Spoilers will be unmarked. Proceed at your own risk.
- The Marquis killing Charon to further rub salt in the wound for Winston after having the New York Continental condemned and destroyed. Winston can only stay by his friend's side in his final moments.
- Perhaps adding more salt to the wound still, Winston advised Charon to leave before The Marquis arrived, but Charon chose to stand by his friend's side out of loyalty.
- This hits even harder as Charon's actor Lance Reddick passed away shortly before the film's American release.
- Winston spends much of the rest of the movie mourning Charon. He tearfully leaves a lit candle at his gravesite, his reunion with John afterward being rather turbulent as Winston is clearly frustrated that both their actions had lead to the death of his closest ally. Much later, he discusses with John how hard the task of deciding an epitaph for his tombstone was, telling him how after much mulling, he eventually decided on "Friend".
- With John seeking refuge at the Osaka Continental after killing the Elder, Koji asks him if he had finally found peace with himself. John can only sorrowfully look on at his old friend, wordlessly communicating that all of his peace died half a year ago, with his wife and his dog.
- After their discussion Akira arrives to tell her father that The High Table representative has arrived. After Koji leaves them alone, Akira accuses John of signing everyone at the Osaka Continental death warrant's, knowing full well that by coming to them he was was bringing the wrath of the High Table with him, if her father rendered any aid. The silence afterwards is deafening, as John can't offer any rebuttal or defense to her accusation.
- Akira holding her father as he dies after being killed by Caine.
- To add this, it's obvious that Caine was truly trying to avoid this and gave Koji every chance he could to just walk away, but the old man's honor wouldn't allow it. Worst of all, Koji's death condemned Caine to become the subject of Akira's vengeance, something that he tearfully acknowledges when he tells her that he'll be waiting for her, knowing that sooner or later Akira will come after him to avenge her father's death, which indeed is implied to have happened by the time of The Stinger - right when Caine is just about to reunite with his own daughter. Either Caine ends up getting killed by Akira, or he may be forced to kill the only daughter of his late friend who died protecting her.
- Caine's entire situation in general. He's pretty much exactly like John Wick: a simple man who just wants to walk away from all the killings and enjoys a peaceful retired life, but thanks to his obligations to a member of the High Table, he gets dragged back into the deadly game and forced to confront old friends turned enemies because the High Table wanted them gone. And in the process of doing the High Table's dirty work, he ends up making a new enemy who comes after him to avenge the person that he killed. It becomes painfully clear that Caine is just as much a victim of the High Table's draconian laws and those who abuse them as John himself.
- Worse, because he was forced to do the High Table's work, Caine has to kill two men whom he considered to be very good friends, Koji and John Wick. And it's clear from the get-go that Caine doesn't want to kill either of them, even giving Koji an opportunity to walk away instead of fight him. Finally after all is said and done, Caine kneels down next to a wounded John and calls him "brother" one last time before he dies. Even if he is free to have a peaceful life with his daughter, he has to live the rest of it knowing that he killed two of his best friends so that he could earn said life. And with him being confronted by a very angry Akira, Caine may not be able to even have a peaceful life.
- The night before the duel, John goes to church to pay his respects to his late wife while he still can. There, he meets Caine, and the two proceed to have a heartfelt talk between old friends, knowing that the two will be forced to kill each other the following morning.Caine: Saying your goodbyes?
John: Saying hello.
Caine: You think your wife can hear you?
John: No.
Caine: Then why bother?
John: ...Maybe I'm wrong. - As funny as it is to see John tumbling down all these stairs, it's also quite chilling and sad to see how John got so close to the end - after a long and brutal fight - only to get sent back down to the bottom. Worse of all, with only minutes to spare before sunrise and John being exhausted after running the Gauntlet through Paris almost all night, this moment can make it feel like it's All for Nothing. If Caine hadn't shown up to help John when he did, it's very likely that John would indeed have failed to reach the duel in time and forfeited his and Winston's lives.
- In the aftermath of their duel, Caine, in pain from his wounds and already broken about clearly heavily if not mortally wounding John, limps over to thank John for helping his daughter be safe from the Marquis. He's clearly fighting back tears as he pats John on the back and calls him "brother."
- After four movies worth of being shot, stabbed, and run over, among other punishments, John has finally reached his limit, having been shot through the stomach by Caine in their duel. As he sits down on the steps of the Sacré-Cœur Basilica, he succumbs to his wounds, ultimately dying alone, but as a free man, no longer bound to the High Table, as his final thoughts linger on a cherished memory of his wife.John: Helen...
- His death is punctuated by the background track "Helen a Handbasket"
, a somber reprise of Wick's Leitmotif as the light fades from his eyes. - John's final request to Winston is to bring him home. Winston is heartbroken and on the verge of tears as he looks at John, perhaps knowing that John was going to die from his wounds before he could make it back to New York. He ultimately fulfills his request by burying John next to his wife, rather than at the burial plot for New York Continental members where Charon was buried.
- John's last words to Winston are "Will you take me home?" sounding completely exhausted and almost like a child asking a parent for help. As it sinks in for Winston what John means by this, all he can do is solemnly respond "Of course," as he tries to process that John is dying, and that he is about to lose both of his closest allies in less than a week between each other.
- His funeral afterward, with only Winston, the Bowery King and his dog in attendance. Honoring his last request, John's epitaph reads "John Wick, loving husband", mirroring Helen's "loving wife" epitaph next to his and in sheer defiance of the Marquis' insistence that John will only be remembered for being a cold-blooded killer.Winston: [In Russian] Farewell, my son.
- With the spoken Russian and the Ruska Roma tattoo, it may well be that Winston was indeed the one who found and adopted Wick.
- His death is punctuated by the background track "Helen a Handbasket"
- The roll credits are accompanied by the track I Would Die For You by In The Moment'', whose lyrics pretty much summarise John's reason to live, kill and also die, for the memory of Helen.
