Origin: Thanks to time travel, Sawyer watched Aaron's birth
Since Then: Sawyer never approached Aaron's mother, according to Hurley, but he eventually did, at Hurley's suggestion. They later discovered that Sawyer's voice kept Aaron from crying. When Claire abandoned Aaron and joined the Man in Black, Sawyer took the baby and later passed him to Kate, who eventually raised him. Sawyer presumably saw Aaron after escaping the island - his friends Kate and Claire planned to raise him together, and Aaron had become friends with Sawyer's daughter Clementine.
Origin: Sawyer is captured by Ana Lucia and the "Tailies" and Sawyer resents her leadership.
Fuel: Sawyer hated being in captivity, and hated answering to a woman even more. ("Adrift") He defied Ana Lucia at every chance, despite suffering from a gunshot wound. The more Sawyer defies her, the more determined Ana Lucia became to prove her authority. ("Abandoned").
Resolved: Yes. Sawyer and Ana Lucia formed an unlikely bond before her death. ("Two for the Road")
Since Then: Before the crash, Sawyer, a con man, has, by and large, deceived and used people to gain an advantage, usually women like Mary Jo and Jessica. He has used one particular con on several occasions that involved him seducing married or recently divorced women, then alluring them to 'invest' on a phantom deal using their husband's money or their alimony, which he would then swindle. During one such instance, he tried to pull this con on Cassidy, a recent divorcee, who caught on to his con fairly quickly. Instead of turning him in, she requested him to teach her how to con, and he obliged. Over time, he claimed to have developed feelings for Cassidy. Ultimately, however, Sawyer ended up pulling a long con on Cassidy, swindling both her and an associate he was working with on obtaining Cassidy's money. Cassidy reported Sawyer to the authorities, and he went to jail. After about a year after he conned her, she visited him in jail and told him that she gave birth to their daughter, Clementine. Sawyer denied vehemently to being the father, but he later opened up a bank account for Clementine from the money he acquired in a prison con on a fellow inmate.
Origin: Locke took Charlotte hostage while Sawyer was part of his group.
Since Then: The two only knew each other briefly while alive. Sayid retrieved Charlotte from the Barracks soon after she she entered them. Sawyer next met her when the time flashes began. Impatient for an explanation, he even threatened hitting her, and he later angrily demanded she translate Jin's Korean. Charlotte died soon after. In the flash sideways, the two met on a blind date and spent the night together. When Charlotte discovered James's folder covering his search for the original Sawyer, he kicked her out of his house. He later visited her apartment with a flower and some beers, but she rejected his apology. He left the flower at her doorstep. The beers went home with him.
Origin: Sawyer saw Desmond aboard the Elizabeth when its arrival interrupted a funeral.
Since Then: Sawyer and Desmond barely interacted during the series. Sawyer was away when the survivors first met him in the Swan. Soon after his return, Sawyer again left the camp, now kidnapped by the Others. Sawyer returned, and the two spent about a week in the same camp, and Desmond helped Sawyer hunt a boar to share with the survivors. When Desmond returned from his and Charlie's Looking Glass mission, James heard Desmond deliver the news. Sawyer then joined Locke's camp, and Desmond flew to the freighter, and the two didn't meet again till the series finale. Sawyer went to a well to try and save Desmond but found the man already gone. The two later walked to the Heart of the Island together.
In a flash sideways, Desmond turned himself in to Sawyer after running over Locke.
Origin: Hurley originally spoke against Sawyer, calling him a "chain-smoking jackass."
Since Then: Hurley's personality seemed to win Sawyer over; he uncharacteristically gave Hurley the flight manifest for free. The two bonded in later weeks, such as when Hurley helped Sawyer find a tree frog that was bothering him. Sawyer also helped spark Hurley and Libby's relationship and then later helped share the news of her death. Sawyer's insults got to Hurley though, and he once attacked Sawyer till Jin split them apart. When Sawyer returned from being kidnapped, Hurley was relieved that he was alive and began grooming him as the survivors' next leader. He also challenged Sawyer to a game of ping-pong, successfully keeping him from using nicknames for a period. They together saved Sayid, Bernard and Jin when the Others held them hostage.
