|“||Rules. Without them, we'd live with the animals.||”|
Winston is the owner of the Continental Hotel, an establishment that functions as 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 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
During his search for Viggo Tarasof and his friends, John seeks refuge at the New York Continental where he converses with Winston. Winston provides him the location of the trio which is the Red Circle Club.
After Ms. Perkins breaks the Continental's rules by killing someone on the property, Winston contacts her for a meeting, interrupting her attempted ambush of John. For her actions, Winston has Perkins executed and then, disgusted with Viggo Tarasov's actions, calls John to tell him where to find Tarasov.
Events of 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.
Events of John Wick: Chapter 3
After Wick is requested by the Elder to kill Winston to erase the bounty on his head, Winston betrays Wick to keep his position as the director 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 aimed for John's bulletproof suit and Charon commented that it was "well played" when looking over the roof afterwards, as well as Winston's nonchalant demeanor while The Adjudicator seemed quite concerned of John's possible survival.
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 Adjucator, 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. Notably, the Adjucator chose to negotiate rather than try further violence with Winston.
He is also a skilled manipulator, able to convince John to abandon his quest to have his excommunication 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 Adjucator, convincing her to let him keep his position at the Continental.