"History is a nightmare from which I am trying to awake."
-Stephen Dedalus, Ulysses
No fooling, best episode of Lost so far, and it ties a lot of what I've been saying thusfar about (personal) history together in a fairly coherent, compelling way. I even took notes on it!
Before I get all into the rigorous academicizing, some choice lines from Sawyer:
Sawyer (after "mistakenly" spilling $160,000 of briefcase money in front of his lady-friend): "You weren't supposed to see that."
Jack: "Get up [from your cushy seat so's I can punch ya in the mouth]."
Sawyer: "Why? You wanna see who's taller?"
It seems that everyone on the island (at least judging from those who have had their flashbacks featured at this point) has (had?) some biographical background that haunted them, sometimes literally, as in Jack's case with the apparition of his father. (E.g. Kate's outlaw past (a crucial part of which -- i.e. the exact nature of her crime -- which, notably, has been obliterated from the show), Charlie's dragon-chasing, Locke's pathetic loserdom, Jin's shady gig with Sun's dad and Sun's attempt to escape, not to mention her secret English lessons.) However, Sawyer is more complicated.
In trying to confront his past, he is embraced into it -- he becomes the confidence man he was looking for. Yet, at the same time, he wants to be punished for falling into and repeating his biography. As such, "Confidence Man" is the episode where History Reasserts Itself on the Island of the Eternal Now (the Eternal Nowness summed up in the 16-year old recording -- a small moment of time, repeated for 16 years -- that's suspended time if nothing else. The episode formally reaffirms this Nowness: when Sawyer asks Sayid and Jack to get Kate, we get a flashback into his life, then the episode cuts back to the present and Kate is standing there. Importantly, we don't see her walking up to where Sawyer is, which belongs to the (immediate) past. She's just there now). Take, for instance, Jack's shoulder. He grimaces when he first clocks Sawyer, because of what happened to his shoulder last episode. Sun, Jin and Michael remind of us the tensions they'd been having recently, and that Sun speaks English to Michael but without Jin knowing. Sayid's history in the Republican Guard is hashed up again, though his role as an Iraqi continually reminds us of his personal history as an Iraqi. In fact, his past has begun to surface; after torturing Sawyer, he mentions that he had sworn never to do something like that again. (Interesting that Sayid's going to map the island now -- will the hypothetical map describe the island forever?)
(HOWEVER. Locke's eye-scar was gone by the previous episode. Magic! And I mean my argument, not just the island.)
Specific to Sawyer, the episode features his letter, the hardest manifestation of an individual history thusfar (I'd argue more so than even Kate's mugshot, because the former is more readable than the mugshot -- take up this issue in the comments, I double-dog dare you). The letter is a physical reminder of the past, and that its envelope bears the Bicentennial logo on it connects national (i.e. American) history with Sawyer's past.
The episode scrambles and complicates the chronology of Sawyer's history. First, we think we find about his letter before we see the moment it ostensibly describes. Then, we find out that the letter preceded the moment where Sawyer is confronted with a child, and that the presentation has been accurate -- history has been sorted.
The action of and Sawyer's attempts to regulate his history are similarly strained. He erases, or obscures, and tries to refashion his past in several ways -- depicting himself as the con man in the letter, presenting himself a certain way to the wife -- but both of these attempts eventually fall victim to personal history. Kate discovers the truth about his writing the letter, and Sawyer can't go on with the con when he sees the son who reminds him of himself. Figuratively embodying this relationship to the past, Sawyer almost burns the letter, but at the last second, doesn't. Sawyer is trapped inextricably in his history.