User blog comment:Epakrios/Plot holes/@comment-12891159-20140314213410/@comment-1509826-20140314234234

It depends on how quickly afterwards Michael threw Lucifer into the cage. Lets put it this way, it seems from the events, that before he made Lilith, Lucifer slipped into Eden, got man kind kicked out. He then made Lilith the first demon, then anticipating his imprisonment, he quickly laid down plans for more demons to be created, I.e. talking to abel, and presumable whoever Azazel and Samhain (and probably Alastair) where on earth, made a deal with them claiming them as his followers. Then Michael threw him in the cage, by this time he had already laid down his escape plans.