I've always complimented myself on being the only creature - natural or supernatural, human or otherwise - who never, ever underestimated those denim-clad nightmares known as Dean & Sam Winchester. I was always, always careful to not commit the "One Mistake You Must Never Commit" that my enemies and allies always committed when they dealt with the Winchesters, and so I was always able to stay one step ahead of them.
That mistake is that you must never stop taking the measure of the Winchesters as you deal with them. Complacency equals death; it's as simple as that. As many, if not all, of the Winchester adversaries learned the hard way.
They say the road to hell is paved with good intentions? Well, it throngs with those that the Winchesters have killed.
I'd have to say that Azazel was the first to make this egregious mistake. He made it with John Winchester, and the result was no less lethal.
Oh, he led Daddy Winchester on quite the merry chase for twenty-two years but how soon after John Winchester figured out who & what he was dealing with was Azazel dead? A year? Less?
Can't say I particularly like those odds.
And Azazel's mistake? He wanted John Winchester in hell with such determined passion that he never looked past his first measure of "John Winchester will die to save his sons," which he parlayed into getting John in hell. If he had taken a second measure, however, Azazel might've realized "John Winchester will never stop trying to destroy me." Which perchance might've gotten him to realize, "I've just given John Winchester eternity on my home turf to figure out how to destroy me."
I know the old saying is "Keep your enemies closer" but that tends to work just the opposite when your enemy is a Winchester, doesn't it?
Azazel put John Winchester on the rack and waited for him to break.
And then waited some more.
He didn't break.
One hundred years Azazel had John Winchester right where he thought he always wanted him. But despite the torture, John Winchester used his time to not only withstand breaking, but to assess the territory and his enemy. He managed to look for - and find - cracks and chinks and weaknesses. He noticed patterns; even in the vast inferno-eternity of hell, John Winchester found patterns and reiterations of thought and movement and intentions.
He studied them. He memorized them. He analyzed them.
And he used what he learned to march out of hell.
Not run. Not walk. Not crawl.
When that gate to hell opened, only one human soul escaped. Bloody John Winchester. He stood up from his rack of torture and marched out.
And the beasts and minions and demons who had tortured him so long and so heartlessly didn't even try to stop him. No, as soon as John Winchester broke his bonds, it was all, 'Yes, Mr. Winchester. No, Mr. Winchester. Carry your bags for you, Mr. Winchester?'
And how long after John Winchester cleared that damned devil's gate was Azazel as dead as a herring?
A minute? Less?
To Be Continued