[As with the other entries thus far, this post carries heavy spoilers for the events of John Wick and John Wick: Chapter 2.]

This was originally intended to be a section in one huge post, but as I worked on it I realized that it made more sense to break the mega post into separate entries, as it dealt with four main topics—with two of those being close enough that they probably will remain grouped together. 

Much of what I have here originated in replies I made to other fans, and to content creators, on Youtube, when questions or comments were made regarding things like:

◆ Why Winston is still helping John despite the excommunication order that’s in play for the third film

◆ What the outcome of the film might be

◆ And whether this third film will hit that magic mark and create a trilogy of movies where all three entries are strong, rather than having the series fall apart with the second and/or third film. 

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As you can guess from the title here, in this post I’ll be addressing some questions and theories related to Winston and what his role might be in Parabellum.

Winston’s Role

It’s been asked why Winston still appears to be helping John quite actively in the trailers for Parabellum, given the fact that Jonathan is now excommunicado. People have also pondered what role Winston will play in the larger picture here. One particular suggestion was that Winston will use John to stage a takeover of the Underworld, becoming head of it himself, and I think this is extremely close, if not dead-on. 

As to the question of why Winston and Charon are still helping John, and also how Winston might fit into the larger storyline, here are the factors I see at play:

1. There’s still the grace period to be considered. Rather than simply jumping ahead, the third film will let us watch as John races to rally what resources and opportunities he can within the one-hour head start that began at the end of the second film. (As an aside, I absolutely love this, especially because that cliffhanger ending to Chapter Two felt like such a gut punch!)

So when we glimpse scenes where John is being aided by Winston, the Continental’s doctor, and others who would be bound by the Excommunication order, it may simply be taking place within the grace period. 

2. Winston gave John a Marker from himself at the end of the second film. Based on what we saw and were told in the second film, the rules regarding Markers are considered core and inviolable, on a similar standing to that of the rule strictly forbidding “business” on Continental grounds. So I suspect that Winston was planning ahead and making sure he’d be able to “legally” help John later on, once the head start was up. This is especially reasonable considering that there’d theoretically be little need for it if John simply planned on requesting a favor within the one-hour window. Though then again, it’s also believable that Winston would cover his bases even so, given himself extra insurance in a way that would make an attorney proud. 

3. Winston has already displayed that he has both a roguish streak and a special fondness for John, and that he’s thus willing to bend the rules for him, though he also tries to reign John in at times and calm him down. 

We see the former role demonstrated in things like how he ultimately informed John of Iosef’s location in the first film, after having initially turned the request down on the basis of rules. 

And examples of his reigning in of John can be found in how he gave John a bit of a scolding over the marker situation in the second film, as well as how he urged Jonathan to calm down and walk away during that final and fateful scene with the ironically named Santino. 

4. Along similar lines as the roguish streak, it seems that Winston refuses to be intimidated by the High Table—as seen in his interactions with Santino D’Antonio. 

Winston made sure that Santino recorded the completion of the marker, ensuring John would be properly covered, calmly and politely ignoring Santino’s protestations that it was pointless. And in that same scene he proceeded to warn and arguably scold D’Antonio over the waiting wrath he had unleashed with his actions.

And an exchange later on in the movie showcases Winston’s refusal to be either intimidated or impressed, even with Santino’s new status as member of the High Table:

Santino: Winston.

Winston: Mr. D’Antonio.Your evening has been colorful, I see. Seeking safe harbor, I presume?

Santino: I want his membership revoked. Now. 

Winston: In the eyes of this institution, Mr. Wick has breached no legalities.

Santino: Then you know that I have the right to demand of you—

Winston: Nothing. You demand nothing of me, Mr. D’Antonio. [Removes reading glasses.] This kingdom is mine and mine alone.

Santino: All right. Then enjoy your kingdom, Winston, while you still can. 

Winston: [Is replacing glasses] And you its privileges, sir.

5. I believe Winston was aware—just as Claudia, Cassian, and John himself were—that Santino’s newfound power would’ve been disastrous had he kept the position on the High Table. And I believe that he supported the general concept of what John did, just not the violation of the rules to do so—and I also believe that this concern about the rules was likely more about preserving Jonathan’s wellbeing than anything else. 

