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I have been thinking way too much about this mostrar and I have some conjecture I'd like to lay out. I have no solid theory, just some ideas I want to throw out there and see what tu guys think. So here we go.

In the Season 3 Official Companion, it states that Lilith is más powerful than Azazel. But in the show, he is called the tyrant that ruled over the demons. Were Azazel and Lilith counterparts, like king and queen? o did they have separate jurisdictions? Were their plans separate as well? Azazel's to create the ultimate human-demon hybrid and Lilith's to free Lucifer. o did they work together as equals? o was Azazel subordinate to Lilith? Was it her plan to create the psychic kids? If that's the case, why would she want Sam dead? But what real evidence do we have that she actually wanted to kill him? Ruby's word? Yes, Lilith pursued him, but how close did she ever come to actually killing him?
Jus in Bello: Dean is the one who gets shot and there's no telling if the demons would have killed them both. Remember Ruby showed up to help but Dean refused to accept it. She could have been waiting in the wings to swoop in and rescue Sam after Dean was dead. Perhaps hoping that the intense situation would trigger his powers.
No Rest for the Wicked: Lilith shoots her demon raygun thing at Sam, but we now know that that doesn't kill(Henrickson dicho he and the other hostages were tortured first, so the white light doesn't kill- maybe it stuns? o transports them?) The other thing is that Ruby got out of that Devil's Trap when no one was looking. Perhaps with the help of one of Lilith's minions? She provided an excellent host for Lilith when she needed to get close to the boys didn't she?

If Lilith was a part of the plan to create psychic kids, then she could have sent Ruby to Sam to encourage him to use his powers and to provide him with a foe(Lilith) to focus them on. Giving him motive as well as a guide. Sam would never have used his powers to fight Azazel because he knew that that was what Azazel wanted. But if Ruby tells him that Lilith vistas him as a rival and wants him dead, then he assumes the use of his powers is not something that Lilith desires and so right there one of the taboos is broken. After Dean's in Hell, the only time Lilith attacks Sam is when she throws Ruby at him- and thus his "fallen angel" is returned to him. After Ruby convinces him to use his powers, Lilith leaves him alone. We never see her make another direct strike against him, even though día por día he's gaining más power and becoming más of a threat to her. Because he's doing exactly what she wants? Feeding his demonic side, developing his skills, growing stronger and sliding deeper into darkness.

Perhaps she knows that he will kill her and is willing to make that sacrifice for the grand scheme?
Perhaps she thinks she can convince him to side with her against the angels?
o perhaps she thinks she can redirect him towards Lucifer? All of Sam's powers are geared towards defeating powerful demons. What does Lilith gain por freeing Lucifer? Sure, she gets Hell on Earth, but she also loses her authority to Lucifer. What if her plan is to free Lucifer so that he will begin the apocalypse (as apparently he's the only one who can) and then have Sam kill him? Then the demon that Sam trusts más than his own brother will do as she's been told and kill Sam. He'd never see it coming. That way Lilith gets to rule as queen perra of Hell on Earth.

In the Season 3 companion, it's pointed out how good of a deal Dean got in comparison to John. And it's mentioned on the mostrar as well. They intimate that Sam came back different, más demonic. That means he went to Hell. He was dead for a few days so he must have been down there for a few weeks right? Certainly long enough for them to do something to him. Bring out his demonic powers? Plant suggestions? Such as the suggestion that Ruby is trustworthy?

As for John, I find it a little difficult to believe that he withstood 100 years of torture without breaking. When Dean encounters the Crossroads Demon for the first time, she offers to bring John back. Even though he'd only been in Hell for a few decades at that point and obviously hadn't broken the sello yet. Why offer to release him if he hadn't proven that he couldn't break the seal? What if he did spill blood in Hell and it didn't work because he wasn't righteous enough? (the incident that comes to mind is when he kills Bill Harvelle to put him out of his misery-just an idea) So they knew that they needed another, más righteous soul so they offer to exchange John for Dean. o perhaps Azazel didn't want Lucifer freed and wasn't trying to get John to break the seal? Maybe he was never dado the option of stepping down off the rack. Unlike all the other souls that made deals (with the Crossroads Demon), John belonged to Azazel, not Lilith. The other thing is that Castiel dicho that they laid siege to Hell, trying to get Dean out before he broke the seal. They didn't do that with John? Did they know he wasn't righteous enough? o that Azazel wasn't trying to break the seal? o maybe Azazel didn't want to break the sello until Sam had started to embrace his demonic powers? Because if the plan all along was to use Sam to kill Lucifer, then they wouldn't want to free him before Sam was ready to take him down. And if Sam is the one who kills Lucifer (a being who is worshiped por some demons), then the blame doesn't fall on Lilith.

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