The contents of the letter that we've seen Sawyer with previously are finally revealed and appears to reveal a pretty straightforward scenario. Sawyer, the con artist, destroys a marriage and a family with one of his scams and now hates himself for it. Of course, with Lost, it's never that simple, and as the episode eventually reveals, the man we know as Sawyer was the victim of a confidence man's scam when he was young. It's a terrible tragedy but it's the genesis of a fascinating story arc for the character that, so far, has played the 'bully' of the show.
The success of this episode begins and ends with Josh Holloway. So far, we know that he's good at playing Sawyer: The Tough Guy, but now he has to sell a multilayered fragment of a human being who hates himself for becoming the man who destroyed his family. Holloway succeeds in creating a character that quickly unravels throughout the episode as his terrible secret is revealed. The flashback is played well in parallel with Sawyer's letter and the final scene is perfectly handled. Sawyer successfully cons a couple into giving him a large amount of money and then walks away after seeing their son. A harsh reminder of the man he has become and the man he hated as a child. Holloway does an exceptional job of conveying Sawyer's disgust as he realizes what he was about to do.
Sawyer's relationship with Kate is explored and it's a refreshing change after having 'Jack & Kate' forced upon us for the last several episode. As much as Jack and Kate appear to be better suited as a couple, Sawyer and Kate share far better chemistry. It's obvious they share a far deeper bond and that Sawyer has a superior understanding of Kate than Jack ever will. On the other hand, Kate gravitates towards Sawyer because she feels more comfortable around someone that she feels is at her level. It's a courtship that is doomed from the beginning but interesting to watch nonetheless.
Shannon's asthma is a serviceable enough device to get the ball rolling and brings a couple of stories together. Sayid and Jack desperately require the asthma medication that Sawyer is supposedly withholding and this leads to drastic measures. The torture scene was still fresh in my mind from the original airing of the episode and it still had the exact same impact as it did then. This is the first time we witness "bad ass" Sayid in action. Seeing him standing before Sawyer, sharpening the sticks of bamboo, is a frightening visual. Jack on the other hand, as much as he wants that medicine, isn't quite prepared to go this far. Still, almost as if he is biting his tongue, he allows the torture to commence. Remember, they've only been on the island for about ten days. It's interesting to see how being ripped from civilization is already having an effect.
"Confidence Man" is yet another excellent character piece. One of the reasons Season 1 is still regarded as a favorite by some is due to episodes that skillfully develop these characters that we have known for such a short period of time. The relationships are developed in a realistic and fascinating way. Later seasons tend to utilize shock value for their big moments so it's a little refreshing to be reminded that the show didn't always rely on that crutch. Admittedly, I still love those big shocking reveals.