When the camp split, Hurley and Sawyer became roommates, and Sawyer postponed escaping the island so he could bring Hurley as well. Only Hurley escaped the island, and they didn't meet again for three years. When they did meet, Hurley again hugged him yelling "You're alive!" Sawyer escaped the island again, and Hurley left the island after becoming Protector, so the two presumably met again after the series closed.
Prize: Kate's affection, control of resources, leadership for the survivors, justice for Juliet's death, and later the opportunity to flee from the island.
Fuel: The two have constantly competed for Kate's attention. Their fight over Shannon's inhaler is a perfect example of this - Jack believed that Sawyer had Shannon's asthma medication. Sawyer didn't, but refused to say, even after Jack and Sayid tortured him. Instead, he used the possibility as a bargaining chip for a kiss from Kate ("Confidence Man"). Sawyer took much of the control over the Losties away from Jack with his con to get the guns. ("The Long Con") Kate herself exacerbated the situation by confessing mixed emotions to Sawyer and then kissing Jack. ("What Kate Did") Sawyer was also perturbed to learn that Kate and Jack had been "caught in a net." ("?") Later, during their captivity, Jack found a monitor showing an intimate moment between Kate and Sawyer. Instead of letting Sawyer die, Jack helped them escape in a selfless act ("I Do"). This rivalry was revisited after Sawyer was left stranded in the island on 1974 spending three years living with the Dharma Initiative. When Jack returned to the island from 2007, he and Sawyer disagreed on how to handle their return. This was complicated when Sayid was captured by the Dharma Initiative ("Namaste"). Later, Jack intended to detonate a hydrogen bomb in the island, and Sawyer disagreed with him not wanting to leave the island ("Follow the Leader"). Sawyer and Juliet eventually left in the submarine, but she convinced Sawyer of returning. The rivalry reached its climax when Sawyer confronted Jack and told him that his return had ruined his life on the island. After fighting, Juliet convinced Sawyer of letting him do what he wanted to do ("The Incident, Part 1"). Sawyer attacked Jack when the Jughead plan failed and then threatned to kill him if Juliet died. He later told Kate, after Juliet died that he wouldn't kill Jack cause he wanted him to suffer.("LA X, Part 2") Sawyer later puts his differences with Jack aside and allows him to partake in his plan to flee to Hydra Island on Desmond's Sailboat, and eventually from the island for good. However, Jack and Sawyer find themselves at odds once again when Jack expresses doubt in Sawyer's plan, believing that fleeing would not be a part of their destiny, and that they have a bigger purpose back on the island. Jack's desire to return to the island infuriates Sawyer and revives the enmity between the two men. Sawyer then orders Jack to leave the boat ("The Last Recruit"). The two are reunited shortly after Widmore's attempts to kill them forces a brief alliance between the survivors and The Man In Black. The two board the submarine with their fellow survivors, only to find that The Man in Black had planted a bomb that was timed for explosion. Jack tells Sawyer to have faith in his word that the bomb would not explode, but Sawyer agonizingly tells him that he does not and tries to diffuse the bomb. However, his attempt only accelerate the bomb's countdown. Jack and Sawyer narrowly escape with Hurley and Kate before the submarine explodes, but the rest of the survivors die onboard.("The Candidate")
Resolved: Yes. Jack comforts Sawyer in his guilt for his role in the deaths of Jin, Sun, and Sayid, telling him not to blame himself, but rather The Man in Black ("What They Died For"). When the two eventually part ways for good, Jack wishes Sawyer luck, while Sawyer thanks Jack "for everything," cementing the mutual respect that had eluded them for years. ("The End")
Origin: Sawyer was one of the first English speakers Jin contacted on the Island. He traded Jin a fish for the last of his water.
Since Then: The two left the Island together on a raft, and when the Others shot Sawyer, Jin dove into the water to save him. The two spent the next days together, prisoners of the tailies. Sawyer soon learned of Sun's pregnancy and jokingly congratulated Jin, though he knew the man didn't understand. The two reunited happily after the Others kidnapped Sawyer, and they together helped Hurley start the DHARMA van. Sawyer began teaching Jin how to speak English, and when he thought the Others captured Jin, Bernard and Sayid, Sawyer decided to go to the beach to rescue them. When the freighter blew up, Sawyer thought Jin died on it, but the two shared another reunion during the time flashes. They ended up working together in the DHARMA Initiative for three years as security officers. When they traveled back to 2007, both spent time in the Man in Black's camp. Some of Jin's last words were to Jack, asking that he save Sawyer rather than stay to help him and Sun. In a flash sideways, Sawyer tried to protect Jin from an escaped killer, but Jin just smiled at him, hoping to see him at the church.
