I keep thinking about this over and over, and it really seems like Ben wanted everything that has happened to happen, except for one thing, which is the death of Alex.
In season 2, after everyone finds out that Ben is not Henry Gale, Ben uses his manipulation techniques to make John lose faith in the island. I also believe that Ben turned on the dark light in the swan station to make John see the question mark symbol on the map. This way John became convinced (by Ben) to not push the button and even further more convinced after having seen the Pearl station tape with Mr. Eko. So Ben wanted John to lose faith, which in turn led to John not pushing the button, which led to Desmond having to turn the key.
When Desmond turned the key, it let the island be exposed for a brief moment to the outside world which led Penny to find the coordinates to the island. This led Charles Widmore to secretly find out the coordinates from his daughter and basically follow her boat with his own freighter to the island.
So despite all of Ben's warnings, it seems that he actually wanted the freighter to come to the island. This seems strange since it was the coming of the freighter that led to the death of Alex. But in "The Shape of Things to Come" it seems that Ben was not surprised to be in that particular hostage situation with Keamy & Alex. The only thing he seemed surprised about was the fact that Alex actually died. His bluff did not work. And he says that they changed the rules. In fact, it was Ben who put the idea in Alex's head to tell Keamy that she was Ben's daughter which led to the actual hostage situation. So Ben manipulated that into happening in the first place, he just didn't think Alex would actually be killed.
He also didn't seem surprised at all that Jacob's orders were to move the island. This makes sense since when he appeared in Africa, he knew when and where he'd be. He was expecting it.
This is all proof to the people who have been theorizing that Ben has experienced all this before, and maybe has done so many many times already.
Ben retains memory of it all, while the other people only retains bits of it, if that.
So to summarize, Ben wanted the Swan to blow up, he wanted the freighter to come, he wanted the island to move, and he wanted to be banished from it.
Hopefully we'll soon see why.
Theory by Scott Gingold
In season 2, after everyone finds out that Ben is not Henry Gale, Ben uses his manipulation techniques to make John lose faith in the island. I also believe that Ben turned on the dark light in the swan station to make John see the question mark symbol on the map. This way John became convinced (by Ben) to not push the button and even further more convinced after having seen the Pearl station tape with Mr. Eko. So Ben wanted John to lose faith, which in turn led to John not pushing the button, which led to Desmond having to turn the key.
When Desmond turned the key, it let the island be exposed for a brief moment to the outside world which led Penny to find the coordinates to the island. This led Charles Widmore to secretly find out the coordinates from his daughter and basically follow her boat with his own freighter to the island.
So despite all of Ben's warnings, it seems that he actually wanted the freighter to come to the island. This seems strange since it was the coming of the freighter that led to the death of Alex. But in "The Shape of Things to Come" it seems that Ben was not surprised to be in that particular hostage situation with Keamy & Alex. The only thing he seemed surprised about was the fact that Alex actually died. His bluff did not work. And he says that they changed the rules. In fact, it was Ben who put the idea in Alex's head to tell Keamy that she was Ben's daughter which led to the actual hostage situation. So Ben manipulated that into happening in the first place, he just didn't think Alex would actually be killed.
He also didn't seem surprised at all that Jacob's orders were to move the island. This makes sense since when he appeared in Africa, he knew when and where he'd be. He was expecting it.
This is all proof to the people who have been theorizing that Ben has experienced all this before, and maybe has done so many many times already.
Ben retains memory of it all, while the other people only retains bits of it, if that.
So to summarize, Ben wanted the Swan to blow up, he wanted the freighter to come, he wanted the island to move, and he wanted to be banished from it.
Hopefully we'll soon see why.
Theory by Scott Gingold