Disclaimer: Wait, you mean they DON'T belong to me…awww man, stupid dreamland…*sniffle* Well that Eric Kripke sure is lucky!
Spoilers for season 2, episode 11 and season 4. (Few different episodes in season 4)
Breaking Point
He was in Hell for 60 years, enduring the torture. His time was up too soon, all because a man had shot him in this crazy town while they packed to leave. Leaving Sam sooner than expected, with no way to find a get out. He knew he was barely holding on each time he was made the offer, but he kept tough.
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Then, he's back to the Wednesday he died. Time restarting and the 60 years of Hell are erased, they practically never happened.
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When his deal is officially due and no way out is found, this time it's real.
No redo will work, no more time loop, though he doesn't really remember the 60 years anyhow.
But Hell remembers, they remember the one that never broke, that got away. During those 60 years they tried to break him, but now they are more determined to break him. They deploy all tactics, use everything they have.
What about Sam, the reason you're here…what if we took him anyways.
If you accept, there is no more pain, and when Sam, who is so close to losing it and joining us, enters Hell, you can be the torturer. Then he can be showed mercy where no one else will.
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So after the constant mantra of chants and 30 years of holding on (plus the other subconscious 60 years), he breaks. He learns the right methods in the most gruesome and painful techniques. He doesn't realize they needed him to break, needed that seal to break, that they need him to stay in Hell.
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Once more he eludes Hell when he is raised by an Angel.
This time the memories remain, and he only remembers the second time in Hell, the taunts, torture, offers and the fact that he broke.
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Please let me know what you thought and thank you for reading.
Chow, Siara