I wrote this after watching 4.16. John's 100 years in Hell without breaking kind of bothered me, so this is my attempt at explaining how such a thing could even remotely be possible.
The hospital room was quiet, but for the sound of rustling sheets as his charge shifted slightly on the bed. The dark bruising around his eyes was beginning to fade, and had he chosen to speak, Castiel would have heard the husky, gravelly tones that stood in testament to the fact that Dean's throat was still painfully bruised and swollen after Alastair's brutal attack. But as it was, the young man did not choose to speak, but stared ahead blankly with the eyes of a lost, tortured soul. They were the eyes of a broken man, a man with a burden so heavy he'd been crushed by it.
At times like this, the angel prayed that his Father would somehow intervene, wrap this broken child up in His loving arms and heal the wounds that a hard life on earth, and then soul-crushing decades in Hell had inflicted on the sandy-haired hunter. It was not his place to pass judgment, Castiel knew, but even his Father must agree that Dean Winchester had more than paid his dues. If the apocalypse weren't upon them, surely he would be granted rest and peace. It was so little to ask, and would be so easy to bestow. But now was not the time for peace or rest. The apocalypse was upon them. And Dean, reluctant hero that he was, was their only hope.
All the same, Castiel knew that something had to give. He'd seen the strength of men fail, buckle and break under lesser conditions, lighter burdens than the ones weighing Dean Winchester down. He'd been witness to the greatest triumphs and failures of mankind, and had been powerless to intervene for good or ill. His standing orders had always been to not interfere. He could not get too close. He was not to get involved.
Not today, Castiel thought, feeling a slight tremor at the prospect of committing an act of disobedience. He'd been charged with the care of Dean Winchester, and Uriel's betrayal had cast the shadow of doubt on the entire Heavenly chain of command in Castiel's mind. He wasn't entirely sure he could trust that the orders he's been given have come from his Father at all. After all, if the entire fate of mankind, and possibly Heaven itself, rested on the shoulders of this poor, broken man before him, then surely God would allow Castiel to do his job in providing comfort – even if it was only from one of God's soldiers to another. Was it not true that soldiers were expected, if not encouraged, to pick up a fallen brother when the enemy had brought him down, to carry him back to safety so that he could fight another day? And was Dean any less a soldier, though he was born on Earth and not in Heaven?
His mind made up, Castiel took his seat at the bedside of the stricken young hunter, taking a deep breath to prepare himself for what he had to say.
"I know you think you're not strong enough," the angel said, his gaze straight ahead at the wall in front of him. "But you have to believe me when I say that you have not disappointed anyone."
Dean did not reply, but gave a quiet huffed, mirthless laugh of disagreement.
"There's something you have to understand, Dean," Castiel said. His eyes slid from the wall in front of him, down the length of the sheet-clad young man in the bed beside him, and finally resting on his bruised, battered face.
"Your father didn't break in Hell."
"Tell me something I don't know," the young man croaked bitterly, green eyes still staring ahead and now swimming with tears.
"No," Castiel said, shaking his head. "You misunderstand me. Your father didn't break in Hell because he was already broken."
The angel watched as the liquid pools vibrated against green depths as Dean flinched, his head and gaze finally turning in his direction.
"The hell are you talkin' about?"
Castiel took a deep breath, unsure how to begin or how to fully explain.
"The demons couldn't use your father, Dean," Castiel explained. "It's true that Alastair tortured him, and made him the same offer that he made you. But your father was already broken."
Dean's incredulous, baffled look was enough to prompt the angel to continue.
"He was a broken man, Dean," Castiel said. "Your mother's death... It changed him. It left him hollow and empty. And when he traded his soul for yours, the last remnants of the fighter in him were lost."
"What are you sayin'?" Dean's bruised face was a perfect mask of confusion and dawning horror.
"Why do you think we allowed your father to remain in Hell for as long as we did, knowing what plans Lilith had, knowing that Alastair was trying to break the first seal?" Castiel watched as Dean's tortured eyes jack-rabbitted about the room as the wheels began turning.
