Contains spoilers for this episode and earlier episodes.
In flashbacks, Sawyer uses an affair with Jessica to arrange a fraudulent investment involving her husband's money. A deliberately opened briefcase makes the deal appear genuine, although the cash belongs to an impatient creditor. Sawyer visits the couple to complete the scheme, then sees their young son and abruptly abandons it. The child interrupts his willingness to take the family's savings, leaving him without the proceeds he had planned to use to repay his own debt.
Shannon's breathing difficulties lead Boone to search Sawyer's belongings for missing inhalers, provoking a beating. Jack suspects Sawyer is hoarding the medicine, and Sayid tortures him with Jack's approval. Sawyer demands a kiss from Kate before providing an answer. She agrees, only to learn he never had the inhalers. Sayid attacks him in anger and cuts an artery in his arm. Jack treats the wound while Sun helps Shannon breathe with a plant-based preparation.
Kate returns to the letter Sawyer carries and realises he wrote it as a child to the confidence man who destroyed his parents' lives. Sawyer admits that he later took the man's name and became a con artist himself. He rejects her sympathy and orders her away. Ashamed of torturing him, Sayid leaves camp to travel along the shore. Sawyer considers burning the letter but cannot finish the act, keeping the account of his childhood loss.