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Was Ben simply being the ultimate opportunist? He allied with MiB at Dharmaville! Was that real, or to save his skin, or to take revenge on Widmore, or to stay close to MiB so that he could undermine him.
I am aware that he looked very scared at what Smokey did to Richard (and might have done to him). Really it is hard to see why MiB didn't kill Ben anyway - what possible use was Ben to him. Why was he making offers (even though they were transparently false) to Ben (as they sat on the porch). Also he had worked with Richard for decades, yet he made no effort to stop him "negotiating" with MiB. Was giving the second walkie to Miles evidence that he wasn't with MiB or that Ben was just covering bases.
Then at the well Ben loads his magazines and looks up to see MiB packing the rope. He doesn't look like a happy man (Ben that is). Then there's that stuff about "I thought you meant destroying the Island figuratively." Oh, who is pulling whose? The master manipulator didn't understand "destroyed" as the master destroyer looked into his eyes and said "I am going to get Desmond to destroy the Island."?
O.K. if he was with MiB was the revelation that he would have to go on a yacht with MiB the last straw, so he starts helping Miles and Richard. But is he still playing opportunism or not?
Does he see a chance that he can get in with Jack and be his helper (looks like he has no intention of leaving the Island anyway, where exactly would he go?) or a bit later realizes Jack is doomed and Hugo is his best chance.
Because if he did, then Ben played the longest con of them all. He may have been No.2, but then he always had been, and frankly Hugo isn't that sharp. So if he did then it is Ben who got ALL that he ever wanted.
What do you think?