Season 1, Episode 8:
Confidence ManWhile out collecting bananas, Kate runs across some clothes and personal items on the beach, including a paperback of Watership Down. Sawyer comes up out of the water and makes with the usual innuendo, but Kate's having none of it.
Sawyer finishes getting giggety with a lady, Jessica, in a shabby hotel room. As they're cuddling, Sawyer tells Jessica that he loves her, but she notices the time and reminds Sawyer that he's late for a meeting. While dressing and rushing out, his suitcase opens and wads of cash, dozens of them, fall onto the floor. Sawyer sheepishly tells Jessica that "you weren't exactly supposed to see that."
Tromping through the jungle, Sawyer hears noises and runs to the spot where his stash of goodies is hidden, and finds Boone rifling through it. At the caves, Jack tends to Sayid's head wound, and tells him about their plan to use the transceiver to triangulate the radio tower's location. Boone, beaten to a bloody pulp, limps into the caves with Shannon's help. When asked, he admits that Sawyer did it. On the beach, Charlie brings water to Claire and tries to convince her to move into the caves, but she'd rather wait on the beach in case rescue comes. While being treated, Boone tells Jack that he was looking through Sawyer's stash for spare asthma inhalers: it's for Shannon, who has asthma, and Boone thinks Sawyer has the inhalers because he also has the copy of Watership Down that Boone checked in his luggage. (Author's Note: What, you thought I kept mentioning that book just for kicks?) Jack heads to the beach and starts looking through Sawyer's stuff for the inhalers. They almost come to blows when Kate shows up.
Sawyer explains to Jessica that the money, a hundred and forty thousand dollars, is to invest in an off-shore drilling scheme that'll triple his money in two weeks, guaranteed. He's meeting a partner who'll invest and split the profit fifty-fifty, but Jessica suggests an alternative: she gets her husband to invest, and then she and Sawyer will split the money.
Jack is willing to kick Sawyer's arse in order to get the inhalers, but Kate offers to talk to him instead. She finds Sawyer chopping wood and asks him what he wants for the inhalers. His price is a kiss from Kate, right there and then. Kate thinks that Sawyer is putting on an act to make people dislike him, and says that she's seen him reading a piece of paper he keeps in his pocket at all times. Angry that Kate thinks she knows him, Sawyer forces her to read the letter.
Kate: [reading] Dear Mr. Sawyer. You don't know who I am, but I know who you are and I know what you done. You had sex with my mother and then you stole my dad's money all away. So he got angry and he killed my mother and then he killed himself, too.
Sawyer: Don't stop now. You're just getting to the good part.
Kate: [reading] All I know is your name. But one of these days I'm going to find you and I'm going to give you this letter so you'll remember what you done to me. You killed my parents, Mr. Sawyer.Sayid questions Locke about his whereabouts the previous evening, during the attempt to locate the radio transmitter. Locke suggests that Sawyer was responsible, since he's profiting the most by staying on the Island and, using a cigarette, he could've time-delayed the fuse on the bottle rocket he supposedly set off moments before Sayid was attacked. That night, Shannon starts having an asthma attack while Sawyer brazenly walks through the camp and takes water. When Sawyer refuses, Jack starts hitting him, but he doesn't spill.
At a fancy restaurant, Sawyer discusses the investment with Jessica and her husband, David. Jessica pushes for David, who is reluctant, to invest, while Sawyer acts cautious about "business between friends". Once Sawyer shows David the cash and offers to let him hold onto it for a night, David accepts the deal.
Charlie and Claire talk about the things they miss most. Claire admits to craving peanut butter, and makes a deal with Charlie to move up to the caves if he can find some. At the caves, Shannon asthma attacks get worse. Jack realises that they're being brought on by stress and coaxes her into a more normal breathing pattern, but it's a temporary fix: she still needs an inhaler. When Jack plans to force Sawyer into talking, Sayid offers to do it instead and reveals that during his time in the Republican Guard, he was a torturer. In the jungle, Charlie asks Hurley if there's any peanut butter anywhere; Hurley says no, and gets very defensive about his size. At the caves, Sun goes to Michael and says she can help with Shannon's asthma. At the beach, Sayid and Jack knock Sawyer out, drag him into the jungle and tie him to a tree. When he still refuses to tell them where the inhalers are, Sayid starts inserting shards of bamboo underneath Sawyer's fingernails. Disturbed by Sawyer's screaming, Jack tells Sayid to stop, but when Sayid threatens to cut out an eye, Saywer agrees to talk—but only to Kate.
In a pool hall, Sawyer meets his buddy Kilo, the one who loaned Sawyer the money he gave to David, and they discuss the con he's pulling.
Sawyer: See, women are easy. A few cosmos, a couple of stunts they haven't seen between the sheets, and they think the scam's their idea. Now husbands, they need to touch the money. Smell it. Believe that if they had the brass to put that suitcase in the trunk of their family sedan and speed away, they just might have a chance at being an honest-to-gosh outlaw.Despite Sawyer's confidence, Kilo reminds him to bring back the money by tomorrow, plus an extra fifty percent, or else Sawyer will "suffer".
Kate arrives, and Sawyer offers to tell her where the inhalers are, if he gets that kiss from her. Reluctantly, she kisses him—and Sawyer admits that he doesn't have the inhalers and never did. He only had Boone's book because it washed up on the beach. Angry, Kate hits Sawyer and leaves, but Sayid doesn't believe it and goes to torture him some more. Before Sayid can reach him, Sawyer manages to get free: they fight, and Sayid winds up stabbing Sawyer through the bicep and nicking an artery. Jack sends him to the caves to get medical supplies; Boone sees the blood all over Sayid's hands and is angry he wasn't involved, but stays with Shannon rather than follow Sayid back into the jungle. Michael returns to the caves with the eucalyptus plants Sun asked him to get, but Jin sees them together and gets angry. In the jungle, Sawyer tries to bait Jack into letting him die, mentioning the kiss with Kate and telling Jack that if the situation were reversed, Sawyer would watch him bleed out.
Sawyer gets David's money and his own back, closing the "oil deal". He's about to leave with all the money when David and Jessica's young son wanders in looking for his parents. After a few moments of what could only be described as Heroic BSOD, Sawyer calls off the deal and walks out, leaving all the money behind.
Sawyer wakes up and finds Kate in his tent, with his letter.
Kate: I read it again, and then again, because I've been trying to figure out why you beat up Boone instead of just telling him you didn't have his sister's medication. Why you pretended to have it anyway. The thing that I keep coming back around to is that you want to be hated. Then I looked at the envelope — America's bicentennial, Knoxville, TN. You were just a kid, 8 maybe 9 years old.
Kate: This letter wasn't written to you. You wrote this letter. [pause] Your name's not Sawyer, is it?
Sawyer: It was his name. He was a confidence man. Romanced my momma to get to the money, wiped them out clean, left a mess behind. So I wrote that letter. I wrote it knowing one day I'd find him. But that ain't the sad part. When I was 19, I needed 6 grand to pay these guys off I was in trouble with. So I found a pretty lady with a dumb husband who had some money. And I got them to give it to me. How's that for a tragedy? I became the man I was hunting. Became Sawyer. [pause] Don't you feel sorry for me.At the caves, Sun gives Shannon a eucalyptus mixture and allows her to breathe normally again. Charlie convinces Claire to move to the caves by sharing his imaginary-yet-still-"stick to the roof of your mouth, oh, god, makes you want a glass of milk, extra smooth" peanut butter with her. Sayid decides to leave the survivors' camp, supposedly because someone needs to explore the Island but really because he is ashamed of what he did to Sawyer and wants to atone for it.