Literal Hell
Hell wasn't fire. Hell wasn't eternal cold. Hell wasn't screaming in pain or dying over and over again. No, those things were releases, those things were sweet blessed heaven compared to what he lived in.
No. Hell was about inaction. Hell was about watching the slow destruction of everything you tried to protect, everything you tried to love. Hell was standing in this quiet room with the window to the world when all you could see was the pain and raw suffering of your children played out forever. Hell was standing there unable to do anything but watch and die a little with them inside.
"For all I know Dad died thinking I hated him." No Sam, God no Sammy. "So you're right. What I'm doing now, is too little, too late"
Sometimes he would sit with his back to the window, facing the dark wall and pretend that this was all a trick. Some brutal punishment for his sins maybe. That what was befalling his kids wasn't really happening to them. That they were happy and together and working things out so well on their own. Well, he'd always been pretty good at denial. Why should death change that?
"You can't just fill up that hole with whoever you want! It's an insult to his memory."
He flinched at the strike that Dean landed then so perfectly below Sam's temple and above Sam's jaw. The placement of it almost down to a science. It didn't help at all. His analysis that Dean had managed to hit Sam in the best possible place on his face didn't seem to help the agony that tore at him. He'd still hit him. He'd still felt enough blind rage and pain that he was losing himself. A year ago there wouldn't have been anything Sam could have said to make Dean hit him like that. Now, a mention of harming their father's memory had Dean swinging. Oh my boy, what have I done to you?
He would never have asked the question if he knew that in a few days, it would be answered by Dean as he sat on the hood of his car.
"So tell me, what could you possible say to make that all right?" As Dean's voice broke, his father started screaming. He was screaming so hard and so loud he was sure that his sons had to be able to hear him. They had to be able to see that it wasn't Dean's fault. That Dean deserved his chance at life. He pounded his fist into the black walls, he kicked at the glass window, he screamed and he cried and he roared and he raged and none of it mattered at all. Dean and Sam drove on, death in their wake, pain and despair in their future.
John Winchester figured that most people thought of hell in literal terms. Every minute of every hour of every day in this place, John prayed for the literal hell of people's thoughts to claim him. And every moment, his prayers were denied.