Board Thread:Character Discussion/@comment-24376757-20150821192304/@comment-25926288-20150821193546

Well, to start off, Rumple isn't omniscient. Secondly, the writers said he lost the ability to see the future (somewhere around season 2-3).

Now, Rumple didn't plan any of what occured, he just got lucky. Isaac said that the story will end with Emma going dark and he did indeed tell the truth as the story "Heroes and Villains" ended and Emma became the dark One. So, it's not much of Rumple's doing, but Rumple trying to exploit things that will occur. He failed at that.