“Confidence Man”

Lost season 1, episode 8
Original air date: November 10, 2004

Backstory:
Sawyer's lady friend reminds him that he has a business meeting to attend, so he reluctantly removes himself from being in bed with her. As he gets dressed and picks up his briefcase, it falls open, revealing a large amount of cash that she wasn't supposed to see. Sawyer explains that his meeting is to line up an investor to buy oil shares: if he can come up with $300,000 to buy a share, a government program will kick in money that will triple his investment within a month.

It sounds too good to be true, and it is, but the woman convinces Sawyer to let her be his investor — with her husband's money, that is. Sawyer meets with her and her husband, who is wary of this scheme, especially since he doesn't know Sawyer personally; Sawyer works at a car dealership with his wife. But Sawyer offers to let the husband hang onto Sawyer's half overnight while he thinks about it. That changes the husband's mind, and they arrange for Sawyer to pick up their $150,000 at their home.

That's where things start to sour: Sawyer's already in debt to someone else, a big black man who doesn't seem to play games. The upfront cash that Sawyer let the husband hang onto belonged to this other guy, and he's none too happy with Sawyer for letting someone else handle it. Moreover, when Sawyer shows up at the couple's house to pick up their money, their little boy turns up. When Sawyer sees the little boy, he calls off the deal and walks away.

Current:
When Shannon begins to have asthma attacks and has run out of her medication, Boone rifles through Sawyer's private stash to find inhalers. He believes that Sawyer has the four extra inhalers that Boone had packed for Shannon, because Sawyer has Boone's copy of Watership Down, which had been in the same luggage. Sawyer beats Boone up, and when Jack finds out, he goes after Sawyer. Kate steps in before they can beat each other up, though.

Kate confronts Sawyer directly about the inhalers, and Sawyer says he'll hand them over in exchange for a kiss from Kate, which she declines. She asks Sawyer why he's like this — so anti-social and seemingly unfeeling. She says she's seen him with a letter that obviously means something to him, so she knows that he's got feelings. Sawyer shows her the letter: it's from a little boy, starting "Dear Mr. Sawyer, you don't know who I am, but I know who you are." The boy goes on to say that his father killed his mother after finding out that she was having an affair with Sawyer, and then killed himself. He also accuses Sawyer of stealing all his dad's money. He closes by saying someday he'll find Sawyer and hand-deliver the letter.

When Shannon's attacks get worse, Jack and Sayid decide to abduct Sawyer and torture him to make him reveal the location of the inhalers. They tie him to a tree and smash reeds under his fingernails and so forth. He eventually says he'll tell Kate where the inhalers are, but only Kate. When she arrives, he demands a kiss again, which she reluctantly gives — reluctant at first, perhaps, but they both lean into it. When they pull apart, Sawyer reveals that he doesn't have the inhalers. Kate asks about the book, and Sawyer says it washed ashore. When she tells Sayid and Jack, Sayid attacks Sawyer and ends up putting a knife through Sawyer's arm.

Jack sews Sawyer up, and Sayid decides to leave the group. He says he promised himself he would never be violent again, long ago, and he fears that he'll break his promise if he stays. He tells Kate he's planning to map the island by walking the shoreline. Meanwhile, fortunately for Shannon, Sun has made a poultice of eucalyptus leaves that quiets her attacks. Kate confronts Sawyer about his actions, and he reveals that the letter he carries wasn't for him, it was from him. The man who destroyed his family was Sawyer, and he spent his childhood hating and searching for him. Then, when he was a teenager, he got himself into the confidence game and started behaving just like the man he had always hated. Now, he is Sawyer.