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Dean goes to Hell after a deal he made to save Sam. Dean spends 4 months there in Earth time, which equates to 40 years in Hell. Sam also goes to Hell, but he ends up in Lucifer's Cage for 16 months in Earth time, which is about 160 years. Sam presumably endured because he did not end up torturing souls like Dean. Pain tolerance is normally defined as the level of pain where the sufferer acts to stop the pain. In Dean's case this was when he started torturing souls. Yet I am unaware of any instance where Sam accepted any kind of deal or broke in the sense that Dean did, i.e. giving in/losing will. Dean said he broke after 30 years, and Sam never broke.

What is the canonical reason for why Sam was able to endure longer than Dean in worse conditions, since they are both hunters and both experienced?

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Part of it is that Alastair was trying to break Dean. Break the seal. Lucifer didn't. He also had Michael to harass - and Michael had Lucifer to harass.

We could also get into Dean's whole inferiority complex and his belief that, deep down, he deserved it.

And maybe Chuck (aka God, as you probably know, Chuck ;) ) had a hand in breaking Dean. This was, to paraphrase, as he said so himself, a TV show for him. Dean breaking meant the show could go on.

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I know you asked this a while back, but here’s my thinking. One part is that Alastair was purposefully trying to break Dean and offering that way out to break the seal, as the other person answered. BUT with that said, I believe the main reason is that while Dean was given the option of a way out (to start torturing), Sam didn’t have that option since Lucifer’s cage was locked up tight with no way out. It was said in the other answer that Lucifer wasn’t trying to break Sam and wasn’t only focused on torturing him since he had Michael to harass and vise versa, but I don’t think that’s true. Lucifer had said later that Michael was driven insane was said to be curled in a ball "singing show tunes and touching himself.", so he focused his torture on Sam. So Sam honestly just didn’t have any other option except enduring the no doubt awful torture from Lucifer..

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