Per wiki policy, Spoilers Off applies here and all spoilers are unmarked. You Have Been Warned.
John Wick's death was forged and the High Table had him hidden away or even unofficially Kicked Upstairs in a positive manner.
Perhaps also in appreciation for eliminating the Marquis de Gramont, John was rushed to a secret site to recover from his injuries and given a "home" at an undisclosed location. Hence why Winston and The Bowery King don't seem all that concerned at the end of the film. John may have gotten a job at one of the High Table's offices where they give nice cushy jobs to retired people so they stay out of trouble and had all his hair shaved to help him assume a new identity. John's death was faked to keep him completely off the High Table's radar.
This is why Winston seems to blasé when asked if he's in "heaven" or "hell" because John is back where he started at in the beginning...now completely free of the High Table...but also still alive and separated from his wife.Of course, there's nothing to say he can't cross paths with the High Table in the future... Alternatively, if John didn't survive, he ends up fighting armies of the underworld in the Painkiller universe.
So, is John in Heaven or Hell? Maybe the answer is both! John is in a Karmic Reform Hell of sorts and has his own set of weapons that are inspired by his life and personality. In this setting, John gets to truly be the one you send to kill the boogeyman(s).- If he has a Stake Gun, it could fire some style of giant pencil, naturally. John may react to finding this gun with a sense of You Have GOT to Be Kidding Me!
- In a nod to the Dragon's Breath shells, John's shotgun may have a flamethrower Secondary Fire instead of a freeze shot.
John remains dead in the fifth film, which will serve as an epilogue wrapping up the story's loose ends
The High Tables handing of John Wick ultimately destroys their true "power" over the world they claim ownership of
- John was well liked and actually Fair, his shoddy treatment highlights that their cruel and corrupt (probably one example among hundreds, and only that few because they don't deal with 'small fry')
- They count on fear and/or loyalty to keep them in power, but... fear can be as slippery as a greased pig & there's little reason for the majority of their 'world' to be actually loyal to them.
- About the fear, their counting on assassins -*assassins* to not be A) pissed and with nothing to lose and/or B) vengeful after the High Table burnt their lives to the ground over a petty power play? Really!?
- They just wronged so, so many mid-level players who are going to carry a grudge, they have pull & their status has a more substantial legitimacy than 'spooky, mysterious, but distant rulers' who've proved time and again to be unjust.
- John couldn't kill the High Table, not with a gun or knife. But there's a very real possibility their own mistreatment of him was a catalyst for delegtimizing them in the long run.
- Their kind of power is only real until people stop believing in it. And they can try to fight that with their personal enforcers, but well... whether they go out with a whimper or in a bloody war to reestablish their crumbling "authority" doesn't matter.
- John died, that doesn't mean he "lost" in the end. Only time will tell of the shockwaves he caused will be enough to catalyze distate for the High Table into their ultimate downfall.
- To put it another way: famed Dictator Muammar Gaddafi was unseated after decades because a low level government official (in the neighboring country no less) confiscated some poor guys main primary means to support his family. The power of dictators can vanish like a dream, without warning. And John was one hell of a Canary in the Coalmine.