Though I will note that Winston can definitely be a stickler for the rules sometimes—as seen in his early conversation with Jonathan about respecting the marker and the necessity of rules in general.  I actually do like that about Winston, as it not only suits his overall character—he’s the epitome of the proper, formal, elegant, yet also extremely dangerous vibe that characterizes the Assassin Underworld as a whole—but also demonstrates that while he favors John, he doesn’t simply go overboard and enable the man to run rampant with no correction. In the panel interview shown in my article here, we see Ian McShane commenting on this, noting how Winston will become more stern and direct in his reproofs as Jonathan edges closer to crossing major, risky lines. 

Some people have complained about the favoritism aspect, but it doesn’t bother me and is instead something I like, because they’ve made sure to balance it out, and also as you learn about John’s place within the Underworld, it makes sense that he would be granted extra consideration. I speak about this more in my above article about the paternity theory. 

6. When we add all of the above points together, I think a picture develops that may be indicative of what Winston’s role will be in this new film. It’s pretty clear that he’s going to be a significant ally to John in this film. That was already set up at the end of the second film, and I’m definitely glad that the creative team seems intent on following through with that. 

But even more intriguingly, I suspect Winston is also angling for something major here—a power play, basically. I think that earlier theory I mentioned about taking over the Assassins Guild is at least partially right. 

John has already run afoul of them—that much is certain. But the trailers also hint at tensions between them and Winston. The Adjudicator asks why Wick is still alive, and also makes a comment that no men live above the rules. While my guess is that the latter statement may have been more in reference to John, the glimpses we see also suggest that Winston himself is now in a tense situation with the High Table due to his support and protection of Jonathan. And given what we’ve seen of Winston in the previous films, this could be the straw that breaks the camel’s back; the Wick issue might be the matter that crosses the line for the High Table and leaves them no longer willing to tolerate Winston’s own roguish streak. 

Behind-the-scenes footage from the set a while back also has me thinking that they may plan on some wider “house cleaning,” removing other rogue elements from New York. (Don’t want to give too much away, but I suspect a key, charismatic, and nostalgic character from the second film will either be assassinated or have a very narrow escape. Watch your back, boss! Or throat, as it may be….) 

But let’s say that last bit was a red herring or has been removed from the final version. Even so, I think it’s entirely plausible that we’ll reach a point where it becomes a him-or-them situation between Winston and the High Table, and even toeing the line won’t be enough to save him. 

The questions John asks in the trailers—“Are your services still off limits to me?”—may be a revealing one. Why exactly would John ask this? The question seems needless if either we’re still within the one-hour grace period or if John simply plans on invoking the marker Winston granted him previously. And why exactly would this be a possibility at all? 

Now, trailers are always  bit shaky due to how things are sometimes edited—for example, a character says a line and is replied to by another character, but in the movie we find out the two pieces of dialogue were between different characters or from separate conversations. 

But that caveat given, what we’re shown in the trailers suggests that Winston promptly provides aid to our renegade assassin, despite the rules. Between that and the question asked, my suspicion is that something’s taken place that has made Winston willing to go fully rogue the way John himself has. If the High Table has indeed decided to add Winston to its hit list, that would make perfect sense—all bets are off and the rules Winston and Charon are normally bound by and observant of no longer apply. 

And there’s an interesting kind of circularity to this, because it’s likely Winston’s support of John that has landed him in this spot in the first place. But given the vibe this character gives off—he’s intimately knowledgeable of this world and its players, holds a special and privileged position within it, and tends to weave his way through things quite calmly and gracefully—another question must be asked: Is this really so random?

Near the end of the second film, we see Winston urgently attempting to talk John down from the proverbial ledge. I do believe he was truly sincere in that. But once John made his choice, the wheels may have started turning at once. Indeed, they may already have been in place well in advance, as a contingency plan.

There’s been a theme throughout these films that the more knowledgable and experienced people, those who’ve been around a while, understand what John is really capable of—that it exceeds even the legends about him—and view the man with respect or outright fear accordingly. 

When John issues a warning to Winston in that fantastic scene at the end of the second film, the three-word reply Winston provides says it all:

John: Winston…. Tell them. Tell them all. Whoever comes, whoever it is, I’ll kill them. I’ll kill them all.

Winston: ‘Course you will.

Winston’s reply is given with not the slightest hint of sarcasm but instead with full faith and a calm smile that could be described as downright fatherly. 

His comment in the trailers about Wick versus every other assassin in New York City amounting to even odds is yet another statement of affirmation. 

