Aside from its title character, the most important personality in the John Wick action
saga is Winston, proprietor of the New York branch of the Continental Hotel. His past is
shrouded in mystery, but here's what can be pieced together about it from what we've seen so far.
Winston, as of this video, has not exactly fought in the same way
John Wick and the rest of his adversaries have, but he has displayed some of his skill. He is
shown to be a pretty impeccable marksman, but probably his most obvious skill is his
capacity for leadership. He commands attention and loyalty by doing actually quite little,
because it is clear that everyone interacting with him understands who he is and where he came from,
much the same way literally everyone in the universe interacts with John Wick. It's not just
The Rules giving him clout; Winston is known like John is, but it's displayed with negative space
and narrative — it's what people don't do or say around him, up to and including The Adjudicator.
He's also an excellent negotiator, able to talk down hotheads on the verge of breaking
the Continental's rules -- with the exception of John when he decided to kill D'Antonio,
of course -- and acting as power broker for the hotel all throughout the third movie.
If The High Table is composed of organized crime elite, the ranks of Continental managers
must be as well. Rather than being the dons, shot-callers, and bosses of families, however,
it may be reasonable to assume that the managers of the various branches are the erstwhile
right hands of those at the Table. Who better to run a hotel for hired killers than the best of
those among them? It is likely the closest any of them will ever have to a retirement — and the idea
does in fact have a teeny bit of canonical support through Sofia's characterization.
We know the most about how to ascend to running a Continental through Sofia,
Halle Berry's character in John Wick: Chapter 3 - Parabellum.
"You do realize I'm management now, right? I'm not service anymore, John."
She is a former hunter, and in ascending to the manger position of the Casablanca branch of The
Continental, she gave up a significant part of her life. Despite the safety the hotels are meant to
provide, apparently Sofia either could not or simply chose not to take her daughter with her.
John then hid the girl for her, which is what created the Marker relationship between them.
Sofia is less than ecstatic about fulfilling the Marker and describes her life as Management as
the most peace she's ever had, despite the loss of her child. Perhaps Winston
was similarly motivated in seeking to run the New York Continental, and later on,
fight so hard to retain his lordship over it and remain in respected and feared status
with The High Table. He doesn't just take the job seriously, he relishes it, as he levels The Rules
against D'Antonio in John Wick 2 when he tries to have Wick's membership revoked. There's a
personal flair in how he enjoys thumbing his nose at people of theoretically-higher status than him.
In the third film, the Adjudicator gives Winston one week to get his
affairs in order before he will be replaced as manager as punishment for assisting John.
"I've been of service for over 40 years." "Under the table, serving the table. Everything is
under the table. I understand you have your loyalties but this can not be overlooked."
It's unclear if those 40 years of service is all time spent running The Continental or not.
If it is, he would have ascended to the job in his 30s, which would likely
be a prestigious thing for someone so young,
and such a long time in such a cushy job certainly could make anybody a little possessive of it.
John Wick 2 ends with John meeting Winston at the Bethesda Fountain, where Winston tells him that
the reckoning he will suffer in the next film is at hand. We see Winston make a phone call
to make John excommunicado, and he must give an identification number to certify the order:
11111. That feels like an awfully low identification number, meant to evoke the
idea that Winston has been around a long time — longer than probably several members of The High
Table and definitely longer than whoever The Elder is, since he appears to be younger than even John
Wick. Time means history, and history begets secrets, so Winston must have a lot of them.
We can't be really sure how long this underworld system has operated.
The only clue we have to the organization's age is the displayed gold coin in Berrada's compound.
He doesn't say how old it is, only that it was extraordinarily difficult to track down.
Considering the sheer amount of people registered in the system of this universe, however,
only five digits in an ID number — and all ones, at that — means he could be somewhere
close to the foundational infrastructure of the underworld as we understand it in the movies.
Winston can pretty much have a claim to a catchphrase when he says that the rules
are what separate us from the animals multiple times across all three films.
"Exactly. Rules. Without them we live with the animals."
Is that the voice of experience? Does he remember a time before The Rules? He also
tells The Adjudicator that his loyalties "extend far beyond" The Continental,
possibly beyond the jurisdiction of The Table itself.
The biggest question for Winston's background is where the friendly relationship with John begins,
and now possibly ends. It's frequently stated and even occasionally leveraged
against Winston that he is pretty fond of John, but understanding why is a game
of speculative leaps of logic. They don't appear to have much in common,
since John's rather a hothead and Winston is savage in his calm, icy attitudes towards others.
"Have a drink, and relax...for now."
Winston gave John a Marker at the end of John Wick 2 – a Marker that has yet to be identified
or cashed in — as well as the hour head start to get away. Winston appears to owe John a favor,
and the stakes have not gotten high enough yet for John to feel like cashing it in.
Winston knows John well enough to hold his sense of internal honor and emotional state against him,
as he does when asking which "version" of John he wants to die before confronting The Adjudicator.
"Who do you wish to die as? The Baba Yaga? The last thing many men ever see? Or as a man?"
We don't know if the result, which puts John over a balcony to fall four stories,
is a double, triple, or even quadruple-cross, but it nonetheless proves a level of intimacy
between the two men. In any other context, you wouldn't hesitate to call them friends.
Winston displayed total willingness to break rules for John up until he was forced to
declare him excommunicado. In this universe, that comes from trust earned off the back of
taking risks for each other. The tale waiting to be told between them will likely be part of the
plot for both the fourth and fifth movies in the franchise. Is it a display of the
ultimate trust to undermine The Table, or an ultimate betrayal to leave John to the wolves?
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