User blog comment:Touchinos/“The Rupture” Discussion/@comment-85.8.105.136-20191027010719/@comment-188.118.143.28-20191028230544

According to the book  'The Essential Supernatural'  Alastair was the second demon ever created. And besides, Crowley is a notorious liar and even with the Knights of Hell, they have been said to be the firstborn of the First Fallen. So that the princes of hell are not actually the oldest of the old demons.

I personally think: Alastair was the second oldest demon ever created (reliable), but the Princes of Hell were the first demons after Lilith, in the form of the very first generation of several yellow-eyed demons. Alastair, on the other hand, was just a single demon