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To execute someone who violated the Continental rules is not the normal punishment.
Think about it, in the first movie Ms. Perkins actually is a repeat offender. She attacked John, and afterwards, she killed Harry in cold blood without much of a reason. Harry sounded worried, but he did not imply that what she did was already a death sentence. Besides, Ms. Perkins was definitely "on business" and John instead was emotionally compromised and on personal revenge. Of course, when Wick kills Santino Winston has to do something as letting the thing go would make him lose credibility. Considering the situation, and the obvious friendship with John, he goes for excommunication and increase of the bounty; while he actually hope that John Wick will overcame even this... somewhat: "'course you will."
  • Jossed. John Wick 3 confirms that execution is indeed the normal punishment and Winston actually gets in huge trouble for even giving John the head start

Winston has an ulterior motive for giving John a warning and a head start before excommunicating him
Given the chaos and destruction that will result from this decision, and given Winston's other actions which all point to a preference for order and "rules", Winston must expect that either he or the order he works to maintain will somehow benefit.
  • It might be that considering how Santino was blatantly abusing the rules, Winston might figure that the whole thing might result in John cleaning up the underworld of people who take undue advantage of such rules and to perhaps reestablish why one should follow them.
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After John Wick upsets nearly the entire criminal underworld, there's only one person brave enough to take him in: Bain.
  • Alternatively the Dentist, who is hinted to have connections on a level rivaling the Continental's but is associated with a different group.
  • JOSSED. PAYDAY 2 is confirmed that it takes place before the first John Wick, and Bain already reincarnates as the President of the United States, the gang went separate ways, and Crime Net disbanded.

John Wick is going to die in John Wick: The Final Chapter
.Everything from the first movie has been building up to this point and its the only way John can actually find peace. But not before he takes the entire Continental with him.
  • Even better, this is why the creators of John Wick endorsed the Dog Wick parody trailer. John Wick: Chapter 3 will follow the events of John Wick's dog taking down the Continental to avenge his master's death.

John Wick exists in the same world as Agent 47/Hitman
The clothes, the style of the hotel, even the style of the movies all would fit in well as a story about a rival to ICA/47. It's not hard to imagine John Wick and 47 sharing a drink at a Continental Hotel somewhere.

The Bowery King is a reference to the Greek god Morpheus, which is also his real name.
Keeping with the theme of helpful black guys in New York being named after Greek mythology figures and doing John a service. John falls asleep to reach his lair, and later he sends John through a gated elevator like the original Morpheus use to send dreams through a gate. Plus,
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you know.

Every person in New York City is an assassin working for Winston.
That's why no one bats an eye when John is shooting at Cassian at Madison Square Garden and in the subway, and why everyone stops at the fountain. They just don't all attack John because they know they're outclassed.

John Wick is actually in The Matrix.
The easiest explanation to how Winston casually ordered everyone near the fountain in Central Park to stop in the ending scene, which bears a striking similarity to how Morpheus stopped the simulation while he was explaining how The Matrix works to Neo. Heck, Morpheus himself is even in the film as The Bowery King!
  • To add on to this, John is actually Neo and the film takes place after the last Matrix film. After stopping Agent Smith and making peace with the machines, the machines decided to give the dying Neo one last gift, and that is to give him the life he never had. So they put him into a new Matrix as John Wick, badass assassin, who falls in love with Helen (who is suppose to be trinity) and is suppose to live a peaceful and happy life with her. However as one last fuck you to Neo, Agent Smith (part of whom managed to survive in Neo) corrupts the simulation, turning it from Neo living happily ever after into having everything he loved (his wife, his dog, and his peaceful life) taken away from him and being forced into a endless fight for survival.
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John Wick's deceased wife was an assassin.
Much like John she retired from the field and decided to settle down. John knowing about her history as an assassin is up for debate but it really didn't matter in the long run. And since the sequel clearly established that John Wick's universe is World of Badasses then it wouldn't be completely out of the question that she used to be one.

Santino deliberately lets himself be killed on purpose.
He knew that there was no other way to stop John Wick's vengeance, even with the bounty he sets up on him. John's not gonna stop until he's dead. So he continually taunts John to his breaking point, hoping for John to kill him while they're both inside Continental, leading to John breaking the sacred rule and gets excommunicated, which will eventually lead to John being executed later. Even if John didn't die immediately, Winston still set the entire criminal underworld after his head, making sure that John can never ever have a peaceful life. In the end, Santino wins even if he gets himself killed in the process.

