Have you ever seen the theories of Bill Cypher knowing of the Jail that Stan stayed in when he was younger?
Thats what it looked like in Dreamscapers. Some say that Bill knew of Stan’s time spent in jail. I am not doubting their theories at all. But I have a more obvious theory, I think. In the new Gravity Falls short that was released today called TV shorts 1, They have a channel and it has the show called Li'l Gideon’s Big House! and I believe that Bill knew of Gideon’s future arrest. This is the channel on the short:
See the resemblance? Amazing, isn’t it? The detail in the show mixed with the short films!!!