And rather than explain why I think it's a possibility, I'm just going to post a link to an article I wrote about Azazel & Lilith
link

i truly believe there's a connection...but i just can't figure it out yet..

Yeah- I feel that way too, lucy! I just can't quite nail it down.

Sheesh! What an amazing article; you present so many plausible ideas! I'm really surprised that the Season 3 O.C. says that Lilith is more powerful than Azazel. Sam has the powers of a yellow-eyed demon, and he was able to stop Lilith in NRFTW. Personally, I would not assume that she used the white light to torture Henricksen and the others, and I do think her intention was to kill Sam. She seemed very surprised when he was able to stop her, and she took off pretty quickly.

My gut feeling is that Azazel and Lilith were not working together. Azazel was all about war, weapons and the glory of him or someone else leading the hordes from Hell. It seems Lilith would rather skip the middle men and go right to the top. And then there's Ruby. It wouldn't surprise me at all if she were actually Azazel's daughter ("Meg") and is fulfilling her father's plan. We've never really seen any spectacular powers from Ruby except for her knife. Despite Az having yellow eyes, "Meg" was a black-eyed-demon, therefore among the least powerful. I still find it strange that Lilith would send Ruby back for one last chance to kill Sam, after sending her "far, far away". "Meg" could have come back claiming she was Ruby, because she may have discovered that Sam already trusted the former Ruby. And we still don't know what Azazel's end game is.

Lilith somehow knew about Sam, and if she was working against Az, she would have delighted in killing his "pet project", but once she saw that Sam was already able to repel her white light, she decided instead to break the seals that would release Lucifer. Maybe she considered Az her only real adversary, and if she stopped Sam, then she would thwart his plan. I can't figure out what her ultimate goal is either, but some lore states that she is the wife of Lucifer - interesting, but who knows?

I know 67impala! I was surprised that Lilith was listed as more powerful too- I'd always thought Azazel was. We've seen two white eyed demons (Lilith and Alastair) but only one yellow eyed one. Weird.
Interesting theory about Meg coming back disguised as Ruby! Hmmm. There's just so many questions. We really don't know what Ruby/Meg's plan/motives are, or Azazel's or Lilith's. I can't wait to find out!

and btw, I LOVE the icon of Azazel! :D

Well...Official Companion or not, they could have made a mistake...I can't wait to find out either, the possibilities are so exciting!

when you guys come out with all of this it makes me feel so lazy...!

I feel like they have communicated with each other some how....I mean doesn't everyone in hell keep contact...maybe I am getting it confused with school!

My gut says that there is no connection between them but I'm not sure.Concerning the possibility of a Ruby/Meg disguise, it would be very interesting if it happened on the show but I think that it isn't true because we've seen Ruby confront other demons (eg Malleus Maleficarum) and they didn't refer to her as Meg or even hint anything.I might be wrong....who knows?We'll have to wait and see.