In the 3rd movie, John will use the marker on Winston.
The best way to call off the bounty on him? Use the marker on Winston. The entire plot of the 3rd movie is how he gets Winston to put his mark on the marker.

John's impossible task was to kill the D'Antonio patriarch.
Viggo's crime empire was greatly aided by John Wick dismantling the entire D'Antonio power base, up to and including its leader. This feat was only made possible by Santino D'Antonio selling out his father to Wick, perhaps expecting to be seated at the High Table after the killing. In exchange, John gives him a Marker for his help.

Santino's father knew that his son would try to kill him, so he willed his seat (and power) to his far more competent daughter. Gianna made peace with Viggo and John, and set out to rebuild her power base while Santino fumes in the background. This would explain why Viggo was able to take over New York's underground, and why Gianna's and Viggo's death would allow Santino to take New York back.

John and Gianna were involved at some point.
When Santino tells him to kill her, John reacts with Not So Stoic behavior we usually see from him in conjunction with his wife. He calls the job "impossible", which initially looks like he's referring to her being an important, well-guarded person, but he circumvents her protections pretty easily, implying that the difficulty isn't literal. His body language in the museum supports this-pacing, face twisting, pulling his hands through his hair. It suits the gut-punch conflict of someone being forced to kill an ex-lover much better than it does shock or intimidation. John never seems happy to destroy someone from the underworld he knows, but his expression when he finds Gianna's room is less resigned and more quietly distraught. For her part, Gianna seems more upset by the fact that it's John coming to kill her than the fact that John is coming to kill her. She also thinks nothing of stripping off in front of him, and he barely reacts(although this one could be put down to very little fazing John). There's no fear in that scene, just an almost tangible sadness weighing on both of them supplemented by bizarre intimacy. John goes beyond his typical mercy to stay with her until the end(risking discovery and death with every second), tightly holding her hand.

She may even have been the person who got him into the game, given that her family is prominent and John has yet to mention any family besides Helen. It gives perfect symmetry to his backstory-he got into this over a woman and left because of one-and fits with the For Want of a Nail feel of these movies, the awful, tantalizing feeling that this could have been completely different. It makes their single interaction all the more heartbreaking if she created the monster that ultimately ends her.

The third film will feature Cassian either teaming up with or helping out Wick.
Given that John spared Cassian's life, he will have created some underworld debt system (possibly similar to a marker), making it their duty to help out Wick in his most dire need. Also, it would be a great excuse to see them go full Back-to-Back Badasses against an army of mooks.

The third film will have an assassin that even Wick is scared of.
Wick is shown to be The Dreaded for all low-level thugs. However, many of the assassins going after his bounty seem relatively confident they can take him on, meaning that there may be other assassins out there even more terrifying than he is. With the massive bounty on his head now, some of them will be revealed, and separate themselves as someone John cannot defeat in a straight fight.

The third film will feature Rell, Clarence and Keanu.
Given the premise of Keanu is quite similar to the first film (People who lost their spouse got a pet to replace them only to lose their pets and go on a quest which leads to a lot of dead bodies at the end) wouldn't it interesting to see them in this film, even in a Cameo?

Wick actually did have a third option, though a pretty risky one.
Wick could not ignore the marker nor kill the man calling it in. But he could enlist the target's help in killing Santino. Publicly make every preparation for carrying out the job (since Ares is watching), get into Gianna's rooms, and then surrender. Have her bring in Cassian and stage a fake fight which ends with Wick being captured and interrogated and forced to divulge the identity of the man ordering the hit. Then they just hold him prisoner while Gianna disposes of her brother, and then set Wick loose. Risky for Wick though, because really would be at their mercy.

Abram Tasarov will have some involvement in the third film.
He's too much of an interesting character just to leave in one scene (in fact, he even got to be a part of a promotional piece). John could go to Abram to ask for help, noting that John allowed them a truce. Or, maybe, Abram decides to get involved on going after Wick, playing straight the very trope he pointed out at the start of the second film.
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