I'd sure like to see someone put together a timeline on MiB's long con. I think there may be evidence of it in almost every episode of the series.
Well at first I thought Ben might have been working with Smokey all along to get rid of John for Ben and get rid of Jacob for MIB. This first came to me in "The Shape of Things to Come" when Ben, after the assault by Keamey, just out of the blue says that Hurley, John and he must go to Jacob at the cabin and that he would know what to do to protect the island. Well back then you think Christian is really Jacob's intermediary. Then in Season Five's finale when Ilana says someone has taken over the cabin and burns it down and you realize that Christian was Alex who was Locke was actually the MIB because at that time we didn't know he was also smokey until season six then it changed how you viewed everything.
Then I didn't think Ben was working with him given the way MIB manipulated Ben--that wouldn't have been necessary if they were working together. Ben was just as shocked to see Locke was dead and "Locke" transform into Smokey at the statue. And since we know Ben never met Jacob how did Ben think the cabin was where to find Jacob? Was it just a ruse by Ben? I doubt Richard shared with Ben where Jacob was so did Ben just decide to lead Locke out to this this old rickety secluded shack that Horace built out in the woods for his wife(afterall he had to have known of it given he was a part of Dharma) then kill Locke but Ben didn't realize there was a force out there--MIB--who knew what Ben was up to and in "The Man Behind the Curtain" decided to put his master plan into motion with the supernatural display of creepiness for Ben and Locke. And then everything flowed from there.
Now Ben really thinks Jacob is at this cabin so he decides to go there when the island is under attack by Widmore in "The Shape of Things to Come", MIB knows John, Hurley and Ben are coming, MIB as "Christian" tells John to move the island and the rest is history. MIB as "Christian" tells John before he turns the wheel to find Eloise and tell his son hello for him--John realizes of the Oceanic Six the only "he"s are Jack, Sayid and Hurley and given the fact Christian was white Locke concluded it was Jack's dad. John tells Ben he was told to find Eloise, Ben knows Eloise from his time as an Other, Ben kills John, Eloise starts trying to locate the island via the Lamp Post. After Ben kills John, Jacob and MIB both want the Oceanic Six or most of them to come back to the island--Jacob to select a candidate to replace him, MIB to kill them all thereby allowing him to finally leave. MIB knows John's death will get Jack back to the island, Kate wanting to reunite Claire will get her to join up hence why he took Claire in the first place and left Aarion behind, Sun would want Jin. That left Sayid and Hurley and MIB didn't need to worry about them since Jacob had Ilana arrest him and Jacob personally visited Hurley in the cab after he was released from jail.
Clearly Jacob had been making numerous visits over the years to the real world. We saw in 76 with young Sawyer, 89 with young Kate, in 2005 when he approached Sayid to ask for directions allowing for Nadia to be run down and Ben to recruit Sayid to assassinate Widmore's associates. I'm not sure when the Ilana flashback with her in the hospital occurred. And we know he met with Widmore after the season four finale. I assume Widmore was the one who darted everybody since we saw similar darts used by Zoe's team in season six. Also Widmore had to have been told by Jacob to expect John Locke to arrive in Tunisia because in "The Shape of Things to Come" when Ben popped up in 2005 there were no cameras anywhere to be seen however in "The Life and Death of Jeremy Bentham" there are cameras watching the very exit point that deposits people in Tunisia. It also leads me to believe Widmore had met Jacob by then given how he was so helpful in getting John a passport, id, money and find the Six. He also was aware of the Coming War
What else made me think Ben might have been in cahoots with MIB was when he was a child in "The Man Behind the Curtain" young Ben was drawn to his mother who couldn't step into the Dharma village because of the pylons. What was he doing that for? But ultimately Ben wasn't knowingly working with MIB so I guess I was wrong with this initial assumption