There were three moments in his life where John Winchester could remember feeling his heart shatter in his chest, devastating him beyond breath and rationality, leaving a festering hole in his torso that he knew would eat away at him until he found whatever justice he was looking for. Vengeance was a better word for it actually. In his righteous quest the words 'justice' and 'vengeance' were interchangeable.

The first time, obviously, was the moment it finally registered that his wife, his Mary, was dead. Dead, gone, ashes, and there was jack shit he could do about it. And with that revelation he assumed that his heart was dead, gone, ashes with her.

The second time he had been truly crushed beyond repair had been the first time he had seen his Dean-o covered in blood, a smoldering, headless vamp laying on the ground between the two of them. And then Dean looked up at him, a child so out of place in the dirt and grime of the forest, an alien among the overwhelming darkness and stench of burnt flesh, and the boy smiled at him. It was in that second that John became absolutely positive he had ruined his children. And he assumed his heart had become ruined with them.

The third was this moment. This moment where he stood and he was on the brink of having everything he had ever dreamed of and losing anything he had ever worked for if he reached out and grabbed it. This moment where his Sammy slouched casually in a motel chair, his lanky sixteen-year-old frame practically exuding the dark waves of evil as his piercing yellow eyes dared John to make a break for a weapon.

"I realize you might be a little conflicted right now, Johnny boy," Sam-Beast smirked sardonically, his yellow eyes rolling significantly. "I'll give you a moment to figure out what you want."

"I want you dead." John growled without hesitation.

"Oh," Sam-Beast pretended to wince, air hissing between his teeth sharply. "I'm hurt Johnny boy," he placed Sam's hand tenderly over Sam's heart, rearranging Sam's feature to a mask of mocking hurt. "And here I thought we had a good thing going for us. Y'know, I kill a whole bunch of people, and you arrive just in time to smell the smoke and pickle yourself." Yellow-Eyes quirked Sam's lips up in such an un-Sam like sneer John thought that maybe he could have justified himself with that fact alone. It wasn't Sam anymore. Those weren't Sam's soft, expressive eyes. That wasn't Sam's genuine smile.

Would Dean understand after he explained why he had even considered flaying his little brother?

For justice? For vengeance? That thing had done this to him. Had broken and burned and ruined his heart three times over, each time taking a piece of his family with it. And here he was. The only thing stopping John was the meat suit the yellow eyed bastard had strategically chosen.

Could I do it? John asked himself, heart beating faster at the very thought, sweat plastering his hair to the back of his neck. Could he kill his own son for some peace?

The obvious answer should have been a long, loud, resounding 'NO!' … but… but… it was all John had wanted, worked for, and craved with such an intense desire he felt fevered that he couldn't just not consider a short, sharp end and leave the guilt for later.

There would be guilt, regret maybe, if he could gather the strength necessary to left the blade in his pocket, of that John had no doubt in his mind.

The real question was; would it be worth it?

Oh God, he was actually legitimately considering killing his own son.

John didn't make it to the trash can before the unsubstantial contents of his stomach came violently hurling against his throat the first time, though he did make it to the shallow kitchen sink for the second and third.

"Too chicken to off your own kid?" Not-Sam inquired from the living room. "That's okay," he sighed, and John could have sworn he heard disappointment tainting the breath. "I was counting on it, actually." This smile was a little softer, but no less sadistic as Sam-Puppet knelt next to John's slumped and shuddering body. "You see, I like Sammy. Love 'im, even." He ran his tongue across his teeth, lingering on the canines and John felt like vomiting again. "In fact, I was hoping one day Sammy would come to see me as… well, as a father, almost."

John lashed out before he even knew he had moved, fist connecting with Sam-Freak's jaw hard enough he could almost feel Sam's teeth chipping. "You son of a bitch!"

Sam stumbled backwards, gangly limbs fumbling every which-way as he fought for balance. He worked his jaw. "Did breaking you baby boy's jaw make you feel better?" He cocked his head in mock curiosity, dark hair spilling over one of his shoulders. "I'm just trying to have an adult conversation here, John!" He held his hands out in exasperation, yellow eyes laughing. "Let's not bring little Sammy into this."

John held his bruised knuckled to his empty chest. "Why are you here?" He demanded, though it came out as more of a plead.

"Would you believe that I just wanted to see your smiling face?"

John glared ferociously.

"Guess not," Sam-Demon sighed heavily before a smile split his face and before John could comprehend what was happening his youngest son's hot breath was on his neck right next to his hand, yellow eyes burning into him. "I wanted to see what you would do. And you didn't disappoint, Johnny boy, I'll tell you that. I bet you'll be beating yourself up about this for years. Some days you'll wish you'd done it if you don't, some days you'll wish you didn't if you do." He breathed a laugh, hand squeezing around John's trachea with an impossible strength for what looked to be such a casual effort.

John gasped and coughed for air, face turning red.

"A bit of a catch twenty two, if you ask me." Sam-Lie continued conversationally as John clawed at his hand, leaving bloody welts is his desperation for air. "If I were you, I'd just kill him." He grinned. "Better to think about how you could have saved your boy than to look in the rearview mirror of that cherry ride outside and look at your little boy, thinking 'I shoulda killed you when I had the chance', don't you think?"

John did think. His eyes were rolling back in his head and his fighting was growing weaker, but he did think it was better to think 'coulda' instead of 'shoulda'. The urge to vomit was his again.

"Stay conscious on me, John," Sam-Monster slapped him none too lightly across the face a few times. "I can't make my point here if you're off in LaLa Land."

"P-point?" John coughed.

A twisted grin curled across Sam-Evil's lips, curving them nightmarishly. "This is how it's always going to be, John." He heaved a savoring breath. "You can't stop it. You can't stop me. And you certainly can't stop little Sammy here. It's destiny."

John started to gurgle out a counter-response, only to be interrupted by the sound of the door being unlocked.

"Hey, dad," Dean called distractedly as he backed in the door, arms full of groceries. "They were out of your—" He turned and the grocery bags tumbled to the floor.

Sam-Devil gave one last ghostly smile before tilting his head back and howling out a scream, a sulfuric cloud of black smoke erupting from his throat violently before ricocheting out of the door Dean had just opened.

Sam collapsed to the ground.

"What the hell happened?" Dean demanded, vaulting over the counter to reach his brother. "Sammy? Sammy!"

As John gasped heavily for air, the bruises of Sam's fingers already blooming across his throat he couldn't help but ask himself the same question.

Destiny had been forced down his throat, that's what happened.

John's brow hardened and he made the final resolution to screw over destiny. To work Sam harder, to make Sam stronger, to build Sam into a hunter.

Though John Winchester couldn't see it at the time, the real Catch 22 here was the more he leaned into Sam, the farther he drove him away, the less he was involved, the closer that yellow eyed bastard could get.

The fourth time his heart broke beyond repair was when he looked into his rearview mirror two years later and the back seat was empty.

The thought flashed across John's mind before he could comprehend it was even there.