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Apologies for the block of spoiler text:

Throughout season three:

Lilith holds the contract on Dean's life, she does this so that they can break him in Hell, and open the first seal on Lucifer's cage

Normally a Cross Road's demon holds the contracts on a soul, as they are the ones who the brother's have manipulated to get them back.

Now, I'm sure someone will come along and say

"But it's Lilith!, she can do what she wants! You try and tell her she can't do that, to those pearly white eyes!"

But by their own admission demon's play by the rules. I guess then I'm asking, did Lilith/The Cross Roads demon play by the rules with his contract? Or did they bypass them some how?

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    Purely speculating here, but Hell is depicted as being very hierarchical - every demon answers to somebody else. The regular Crossroads demons answer to the head Crossroads demon, who in turn would answer to a higher-ranked demon - they either answer directly to Lilith, or she's a few ranks above them. Just because higher-ranked demons don't normally get involved with or take an interest in Crossroads deals, it doesn't mean they can't in rare cases (Dean would no doubt be one of those). – Anthony Grist Oct 14 '12 at 13:15
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At that time, Lilith held all the contracts. She had Crowley as her right hand man, who managed most of the contracts. The Crossroads Demons we saw were merely the lowest-ranking demons in the organization, and were empowered to create contracts. When Lilith was killed, Crowley took over as leader of the Crossroads Demons (amongst other things), and so he now holds all the contracts. Lilith specifically held Dean's contract, due to her personal interest in his case. Both Lilith and Crowley have shown the authority to break contracts, which suggests they are also the ones who can hold them.

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