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?