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I thought it kind of seemed obvious that Jack would be following Hugo pretty soon. Just the whole role reversals going on all over the place, and their fatal flaws would have to be the need to, respectively, lead (Jack) and follow (Hugo). Also, Hugo's line about it being so old-school, them running around the jungle. Well, I was thinking, when Jacob was talking to Hugo outside the lighthouse, and told him that with some people you can just get in a cab, hand them a case and tell them to do something, and some people have to be given time to ponder, and that Jack NEEDED to see how important he was. Even though he is a man of science, Jack has helped renew people's faith in life many times (Charlie, Rose, Hugo). So, what if Jack is only so important because he is the one that can give Hugo the confidence he needs to trust himself? I mean, if stubborn, self-righteous Jack has faith in Hugo---what better self-esteem boost and confidence-giver?