It goes without saying, but there are SPOILERS for John Wick: Chapter 3 - Parabellum ahead!
Following immediately after the events of John Wick: Chapter 2, John Wick: Chapter 3 - Parabellum saw Keanu Reeves’ character without access to nearly all of his underworld resources and on the run from assassins after the $14 million bounty on his head. John had few opportunities to catch his breath during the movie, and as per usual, whether he was in New York or Morocco, he left a trail of bodies in his wake. He even chopped off his ring finger to prove his commitment to The Elder, although that didn’t last long.
But arguably the biggest shock in John Wick: Chapter 3 was after the shootout at the New York Continental had concluded and manager Winston, played by Ian McShane, offered penance to The High Table. In order to stay in the organization’s good graces, Winston shot John until he fell off the roof of The Continental. Luckily for John, he was retrieved by The Tick Tock Man and delivered to The Bowery King underground, and both of them are pretty “pissed off” at The High Table now.
This laid the groundwork for what’s to come in 2021’s John Wick: Chapter 4, but one thing isn’t fully resolved when John Wick: Chapter 3 - Parabellum ends is Winston’s true allegiances. Did he really screw over John or did he merely pretend to in order to secure John’s safety? That’s what we’re here to hash out.
Did Winston Truly Betray John Wick?
The world of John Wick is a dangerous place, and only the toughest and most ruthless end up on top. Clearly Winston fits that criteria and has done well for himself if he’s mangling the New York branch of The Continental.
It’s highly unlikely that The High Table would give that job to just anyone, and Winston mentions he’s been of loyal service for over 40 years. Clearly looking after this “kingdom,” as he refers to it to Santino D’Antonio in John Wick: Chapter 2, means a lot to him.
Winston has been John Wick’s most frequent ally since the first movie, whether it’s by offering simple guidance, passing along important information or even labeling John as excommunicado rather than having him executed. However, regarding that latter one and the following battle at the Continental, Winston declared that this had all been a show of strength, indicating that he wasn’t so much interested in helping John, but wanted to show The High Table he’s still not to be trifled with.
Even if Winston is more fond of John Wick than most people in this colorful underworld, he might not be willing to risk this friendship if it means losing The Continental. So when it came down to choosing one or the other, he chose keeping control of his hotel, and that meant John had to go. And even though Winston, Charon and The Adjudicator know that John’s body is now gone, with The High Table backing him, Winston should have plenty of backup if/when John comes back to his doorstep.
Now for the alternative theory.
Did Winston Actually Help John Wick?
We’ve already been over how Winston is fond of John Wick, so there’s no need to explore that again as evidence that he didn’t truly want John to die. Fortunately, there are a few other tidbits of information that support this idea.
For one thing, Winston could easily eliminated John by shooting him in the head, but instead he shot him several times where he was protected by his bulletproof suit. Of course, then John fell off a building, and in the real world, all that would result in immediate death. But this is John Wick we’re talking about; the man can survive anything that would put any mere mortal down for good.
Let’s also not forget that after John Wick fell off the roof, Charon looked down and uttered “Well played.” He could be referring to how Winston suddenly betrayed John to cover his ass, or he might have been referring to how Winston cleverly (and violently) got John out of that messiness.
Plus, when The Adjudicator came back into The Continental to inform Winston that John’s body was missing, Winston was remarkably unfazed. With how well he knows John, if Winston had truly betrayed John, you’d think he’d at least a little visibly worried about him showing back up to exact vengeance.
Finally, one of the first official John Wick: Chapter 3 - Parabellum pictures that was released showed Winston and The Bowery King together atop the latter’s roof, as seen above. Those two never shared screen time in the movie, so clearly this was part of a cut scene.
Considering that both Winston and The Bowery King were both being targeted by The High Table for helping John in Chapter 2, it’s plausible that before Bowery King was cut up, he and Winston met and formulated a plan to get John out of trouble when the time came that The High Table wanted him gone once and for all, hence why Tick Tock Man was on site to retrieve John after he fell of the building.
The ending of John Wick: Chapter 3 - Parabellum is reminiscent of the Thor: Ragnarok scene when Loki passes by the Tesseract in the Asgardian vault on his way to retrieve the Crown of Surtur. We didn’t see the God of Mischief take the cube-encased Space Stone, but we logically assumed that he did, and sure enough, it was confirmed at the beginning of Avengers: Infinity War he had snatched it. I suspect we’re dealing with a similar situation regarding Winston and what he did to John.
Going off the evidence available so far, it appears more likely that Winston was trying to help John rather than betray him, but because they were being closely watched, he couldn’t clue John in on what was going to happen. As things stand now, John is under the impression that Winston is no longer on his side, and since he’s pretty angry, you can easily imagine him coming for Winston’s head when the opportunity arises.
Given The Bowery King’s his flair for theatricality, you can bet this is a man who thrives on drama. But hopefully, if Bowery King and Winston are in cahoots, he’ll table that love and form John about this secret alliance as soon as possible.
That said, even though Winston has, at least on the surface, buried the hatchet with The High Table, you can bet those crime lords will still be watching him closely. So when the time comes that John, Bowery King and their allies finally wage open war against The High Table, it’ll be incredibly difficult, if not just impossible, for Winston to assist them.
It’s also worth mentioning that whether Winston really screwed over John or not, it might not matter either way. At the end of John Wick: Chapter 2, Winston gave John a marker for “down the road,” and along with not conducting business on Continental grounds (unless it’s been deconsecrated), the other main rule among these criminals is that a Marker must always be honored.
Winston may find himself in a position in Chapter 4 where he and John are face to face with each other again, and John gives the Marker back to him, meaning that no matter what, Winston will have to go along with whatever John asks of him or face the consequences. Fortunately, if Winston is still on John’s side, he’ll almost certainly be willing to fulfill this request purely out of respect.
We’ll find out for sure what’s going on when John Wick: Chapter 4 is released in theaters on May 21, 2021. For now, find out what’s arriving in theaters later this year with our 2019 release schedule.