can be delivered to the customers' hotel rooms.
Events of John Wick
|“||Have a drink, and relax... for now.||”|
Winston to John Wick.
When John seeks refuge at the New York Continental Hotel, he goes to the bar to search for Iosef Tarasov after the Russian criminal and his friends robbed his car and in the process killed his dog. Winston greets John as they are old friends, but tells him that such businesses aren't allowed in the hotel, so he's better off just relaxing. He, however, provides Wick the location of the trio which is the Red Circle Club.
After Ms. Perkins breaks the Continental's rules by killing an old assassin and friend to John named Harry, Winston contacts her for a meeting, interrupting her attempted ambush of John. Winston confronts the assassin and calmly tells her that her membership in the Continental has been revoked, in which his henchmen quickly execute her and walk away. He later calls John to tell him where to find Viggo Tarasov (Iosef's father).
John Wick: Chapter 2
After John's Marker is called in by Santino D'Antonio, Winston informs John that he has no choice but to perform the duty asked of him as it is one of the two rules of the Underworld. After John fulfills his obligation to D'Antonio, Winston visits him to ensure D'Antonio officially records the Marker as fulfilled.
D'Antonio eventually flees to the Continental where Winston tries to keep John from killing D'Antonio on Continental grounds. Nevertheless, John kills D'Antonio in front of a horrified Winston.
The next day, Winston meets with John at the Bethesda Fountain and uses his influence to make all of the circling assassins leave. Winston informs John that the bounty on him has been doubled by the High Table and that he is excommunicated from the Continental for killing Santino on Continental grounds.
However, Winston tells John that he will delay the announcement by one hour to give John a chance to escape. John tells Winston to warn everyone that comes after him that John will kill them. Winston acknowledges this and also provides John with a Marker from Winston in case he needs it in the future. As John departs, Winston calls in the bounty with orders for it to begin in one hour.
John Wick: Chapter 3 - Parabellum
|“||Oh, he has to die.||”|
Winston to The Adjudicator, talking about John Wick
After Wick is requested by the Elder to kill Winston to erase the bounty on his head, Winston and the High Table meet him 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 betrays Wick to keep his position as the director of the Continental resulting in Winston shooting John who falls off the hotel roof though John survives. It's implied that the shooting may have been planned between Winston and John. Winston notably aims for John's bulletproof suit and Charon comments that it is "well played" when looking over the roof afterward, as well as Winston's nonchalant demeanor while the Adjudicator seems quite concerned of John's possible survival. It is soon revealed that John barely survived the fall upon being taken to the Bowery King.
|“||I have served and been a beacon of order and stability to our industry for over 40 years.||”|
- Influence: Other than an ability to freeze all assassins nearby with the use of an old 6230 Nokia phone call, Winston has not yet demonstrated any particular close quarter or ranged combat skill to be recorded. He does appear to have a respectable amount of intellect, given he knew of the mark prior to the events in the first film. Winston is shown to wield considerable power in the underworld society and his authority is unchallengeable within the Continental's confines. When D'Antonio, a member of the High Table, demands from Winston at the hotel the revocation of John Wick's membership, Winston rebuffs him by saying, "This kingdom is mine, and mine alone." While negotiating with the Adjudicator, Winston stated that the High Table might be able to take the Continental from him, but he expressed doubt that they could keep it as loyalties to Winston went deeper than just that building. Knowing that Winston will be on his side was a enough for John to turn against High Table. Notably, the Adjudicator chose to negotiate rather than try further violence with Winston out of apprehension what could happen. He is also a skilled manipulator, able to convince John to abandon his quest to have his ex-communicado dismissed and to take up arms against the High Table, only to turn on John at the last second to demonstrate his true loyalty for the Adjudicator, convincing her to let him keep his position at the Continental.
- Expert Marksman: Winston is skilled in the use of firearms. When shooting John, he shot him several times without missing a single shot while also intentionally hitting the bulletproof material of his suit but still convinced the Adjudicator he was shooting to kill.
- Bilingualism: Winston speaks English and Italian.
- Colt Model 1903 Pocket Hammerless: Winston's sidearm is an ornate nickel .32 ACP pistol with pearl grips. He offered it to John and soon received it back in time to shoot him off the roof of the Continental.