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Okay, in "The Man Behind the Curtain" season 3, we see how Ben came to be on the island. And there is one point where he runs away from home and meets long haired Richard Alpert who notices that he sees visions of his dead mother. Just like Jack has seen visions of his dead father. And Richard sees something special in him and the reason Ben is so insanely good and manipulation is because he grew up sneaking to otherville all the time, doing missions for them (like kill Alex and Danielle), and he has to make up lies to where he's been for the dharma folk until he kills them all. All in service of the island.
I am convinced that Jacob's replacement will be the person who doesn't use the island for their own gains. Widmore would go off island and he had a life there. So the others impeached him and got Ben, who sees visions and therefore was touched by Jacob. As Ben says in "The Cabin" when Locke wakes up from a dream and knows where to find the cabin, "I used to have dreams." Widmore created a life outside of the island and therefore ceased to be the candidate leader, or, the closest thing to Jacob's replacement in case he should ever die until more people show up to the island (That's why when the others saw the plane land the first thing Ben said was, Goodwin, Ethan, go to their camp, I want lists in two days) Those have to be lists for potential candidates just because Dogan seems to know who they all are when they say their names...
And is it just me, or does it seem like Widmore is now trying to "win back the favor of the gods" by coming in and helping out, or do we think he's just a bad guy?