Season 1, Episode 8:

Confidence Man

While 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.

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.

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.

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.

Tropes in this episode include:

• All for Nothing: Everything Jack, Kate, and Sayid do to try and get the inhalers from Sawyer turns out to have been pointless; he never had them to begin with, and only dragged things out because of his own self-hatred. The inhalers themselves ultimately don't come into play at all; Sun treats Shannon's asthma using eucalyptus, which Jack kicks himself for not thinking of.
• Attack Hello: When Sawyer wakes up from a nap, Sayid says "Good morning," and hits him with a pipe.
• Aw, Look! They Really Do Love Each Other: After they've done nothing but bicker in the time they've been on the Island, Boone shows genuine concern for Shannon during her asthma attacks, while Shannon asks him to stay and comfort her when he wants to help Sayid torture Sawyer.
• Bait-and-Switch: The episode seems to be building up to Sawyer conning David and seducing Jessica, leading to their deaths in a murder-suicide and then...he backs down. It is revealed the flashbacks were not about the events in the letter but rather him realizing he's gone down the same path as the man who ruined his life.
• Beneath the Mask: Beneath Sawyer's rough and snarky exterior hides a deeply wounded, self-loathing man, something Kate figures out by the end of the episode.
• Cassandra Truth: Sawyer eventually admits that he never had the inhalers. When Kate relays this information to Sayid, he refuses to believe it, and it takes nearly killing Sawyer before Sayid comes to his senses.
• Chekhov's Gun: Sawyer has been reading a paperback of Watership Down for the last couple of episodes. Here, it's revealed that the book belonged to Boone, and it sets off this episode's conflict.
• The Chew Toy: Sawyer gets the first of what will be multiple severe injuries while on the Island.
• Compressed Vice: Shannon has an asthma attack and is at risk of dying without her inhalers. Aside from a brief clip of Boone handing her the inhaler in a flashback montage in the season finale, and a Brick Joke where Jack and Hurley find the inhaler in the jungle in Season 6, Shannon's asthma is never mentioned in any episode of the show before or after this one.
• Continuity Nod: After punching Sawyer, Jack grips his shoulder in discomfort, having dislocated it in the previous episode. After the punch, Sawyer reminds Jack that he's been saying they're "in the wild" from the beginning.
• Death Glare: Sawyer gives one to Kate after she gets a little too close to the truth in her assessment of him. He doesn't let up until she's finished reading the letter and can't look him in the eye.
• Death Seeker: As Jack tries to staunch the bleeding from his knife wound, Sawyer tries to convince him to just let him bleed out, even saying that if their positions were reversed, Sawyer would just let him die.
• Defiant Captive: While bound and tortured, Sawyer just keeps taunting Jack and Sayid. It's only when Sayid threatens to cut out one of his eyes that Sawyer breaks, and even then, he drags it out, insisting that he give the information only to Kate, and only after she gives in to his demand for a kiss.
• Don't You Dare Pity Me!: After telling her his story, Sawyer becomes angry at the look of sorrow and sympathy on Kate's face, ordering her to leave him alone.
• Everyone Has Standards: In the flashbacks Sawyer breaks off a con when he sees the couple he's been scamming have a young son. He doesn't want to be responsible for what happened to his parents happening to someone else. He even leaves all of the money with the couple he'd been trying to con as he departs, despite having been threatened by his partner in the crime.
• Eye Scream: Sayid threatens to cut out one of Sawyer's eyes when he keeps refusing to tell them where to find the inhalers.
• Fanservice: The episode opens with Sawyer walking out of the ocean naked (only seen from the waist up) completely shameless in front of Kate.
• Fingore: Sayid tortures Sawyer by driving sharpened pieces of bamboo under his fingernails. Sayid's description implies that he's done it before.
• Foreshadowing: Sawyer's reaction to seeing David and Jessica's son foreshadows what Kate deduces at the end of the episode, that Sawyer's letter wasn't written to him, but by him.