"I know you would like to think of your father as a fierce warrior, and I would not rob you of that image for the world, Dean," Castiel went on. "But he was a broken man – so broken that torturing him achieved nothing. He was... lost."
Dean closed his eyes in anguish, forcing a few fat tears to dribble their way silently down his cheeks.
"The plans that these demons have been hatching in Hell have been in place long before the Devil's Gate was opened," Castiel continued. "Your father was their first hope, but that was quickly quashed when torturing him proved useless. That's why they tried so hard to convince you to take his place."
Dean opened his eyes and looked up at this.
"The Crossroads Demon?"
Castiel nodded, his vessel's blue eyes locking on Dean's.
"They needed to break a righteous man, Dean," he intoned, hoping that his words would sink in and strike home. "It is not often that righteous men find themselves in Hell. Most would not..." He paused, not sure how to continue without shaming his charge further. "Most righteous men don't sell their souls."
"Yeah, well, we Winchesters are a special breed of stupid," Dean whispered, sniffing past his own pain and tears.
"Azazel and his legions were counting on you trading yourself for your father, or for your brother."
"My life and soul for either of theirs?" he whispered. "No contest."
Castiel didn't know what it felt like to have a soul, but if he'd had one, he suspected it would have broken into pieces at Dean's admission. The human soul was a precious gift from his Father. It baffled him that any human could treat it with such irreverence. The very thought of it made him feel... sad?
"The legions of Hell have been working tirelessly for centuries to free Lucifer," Castiel said instead. "It has been their primary objective since my fallen brother was banished to his prison thousands of years ago. Breaking that seal – breaking you – " and here he paused for effect, making sure that those misty green eyes were still locked on his "was a mission they had no intention of failing. You had no chance, Dean. Eventually, they would have succeeded."
It didn't need to be said that they inevitably did succeed. The situation they found themselves in at this very moment was proof enough that Hell had had its way with Dean Winchester, cutting into him, tearing him apart from within his very soul, until he could stand it no more and had taken up his torturer's razor to shed blood in Hell. This righteous man – a man who had fought his entire life to keep the forces of darkness at bay, who had sacrificed his own happiness and security and safety so that others could sleep safe in their beds, never knowing of the evil that preyed upon them, never tasting that darkness, never realizing that they were indebted to him – this righteous man had given up his soul as a final, sacrificial act of love and had paid the ultimate price. Breaking him had broken the first seal, setting this whole apocalypse scenario in motion.
"Why're you tellin' me this?" Dean's broken voice asked, pulling Castiel from his thoughts.
"Because you need to know the truth," the angel said kindly, attempting at softness that did not come to him naturally. "The truth about who you really are, and who your father really was."
"Yeah?" the young man asked, a brow quirked in spite of the shattered, lost expression on his face. "And who am I?"
"A soldier," Castiel replied. "You are a soldier, Dean. A strong one. And you need to put your feelings of guilt aside so that we can win this war. Your father would have expected you to carry on, even when wounded."
"And what if I can't?" Dean snapped. "What if I'm not strong enough to pick myself up, huh? Look at me, Cas! I'm broken. I can't do it."
"Then you allow your brother to carry you out of the line of fire," Castiel replied simply, noticing the tall figure as it eased its way toward the doorframe of Dean's hospital room. He wasn't sure how long Sam Winchester had been standing there, but by the sad but determined look on the young man's face, he imagined that he had heard enough.
"Your father trained his sons well," Castiel said. "When one of you falls..."
"The other is there to pick you up," Sam said in a voice barely above a whisper. He smiled a gentle smile, his cheeks dimpling as he offered his big, broken brother a sympathetic look.
And with that, Castiel took his leave. He didn't know if his words had been enough to comfort his young charge, but they were the best he had to offer. Dean was a soldier, and even at his lowest Castiel knew Dean had the strength to soldier on, get the job done. It was practically part of his genetic make-up. It was who he was.
But he also knew that Dean couldn't do it without his brother. He hoped that the wild card that was Sam Winchester wouldn't be the undoing of all of them in the end. He could be the force that tipped the scales in their favour, giving Dean the strength he needed to carry out his mission. Or he could break them all and unleash Armageddon.
Time would tell.