And it seems to me that Winston has already chosen to lay his bets on Wick. 

It’s also struck me that the scene at the fountain in Central Park also carries another meaning or two that may be hugely significant for the film. During that scene, Winston flexes his power in multiple ways, both by choosing to delay the kill order and via a visual aid, halting the crowd of people gathered at the location. 

When Wick asks why he hasn’t already been executed by now for breaking a death-penalty rule, Winston smoothly replies, “Because I deemed it not to be.” While he can’t simply ignore the rules entirely—yet—Winston is already flexing his muscles here. And furthering that, it’s occurred to me that the visual aid may carry far more meaning than I initially realized. Winston is making a point for John and the audience here about how much power and influence he really carries. 

The sense I get is that all of those people are ones who are directly loyal to and under the authority of Winston on a personal level. This poses a tantalizing question: what role might these people have in the third film? Is it possible that Winston has been building his own individual power base over time, one that would enable him to either take a seat at the High Table, operate separately from them, or even launch an outright coup? Maybe Winston plans on revamping the Assassin Underworld, or at least the New York City segment of it.

An only somewhat joking thought occurred to me recently—that by the time John gets through, about the only assassins left will be ones who are either friendly with him or who simply have sense enough not to screw with the guy, $14 million bounty or no! But the more I consider it, the more I see a serious edge to that thought. The High Table may intend to clean house, but they’re clearly going to get much more than they bargained for…and as with the “Impossible Task,” Wick may well end up clearing a path for another individual’s rise to power. [I’ll explain that situation in my piece about the domino effect within the franchise.]

And as a final note about the park scene, there was also a still released for the third film indicating that Winston and the Bowery King—Laurence Fishburne’s character—will meet up. 

Two things the Wick films are abundant with are symbolism and visual storytelling. In most films this would probably be reaching, but I keep coming back to some of the final shots of the second film, where we see the pigeons resting on the wings of the angel statue. We know that even something as mundane as that can now carry significance; the Bowery King uses carrier pigeons to distribute intel, via what appear to be SIM cards strapped onto the birds’ legs. We also know that he keeps close and detailed tabs on the Underworld and its players. Additionally, it’s been indicated that he to at least some degree exists and functions outside of the main body of the Underworld; he’s essentially part of an underground realm of it. 

If Winston intends to make a power play, then an individual who holds personal power and resources, can provide valuable and extensive intel, and is not beholden to the High Table could make for an excellent ally in this. He’s also someone who would be under threat if the High Table is now out to remove rogue elements. John was trying to prevent this by ending Santino, but it may be that the this very situation still takes place despite his efforts, and on an even wider scale than he had anticipated.

One thing I can add is that director Chad Stahelski indicated in an interview that a plot involving Winston and the High Table is intended to serve as a secondary story thread that runs alongside John’s personal story in this film. This will be part of providing a heftier story for this third entry in the franchise. 

As as final note, I’ve spent some time in the lead-up to this film musing over the possible significance of “Parabellum” in the title. 

“Parabellum” approximately means “Prepare for war,” and is taken from the longer Latin phrase, “Si vis pacem, para bellum”—“If you want peace, prepare for war.”

[It’s also the name of several models of Luger semiautomatic pistols as well as a machine gun made by Mauser.]

What exactly does “prepare for war” mean here? Does it simply refer to John’s preparations to deal with the coming onslaught, and likely serve as a counter warning that the High Table should ready themselves for him? Maybe it refers to a larger war between the current heads of the organization and what they have deemed tone rogue elements? Maybe it stands for both. Or maybe it even means that this film will only even cover the beginning phases of a larger war, and the main event itself will not be covered—that as extreme as what we’re about to witness here is, it’s merely the opening volley? That last idea would leave the door open for another film following this one, and also John’s presumed survival of the events of this third film. 

Whatever the case, my main expectation here is that Winston, aided by John’s actions, is indeed setting up for a major power play here—whether it’s largely opportunistic or instead predesigned—and that when push comes to shove, he’s chosen to lay his bets on Jonathan, and there will likely be a deep symbiosis between the two in the course of this movie. 

So, what say you, my dear readers? What are your predictions for Management in this film? 

For an alternate—and somewhat darker—theory about how the film might end for John, I recommend checking out my earlier post here:

(Spoilers) Revelations, Theories, and Possible Spoilers about a Way Out for John Wick in Chapter 3