There was no right answer. An admission that John had lasted longer than Dean had would hurt his son, he knew it, because it would be a comparison made for a failure, as there was no fairness of fractions and math here. There was only 'he lasted longer than me'. An admission he'd lasted less than Dean had would, John thought, make him less in his son's eyes, even if they did know the worst of Hell. Any admission short of lasting nearly the whole time would mean revealing that he'd tortured people for decades longer than Dean had, admitting how much of a monster he'd become.
There was only the truth. And the truth was something John didn't want to admit, because it was an admission that meant hurting Dean, given what he knew from the Ethros demon picking around in his head, and one that he stood to lose so much in terms of the way his sons had looked up to him all their lives.
But it was a truth he had to admit, had to say it, so he and Dean could work through this together. He had to be honest, but honesty had never been so goddamned hard as it was now.
"Barely thirty-five years." John Winchester, the man rumored among hunters to be the toughest, most relentless sonofabitch there was when it came to what he was after, the man who'd hunted and destroyed a nearly legendary amount of supernatural things, depending on who you talked to, and he hadn't even lasted half his time in Hell. In life, he'd survived the worst thrown at him for over twenty years, but in Hell, he hadn't kept refusing.
Of course, in Hell, there was no thought for reprieve other than the reprieve offered at the end of each day. There was no thought that if he lasted long enough, God would see his plight and save him because he'd made a deal, not been a monster. He'd known, every day, that there would never be an afterlife with his wife or his sons, and that knowledge had eventually broken him right along with the torture. He would never see them again, and even knowing he'd saved his son hadn't saved John Winchester from the way Hell broke everyone in the end.
"By the end of some days, I couldn't even remember my own name anymore because of the pain. They had John Winchester in Hell, they all wanted a piece of me, came up with new ways rip me apart because of who I was – and they'd tell me who I was when I couldn't think of anything but the pain."
He wanted to stop, but in speaking there was this tiny sliver of relief, that someone at least knew the truth, that he'd have at least one more person he didn't have to flawlessly fool that everything was okay. "I'd refused over and over but every refusal tore another part away from me, so that on every new day, there was still all of me physically, but less and less of me in every other way. And one day, I just couldn't do it anymore," he said, the pain, the emotion, choking him as he wiped at his face. "So I tortured those souls, whether they'd been monsters or good people who'd made bad deals, and I did it every day for almost sixty-five years."
He fell silent a short time, covering the silence by draining the beer in his hand and getting another out. What he intended to tell now was selfishly for himself, a desperate man's attempt to negate those sixty-five years with some small show of not being wholly a monster – but it was a drowning man's delusion, because he still felt every inch the monster.
"Refused once. Nearly thirty years of torturing others and one day I just refused. They put me back on the rack and made me regret even second of that thirty seconds of refusal, over and over until they broke me again and I went right back to that torture all over again."
He dropped his head, eyes closed. "When you give in, you do it to survive. It's animal instinct. Hurt or be hurt. They leave you nothing but that instinct. I watched them cave the first day, them last barely a year, because a soul's not meant to endure that for decades and decades."