Sometimes I wonder if the demons slowed down time specifically for Dean. Like, if they knew they needed him to say yes so they made each month feel like 10 years. Maybe John really was only in hell for 8 months. Maybe Sam was only there for a year. But Dean feels like a failure because he assumes each month felt like a decade for them and neither of them cracked the way he did.
I mean, could be. The other parts of Hell that we’ve seen (specifically Sam’s trip to find Bobby in 8.19, and even their little meeting in 11.09 and the trip to the Limbo Cage in 11.10) have shown no indication that Hell Time overall runs any different from “earth time.” But you’re right on that count– we really don’t know if all of Hell runs on one set time, or maybe different parts of Hell run on different schedules, or even if some of the more powerful demons (like maybe Alistair…) are able to manipulate time or the perception of time to their needs.
For some reason I’m now specifically thinking of this part of Hell and feeling a twinge of agony just imagining it:
(screencap from this post)
I guess in a line that long there’s no reason to make time seem any more drawn out. Probably saves energy to not have to mess with time itself and just create excruciating boredom through natural means…
But on that note, I can’t imagine that the time dilation wasn’t something that Lucifer would’ve been able to control in the cage either. We just never heard from Sam what his perception of his time in Hell was. It was horrifying enough to know he was there in the cage at all, you know?
Nor do we know what John’s perception of time was. And you’re right– ever since Alistair used the fact that John never broke to torment Dean in 4.16, I’ve wondered about how easily John managed to escape when the Devil’s Gate was opened in 2.22. I mean, I wondered that at the time I first saw 2.22, but didn’t have the context of Dean’s experiences on the rack in Alistair’s care, nor the fact that John had supposedly been receiving the same sort of hospitality that Dean had, tied to the rack and tortured every day and never breaking (supposedly). If that had been the case, then how did John escape through the Devil’s Gate in 2.22?
So yeah, I’ve always tried to find a headcanon that sort of covered all of this, but I’ll give you the fact that “time being malleable rather than fixed” does lend some support to the theory that John’s experience in Hell was in no way similar to Dean’s.
It’s all technically retcon-y anyway, from the point of much later canon (like 4.22 that shows us how Azazel got his orders from Lucifer to find Lilith, and take instructions from her on how to free him from the cage… which started with the “special children” and ended with the opening of the Devil’s Gate to free Lilith specifically… because that’s when she showed up in canon as the “new leader rising in the west,” to quote Tammi the demon in 3.09). Since the apocalypse arc hadn’t been in the plans back when the Special Children and YED were the Big Story of s2, they salvaged what they could and sorta handwaved the rest, leaving us these big ??? moments to fill in for ourselves. Not really fanfiction gaps, but at the very least headcanon gaps. :P
Which leaves us with Dean’s experience of 40 years of torture over four months of Earth time combined with Alistair’s taunting line in 4.16, that he’d had John on the rack and he never broke. Which makes the fact that John not only walked out through the Devil’s Gate in 2.22, but that his soul was intact enough for him to float up to heaven after helping to kill Azazel… How much was he honestly tortured, and for how long?
It took an army of angels to free Dean from Alistair’s tender care, how the heckeroo did John not only stroll out the door, but more urgently how was he not mostly demonized by the experience? He looked pretty… not-horrifically-tortured for near-on a century, you know? (x)
It’s interesting though, because we do know that LILITH had her own agenda after 2.22, to send her mole Ruby to infiltrate the Winchesters’ trust and begin readying Sam to break the final seal. (which again was not the plan at the time 2.22 aired– the original plan was for Sam to save Dean from his deal, but then s3 was cut short by six episodes by the Writer’s Strike and they didn’t have enough time to make that happen, so they went with plan B and sent Dean to Hell anyway… yadda yadda enter the Angels… so we get to find fun theories to explain away Real World Production Issues with wild headcanon. I actually love doing this… just a stroll through my bucklemming canon acrobatics tag is proof of that.)
So we know Azazel was the one who Lucifer tasked with setting up all the pieces and eventually freeing Lilith, but what if Lilith (or even Lucifer) needed Azazel to die after that point? He’d fulfilled his role, and just like Lilith needed to die to complete her role in 4.22, what if Azazel needed to die to complete his in 2.22?
Lilith and Alistair both had those creepy white eyes. What if they were in cahoots with regard to making sure John Winchester was ready and waiting to walk out that Devil’s Gate when Lilith made her escape, knowing that he would be key in helping make sure Dean killed Azazel? Then with Azazel dead, John’s debt to hell fulfilled, he was able to just boop off to heaven in a burst of white light, no demonic damage to his soul at all… Kinda seems weird given what Dean related about his own personal experiences in Hell…
But gosh wouldn’t that suggestion in 4.16 hurt Dean, to think of what he himself became during his relatively short time in hell compared to what John endured and was still able to waltz off to heaven afterward with no stain on his soul. Probably went a long way toward making Dean feel like a failure. Again.
So, yeah, I totally buy the “Hell Time is flexible and not fixed exclusively to Dean’s description of his own experience there.”
Because it doesn’t line up with any other glimpse of Hell we’ve ever had.
Well, this went through some detours to get to the point. :P