• Get Out!: Sawyer yells this to Kate after telling his backstory.
  Sawyer: Get the hell out. [voice breaks] Get out!
• Good Cop/Bad Cop: During Sawyer's interrogation, Jack tries to reason with Sawyer, and when that gets them nowhere, Sayid starts torturing him.
• Good Is Not Soft: Given that the alternative is letting Shannon suffer and possibly die, Jack and Sayid are willing to torture Sawyer to force him to give up the medicine to save her.
• Hollywood Kiss: Kate and Sawyer's kiss is a deliberate aversion. Evangeline Lilly and Josh Holloway agreed that they didn't want to do a "perfect" kiss, but let it be as awkward as two sweaty people living in a jungle would realistically be.
• Horrible Judge of Character: The normally astute Sawyer severely misjudges Sayid.
  Sawyer: You know what I think, Ali? I think you've never actually tortured anybody in your life.
  Sayid: Unfortunately for us both... you're wrong.
• I Kiss Your Hand: Sayid does this to Kate before the leaves the survivors' camp and tells her he hopes they see each other again.
• Jack Bauer Interrogation Technique: Sayid tortures Sawyer for the whereabouts of Shannon's inhalers. Sawyer doesn't have them and never did, but he allows Sayid to believe he does and continue torturing him out of self-loathing and spite.
  Sayid: I served five years in the Republican Guard.
  Jack: I thought you were a communications officer.
  Sayid: Part of my training entailed getting the enemy to communicate. Just give me ten minutes with him; he'll give us the medicine.
• Let the Past Burn: Subverted; after all is said and done, Sawyer contemplates burning his letter to "Mr. Sawyer", but can't bring himself to do it.
• Kick the Dog: Sawyer spends nearly the entire episode doing this in one way or another; he beats up Boone rather than admitting that he doesn't have Shannon's inhalers, pretends to have them throughout the episode, feigns indifference to her plight, demands a kiss from Kate in exchange for giving up the inhalers, and even taunts Jack as he tries to stop Sawyer from bleeding to death. Kate figures out at the end that he was actually invoking the trope all along; he wants to be hated.
• Kubrick Stare: Sawyer shows that he is pretty good at it, several times.
• My God, What Have I Done?: Once he calms down, Sayid is deeply regretful at having tortured Sawyer and leaves the camp in self-imposed exile.
• O.O.C. Is Serious Business:
  • When Kate (more accurately than Sawyer wants to admit) sees through his bravado at the wounded man he really is, Sawyer drops his usual charm and wit, snarls at her to shut up, and shoves his letter in her hands, demanding she read it. Kate is visibly taken aback at his change in demeanor, and even moreso after reading the letter.
  • When Kate figures out that he wrote the letter, Sawyer quietly calls her by her actual name, rather than using a nickname.
• Refuge in Audacity: When Sayid questions Locke on his whereabouts when he was attacked, Locke not only admits that he doesn't have any solid alibi (claiming he was skinning a boar and thus no one can verify his claims), but then immediately comes up with a hole in Sawyer's alibi. Since Sayid was already looking for a reason to go after Sawyer, he falls for it with no hesitation.
• Self-Imposed Exile: Sayid exiles himself from the group because of his guilt in torturing Sawyer.
• Sexy Surfacing Shot: Sawyer strides out of the ocean completely naked in front of an unimpressed Kate.
• Shout-Out: Hurley describes Jack talking Shannon down from an asthma attack as a "Jedi moment".
• Spotting the Thread: Kate figures out that Sawyer wrote the letter he carries around when she notices a stamp on the envelope from 1976, when Sawyer would have only been a child.
• Teeny Weenie: When Sawyer walks out the water naked in front of Kate, she looks him up and down... and makes a crack about the water being cold.
• You Are What You Hate: After telling Kate about his childhood tragedy, Sawyer admits that, as an adult, he fell into the life of a confidence man to get out of a tight spot. Indeed, when he first gave Kate the letter, he allowed her to believe that he was the "Mr. Sawyer" the letter was addressed to, driving home how much he hates himself for becoming like the man who destroyed his family.
  Sawyer: How's that for a tragedy? I became the man I was hunting. I became Sawyer.