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.
After his car is stolen and his dog is killed, John seeks refuge at the New York Continental where he converses with Winston. 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.
After John's Marker is called in by 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 in a public place and uses his influence to make all of the circling assassins leave. Winston informs John that the bounty on him has been doubled and that he is excommunicated from the Continental for his actions. 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.
Other than an ability to freeze all assassins nearby with a 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."
Notes and TriviaEdit
- Both the first and second film example his near fatherly concern for John, this could be for believing John to be doing only what's right even if it meant that he defiled the first rule of the sanctuary, as he knew Santino had the order on John's head to shut loose ends, as well as after severing all ties to the marked individual by stamping his own thumb next to John's
- There is speculation that the Mark he hands John at the end of the film's sequel is a new one, sealing him an obligation to John, the reason for this is that there was no real reason to hand John the Mark and that John seemed confused without having looked at it's contents.
- Should the speculation of Winston's blood prove true, this could mean John's override to being excommunicado at the cost of having to deal with another return to his previous life.