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I dont really know how to word this right but here it goes.
Young Ben was lured out to Richard etc. when he saw his dead mother outside sonar fence at barracks. If we assume this dead mother was actually the man in black (its what he does afterall) then it was his plan to get ben with richard and them. We already know both jacob and man in black have got things planned well in advance. This is possible a reason that jacob did not talk to ben and before he died said that he hoped he ben would prove him wrong. Ben then had Widmore banished. Widmore is now back with the list of candidates and a desire to keep man in black on island which indicates hes on the side of jacob as he was when he was the leader of the others. Widmore also could not find the island after he was banished until now which could show that he was needed now by the island. Only one thing does not make sense, when miles was off island pre freighter, he met widmore and then bram etc. took him into a van and said theres gonna be a war and your on the wrong side...