Disclaimer: Never been mine, never will be.
Spoilers: "In the Beginning", "All Hell Breaks Loose", "In My Time of Dying" and the pilot.
Thanks to Starrylizard for casting a quick beta eye over this. All mistakes that it still contains remain my own.
Azazel never believed it, not even for a moment.
Wearing the body of Samuel Campbell, the demon listened to his captive's claim to have travelled back in time and that he believed instantly. It was no effort for him to believe that time had been warped and Samuel's own unborn grandson sat before him, plotting Azazel's demise. The only beings even rumoured to wield power of that kind had not walked the Earth for millennia, but the demon did not waste a moment disputing the fact that the young hunter before him had come from the future.
Quite the reverse, in fact. Mary Campbell - sweet, vibrant Mary - loved John Winchester with a passion that the demon knew could be twisted to his own purpose. Their progeny would be something to behold. If this Dean Winchester was one of them, then his hate-filled recognition was the best affirmation that Azazel could possibly hope for. And if this child, who blazed with an incandescence seldom seen in human souls, would be shunned and passed over when Azazel came calling, then the other, after a mouthful of demon blood, would scorch the Earth and set the skies on fire.
It was a moment to be celebrated, not feared. And when Dean Winchester stared into Azazel's eyes and solemnly vowed that he would be the one who ended the demon's very existence, Azazel never, not for moment, considered it to be anything other than desperate bravado from a hunter with his back to wall, both literally and figuratively.
Well, perhaps for a moment, but no more than that. Despite the extraordinary fire in his soul, the boy was only human and humans often let their passions fool them into believing their abilities to be more than they were. No, there was no cause for concern. Mary and her offspring would undoubtedly play crucial roles in his endgame. And maybe Azazel would have to eventually kill her, but that wouldn't matter, not once he had her other child.
And the defiant one before him? He would remember the boy's name. That kind of insolence deserved special attention.
Ten years later, Azazel bore witness that the grandson that bore Samuel's name shone with a promise greater than any yet seen. The older one, who was indeed named Dean - he became a sheer delight to torture. The tears of a child were always to be savoured, but the sweetness of this boy's shattered silence was beyond description. Azazel never even contemplated taking the life of the older child. To end that delicious suffering would be such a waste.
The demon then watched as grief and rage drove the potential son-in-law that Samuel Campbell had once dismissed as hopelessly naïve to become the only foe that Azazel ever truly feared.
Another twenty-two years later, Sam Winchester followed in his mother's footsteps, trying to escape the hunter's life and the destiny that Azazel had planned for him by reaching out for "normal" and "safe" and "the white picket fence". Azazel bled and burned the girl who embodied young Sam's false hopes, as brutally and thoroughly as he had done for the boy's mother. Somewhat ironically, in a similar grief-stricken rage, Sam Winchester not only re-embraced, but took for his own his father's thirst for vengeance.
The other was still there. Although his brother and father drew more attention from the general ranks of demonkind, Azazel never forgot the insolent, time-displaced whelp from 1973.
In a remote woodland cabin, wearing John Winchester's body much like he had Samuel Campbell's all those years before, Azazel held his captive in unbreakable unseen bonds and stared into those same defiant eyes once again. This time, the demon's words were sharpened by the knowledge gained by watching and torturing this family for over thirty years. This time, the demon held all that Dean Winchester had left in the world in an iron grasp, ready to be crushed. This time, Azazel laid into every weakness he had ever glimpsed in the boy, but still his defiance did not break. Eventually, forced to resort to physical torture, the demon tried to shred Dean Winchester's body from within, but that only galvanized his family and they broke the demonic bonds that held them to come to his defence.
Gunshots, car wrecks, cardiac arrests and maybe a dance or two with a reaper later, Azazel was offered a deal. The demon could rid himself of the man who had discovered more about his plans and threatened them more than any human or demon could have ever dreamed possible. Not only the removal of that threat, but also the infamous Colt revolver which remained almost the only method in existence of destroying a demon, could be his. All that was required in return was to temporarily save the life of that same presumptuous child.
There was no reason to even hesitate. Dean Winchester never was and never would be a serious threat. Azazel mocked the desperate father with this certain knowledge, even as they sealed the deal. He would take both of John Winchester's sons. He would use young Samuel as he had always planned to and then, one day when he could take time to truly savour the victory, Azazel would utterly break Dean Winchester.
His first ever hint of doubt surfaced almost a year later. He had cherished Sam Winchester as his Chosen One for so long that the boy's death at the hands of another actually shook the demon's plan for the first time in decades, but that anxiety was short lived. He could never have predicted, but really had to appreciate the irony when Dean Winchester then squandered his own soul to put his most hated enemy's grand design back on track. The pleasure of gloating over the doomed John Winchester was nothing compared to this.
The Devil's Gate in Wyoming was exactly where Azazel had planned to be anyway, but the opportunity to personally send Dean Winchester screaming into the Pit of Hell was irresistible. The human upstart who had always defied Azazel's most fervent attempts to break him, who had once dared to claim that he would actually kill the demon destined to rule with a power not even Lucifer himself had dreamed of. Nothing was going to prevent Azazel from staring into that pitiful child's eyes and exhaustively listing every detail of his many failures. Dean Winchester would be made to know that he hadn't saved any of his family, that he had utterly failed each and every one of them.
He saw fear bleed into the defiance in the boy's eyes when he was told that what he had sacrificed his soul for wasn't truly his brother anymore, but the demon had barely started on the cavalcade of pain and desolation before he was physically wrenched away by another presence that should have been still drowning in the depths of Hell. By the time he had overcome the father's attack and turned to face the fallen son again, his victim was no longer pinned and helpless.
In 1973, a desperate human captive had fervently sworn that he would be the one who killed the most powerful demon since Lucifer.
Azazel never once believed it - never worried nor contemplated nor feared - not until he looked down past the barrel of Samuel Colt's infamous revolver and stared once more into the eyes of Dean Winchester, still blazing with that same enduring defiance.
A split second later, the bullet ripped through his heart.