James often employed his earlier con. Juliet's early attempts to save the island's pregnant women failed. After whispering something in her ear, he kissed Kate passionately goodbye. Kate awoke to find him listlessly throwing rocks at the food button in his cage. They would then all go to Hydra Island to meet Widmore, with whom he had a deal. ("Some Like It Hoth"). When Jack explained everything to the remaining survivors, Sawyer guessed that Locke didn't have what he needed, which was Desmond. He began a relationship with Juliet and they lived together during the 1970s until Jack, Hurley and Kate returned to the Island following the crash of Ajira Airways 316. Sawyer arrived at the Flame, to see that Radzinsky had already locked Sayid in a room and suggested that they shoot him. James is informed Jacob picked and manipulated those people at various points in their lives to have them show up on the Island. Sawyer and Miles, along with Aaron, continue on where they meet Jack and Kate in a small field. Following his time on the island, Josh Holloway attempted to … She insisted that they bury the bodies of the Others, and take Paul back with her. Sawyer, Kate and Juliet intercepted the DHARMA van as it headed towards the Swan station. After saying goodbye to Jack, Hurley and Ben, he and Kate jumped off a cliff and swam to the sailboat. Sawyer was nearly shot by a DI worker above him, but it was Kate who had his back that time as she shot the worker dead. Jack refused and Sawyer continued to beat him until Juliet intervened, shouting at Sawyer to stop. He led the small group until a final time shift, where they were stuck in 1974. Later as they walked back to the van, they passed Jack, who looked at Sawyer and said simply, "See you in Los Angeles". ("A Tale of Two Cities"), Sawyer and Kate were made to work in harsh conditions in a rock quarry, and during this time, Sawyer rebelled against his captors. He even knew what it felt like "to lose somebody you love". He is cared for by Kate, until her father, Wayne, is channeled through Sawyer. She succeeds in saving both Amy and her child. They climb down a cliff to a cave. Out in the jungle, Sawyer told Jack about his parents' murder-suicide, and his witness to the tragedy. As far as who the others are, it's still unclear. In the fifth season, Sawyer quickly acclimates to his new role as group leader as the remaining survivors are sent back through time, after which he falls in love and forms a stable relationship with Juliet Burke (Elizabeth Mitchell), with whom he moves onto the afterlife in the series finale. When a piece of the raft breaks off, Sawyer is the first in the water to retrieve and re-attach it. Once they reached there, they camped out when Sawyer won an argument as to whether they should look immediately for the castaways' camp. He gives the flustered Richard information able to fully convince the latter. Ben tried to prevent Sawyer from entering the house, but Sawyer and Claire made it safely inside through a window. Ben informs Sawyer they are on a smaller island, separated by a stretch of open ocean from the island on which their plane crashed. They moved through the bamboo forest and as they drew close to the Source, Locke drew his knife and said it should just be him, Jack and Desmond from here on, leaving the rest behind. He shot his wife then turned the gun on himself, while young James hid under the bed and watched. One night Locke tells Sawyer that he has captured Ben, and takes Sawyer to the Black Rock, locking him in a room with a bound and gagged stranger. Unlike his nemesis, James drew the line at harming children in his cons; seeing the boy wracked him with guilt and he did not want to force a child to go through what he had. He also refuses to help Bernard create an S.O.S. On this trip, he began to know Kate. When asked why he would not kill Ben himself, Locke responded that he was not a murderer. But it was to no avail, Juliet saw that the scaffolding was collapsing and would take all three of them down, and she told Sawyer she loved him before letting go. Juliet became annoyed when he called her "Freckles", however, and gave Kate the fence code in order to send her away. However, he later reveals his true plan to Kate: to turn both sides against each other and escape on the submarine while both sides are distracted. Ben was the one to come, but Sawyer's plan was unsuccessful, because they turned off the electricity. When Jack brought a wounded Kate into the sub, Sawyer headed to the surface hatch to grab Claire, who had remained behind fighting Widmore's men. Later, Sawyer tried to recruit help with little Ben's surgery from Jack, who flat out refused. Kate made her last bid for James to let her go, but although he seemed tempted, he told her it was not going to happen. Sawyer argued that Jack was making a mistake and that he, Jin, Hurley, and Juliet would meet them at the beach when their plan inevitably fails. He initially accuses Sayid of being the terrorist who caused the crash. They washed up on shore and met up with the previously unknown tail section survivors of Flight 815 and returned to camp. Their emotional goodbye, and that kiss on the cliff...a definite pass-the-Kleenex moment. During their trek, they encountered a strange boy in the jungle. They are in the past. Referencing to Ben, Hurley, Sawyer & Kate. 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