Sometimes everything you need to know about an episode of LOST comes from the title. That’s surely the case here. Confidence Man is an episode about the art of the con, and the different confidence men (and women) who practice it. And it’s certainly the case that the episode title is a clue to character connections, or at the very least represents the prevailing sort of relationship at this juncture in the Losties’ adventure on the Island. In fact, I think we can safely say at this point that everyone featured in this episode is either a con artist of one kind or another, and many of them are simultaneously marks as well.
Obviously, of course, we have Sawyer, both on the Island and in the Flashbacks. We’ll get back to him in due course, for this is what we’d expect given the episode title. Instead, let’s begin with some of the less obvious con artists running about. Because, I mean, it’s not exactly apparent that everyone is a con artist, or who their marks are. Some, of course, are obvious simply from what we’ve seen prior to Confidence Man. Kate, for example. She lied to the farmer, Ray Mullen, about her identity back in Tabula Rasa, when she was a fugitive on the lam hiking across Australia. When hiking up the mountain with Sawyer, Sayid, Shannon, Boone, and Charlie, after Sawyer shot the polar bear, she feigned ignorance regarding how to use and dissemble a handgun. And yet, in this episode, she doesn’t seem to be conning anyone: she’s the subject of Sawyer’s con to get a kiss.
But upon closer examination, doesn’t she kind of go out of her way to figure out Sawyer himself and his story? She doesn’t have to get so deeply enmeshed in the episode’s drama, but she dives right in anyways. The seminal moment, I think, is when they kiss. Because up to that point, she’s expressed a tremendous amount of disgust towards Sawyer, but that kiss betrays a passion that’s the antithesis of disgust. She’s played the part of “the good girl” with him, with a certain amount of righteousness, but this is just cover for her true feelings. Kate, as it turns out, is really good at the art of con.
Charlie is, too. He wants Claire to move to the Caves with him, but she’s all, like, preferring to stay on the beach and shit. However, there’s something she really wants – peanut butter. So she manipulates Charlie into finding peanut butter on the Island. Of course, Charlie can’t find any peanut butter. There isn’t any to be found, much to his consternation. So Charlie does his best to con Claire by pretending that he has, in fact, found peanut butter. But all he can actually offer is an empty jar. Only through the power of his imagination can he convince her to enjoy the creaminess of emptiness. And he succeeds. She agrees to move to the Caves.
Another con artist actively plying the trade is Sun. …