Plus, wouldn't a 'real' conman know how to talk to a woman. I mean, he didn't have to be honest at that point, he could have pretended he was conning everyone into letting him stay. I think that shows that Sawyer.. uhh, James Ford, is not a real con man, just a soft hearted guy who was fooled real bad, and one too many times.
Plus, I said this once before, he is reading all of the books that the Other's society seems to be based upon. I believe, when it all comes down to it, Sawyer will be the leader of the new occupants of the others camp, except it will be the chosen Losties, and not the Others, Smokey will deal with them.