I think the drunk pilot used to fly for Dharma. That's why he might know the area so well to be able to fly. And the guy that looks like Luke Perry is a physicist expert in the field electromagnetism, which Dharma was studying on the island.
This guy in particular, Miles Straume, I think is the son of the doctor in all the Dharma orientation films. They look very much alike. One would have to think the casting was specific in that manner. Also, we've had a lot of story lines about sons being pissed off at their fathers. How about one about a son who looks to revenge the death of his father? That's why the four are there. To avenge the death of those they love that died in the purge.
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As for the "man" Ben has on the boat...I thought Michael at first, but now I'm rethinking. Now I don't even think it's a man. I think it's a woman. The woman he shot, Charlotte. I think that's one reason he shot her because he knew she'd be donning a vest and not be fatally wounded. She also seemed to know where to dig for a Dharma polar bear in the Tunisian desert. Maybe she knew about their past experiments.
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Theories. Need them. Make it happen.
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