Kate is out collecting bananas when she comes across a copy of the book Waterhsip Down on the beach. She looks over to find Sawyer taking a swim. He emerges naked from the surf and shamelessly flirts with her. As Kate questions if his tactics work on all the girls, we FLASHBACK to Sawyer in bed with a woman named Jessica ? and his southern charm has certainly worked its magic this time around. They bask in the afterglow and seem very much in love. But Sawyer hops out of bed, claiming that he's late for a meeting. When he reaches for his briefcase, it spills open, revealing bundles of cash.
Back in the jungle, Sawyer approaches the hiding spot where he keeps his stash and finds Boone going through his things. Off Boone's scared expression we go to the caves, where Jack tends to Sayid's head wound as Sayid explains that whoever hit him also destroyed the transceiver. Sayid vows to find the person responsible. Boone stumbles back into camp, bloody and beaten. He explains that Shannon has asthma and has run out of refills for her inhaler. He went to see Sawyer because he caught him reading Waterhsip Down ? a book that Boone had in his bag; the same bag that carried the refills. Boone tells Jack that Sawyer refused to give up the refills and attacked him.
On the beach, Charlie delivers water to Claire. He tells her that he's worried about her and attempts to talk her into moving to the caves. But Claire wants to stay on the beach, holding onto hope of rescue.
Jack confronts Sawyer about with-holding the inhaler refills that could help Shannon. He begins rifling through Sawyer's things and the two almost come to blows, but Kate interrupts them, diffusing the tense situation. Jack leaves Sawyer, who pulls out a familiar piece of paper ? one that we recognize from the pilot ? and begins to read, which launches into a FLASHBACK ?
? to the hotel room where we last left him. Jessica is more than curious about all the cash Sawyer has in his briefcase. Sawyer explains that it's his life savings ? $140,000 ? but only half of what he needs to buy into a share of an oil mining operation. He's meeting with an investor who may supply the other half. Jessica's intrigued and offers a way to get the rest of the money without the investor ? through her husband.
Back on the island, Kate tries to calm Jack down. She offers to talk to Sawyer, claiming she can reason with him because, "they have a connection". Kate approaches Sawyer and attempts to appeal to his sense of capitalism. She asks what he wants in exchange for the inhaler refills and Sawyer requests a kiss. Kate doesn't buy that this is what he wants and tries to get under Sawyer's skin by mentioning his 'letter' ? the one she's seen him read several times before. Sawyer turns dark at the mention of the letter, forcing Kate to read it out loud. We learn that the letter was written by a young boy who implicates Sawyer in a scam against his parents, which led to an affair with his mother, driving his father to kill his mother and then himself. Meanwhile, out in the jungle, Sayid questions Locke on his whereabouts when he was attacked. Locke claims he was out hunting and points Sayid in Sawyers direction ? someone who's been profiting from their current circumstance. Locke gives Sayid one of his knives to protect him from another potential attack.
At the caves, Shannon is in the throes of an asthma attack, as Sun looks on concerned. Sawyer strolls into camp for water, which infuriates Jack, who finally takes a satisfying swing at him. But Sawyer is defiant and doesn't fight back. Jack is left to walk away and off Sawyer's look we ?
? FLASHBACK ? to an upscale restaurant, where Sawyer, posing as Jessica's co-worker at the bank, explains the oil opportunity to her husband, David. But David is skeptical. Sawyer seems unphased and walks away, but David has second thoughts and calls out to Sawyer, who stops with a grin plastered across his face. Sawyer leaves the money with David in an act of good faith and tells him he'll wait for a decision.
Back at the beach, Charlie and Claire discuss the comforts they miss at home ? but all Charlie can think of is food. Claire admits that she too misses food and is especially craving peanut butter. Charlie makes a deal with her ? if he produces peanut butter, she moves to the caves, where, at the moment, Shannon is having a much more severe attack and Jack has to talk her down. He storms out to confront to Sawyer again. Sayid follows him and suggests that he knows a way to get what they want out of Sawyer ? he was, after all, in the Iraqi Republican Guard. And Jack, having had no luck at reasoning or fighting with Sawyer, can only agree.
Meanwhile, Charlie hunts for peanuts to make peanut butter, while Sun shares a remedy for Shannon with Michael. On the beach, Sayid sneaks up on Sawyer while he's sleeping and clubs him over the head. He and Jack drag Sawyer out into the woods and tie him to a tree, much to Kate's objection. Jack attempts to reason with Sawyer one last time. But when Sawyer refuses to produce the inhalers, Sayid goes about torturing him with bamboo reeds under his nails. Jack can barely stand to watch and calls Sayid off. But there's more going on here for Sayid, who thinks Sawyer is the one who attacked him in the previous episode. Sayid pulls out Locke's knife and threatens to put it through Sawyer's eye. This gets Sawyer to agree to talk ? but only to Kate.
In FLASHBACK ? we visit Sawyer in a pool-hall, where he explains to his to his 'boss', Mr. Kilo, that he left his money with the mark in order to earn his trust. He explains that the wives are easy, but that the husbands need to think they're smarter than him. Kilo tells Sawyer he had better be right and demands his money, plus fifty percent, by noon the next day.
Back on the island, Sawyer wonders if Kate is going to let Shannon suffer over one little kiss, which he asks for shamelessly and she agrees to selflessly ? but what starts as a mercy kiss turns into something more?there's chemistry between them and she may actually be enjoying it. When they break, Sawyer announces that he really doesn't have the inhalers; the copy of Waterhsip Down simply washed up on shore. And Kate smacks him, hard. She tells Jack and Sayid that Sawyer doesn't have what they need. But Sayid maintains that Sawyer is lying and goes back to resume his torture to find that he has worked himself free from the ropes. Sayid attacks Sawyer wielding Locke's knife. They tussle and Sawyer ends up with a slashed artery. Jack pinches off the blood flow, literally holding Sawyer's life in his hands. He sends Sayid to get medical supplies. And as Sawyer drifts in and out of consciousness ?
? we FLASHBACK a final time, to David and Jessica's home, where Sawyer is about to close the deal and walk away with $300,000. But when David and Jessica's young son emerges from the bedroom, Sawyer can't bring himself to do it. He calls things off, inadvertently reveals his affair with Jessica and leaves the money behind.
Back on the island, Sawyer sleeps, recovering with a few stitches in his arm. He wakes up to find Kate sitting nearby with his letter. She explains to him that since she first read it, she's been feeling that something wasn't quite right. So she continued to read it ? over and over again, when it occurred to her that he wrote the letter ? and a 1976 Bicentennial postmark on the envelope confirms it. Sawyer admits that he was just an 8 year old kid when he wrote it. He explains that when he was nineteen, he got into trouble where he owed a lot of money to some very scary men, so he took the name of the man he was hunting and became a "confidence man" himself. But just when we think Sawyer is softening by opening up to Kate, he shuts down and chases her away.
Elsewhere, Sun brings eucalyptus leaves to Shannon, helping her to breathe, while Charlie brings some 'imaginary' peanut butter to Claire and convinces her to come to the caves. Sayid tells Kate he's leaving the camp because he can't face what he did to Sawyer ? he plans to walk the shore and map the island. And Sawyer takes a lighter to his letter, about to burn it, but he's unable to go through with it and pockets the letter, right along with his anger?
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