Origin: Juliet initially had decided to leave the island on the sub ride offered by The Dharma Initiative. Sawyer persuaded her into waiting with him for two weeks for Locke to return. By the three-year mark, they are living together, happily, as a couple and as members of the Dharma Initiative.
Since Then: However, when Jack, Kate and Hurley return to the island, Juliet appears worried, and expresses her fears to Sawyer by asking him whether their attempts at "playing house" are over. Sawyer reassures her that "nothing's changed". Juliet, however, remains skeptical and Sawyer continues to be drawn to Kate. When young Ben gets shot by Sayid, Kate attempts to take him to Richard and The Others for help, per Juliet's suggestion. When Sawyer decides to help Kate, she asks him why. Sawyer tells her that he's doing it for Juliet. During a group meeting to discuss their plans after imminent exposure of his con, Sawyer tells Jack that he and Juliet are heading back to the beach, and tries to coerce Kate into joining them by calling her, "Freckles". This displeases Juliet, who promptly gives Kate the combination to the sonic fence. During their interrogation after their capture, Sawyer negotiates a deal with the DI that would ensure a ticket on the sub for himself and Juliet in exchange for information on Jack and Kate's whereabouts. Juliet tells him that she's glad that he talked her out of leaving on the sub three years ago. They exchange "I love you"s, but things become awkward when Kate joins them on the sub. Juliet tells Sawyer that they're going back to help Kate from furthering Jack's plan. They meet up with Bernard and Rose. When Bernard mentions spending their lives together, Juliet catches Sawyer staring longingly at Kate, and she tells Sawyer that she's "changed her mind." Sawyer is puzzled and asks her why. She tells him that, although they love each other, they were never meant to be together. She tearfully tells him that she would rather have never met him, than lose him. During the Incident, Juliet's life is threatened when she's pulled into the Swan's electromagnetic chute via metal chains that have wrapped around her body. Sawyer clings onto her hand, repeatedly beseeching her to not "let go". When Juliet sees that the structure above him will collapse on top of him due to the magnetic pull, she decides that she must let go to save him. She tells him she loves him before letting go of his hand. Sawyer is beyond devastated, sobbing at his loss. After the bomb detonates, Juliet and Sawyer flash to a time when the Swan has been built, and similarly detonated. At first vowing to kill Jack over his loss, Sawyer recovers Juliet moments before she dies, and they share a final kiss. Her last words were, "it worked"
Since Then: The two shared Lost's first kiss in a scene where Sawyer demands a kiss in order to tell her where Shannon's inhalers are. She nurtured him through illness and the two bonded during many playful encounters. When both are captured by the Others, they bonded even more during their time working together in the rock quarry. During a beating while caged together on Hydra Island, Pickett demanded to know whether Kate loved Sawyer and under his threat to kill Sawyer she responded that she did. They made love in the cages. Sawyer's refusal to help rescue Jack created friction between them, but she went back to the Others for Jack, nonetheless. As Jack, Sayid, Hurley, Sawyer, and Kate leave the island on the chopper, Sawyer whispered something in Kate's ear, to her confusion. He kisses her and jumps off the chopper and into the ocean. Prior to the Oceanic 6's return to the island, Sawyer tells Horace that he had a "thing for this girl once", but after three years, can barely remember her face. However, upon seeing Kate, he is awash with nostalgia, but it is short-lived as he reminds a worried Juliet that "nothing's changed", and that he's with her [Juliet]. After a young Ben gets shot by Sayid, Kate and Sawyer attempt to save his life by bringing Ben to the Others. After Juliet's death, Sawyer leaves the main group, choosing to go at it alone. Kate, worried for his well-being, follows him back to the Barracks. She apologizes for Juliet's death, and starts to blame herself for the death by returning to the island.
Origin: Miles arrived at Sawyer's barracks, seeking to free Charlotte.
Since Then: Sawyer helped Kate to spring Miles and let him see Ben. When they left the barracks, Sawyer, Miles and Claire started towards the beach camp, and Sawyer issued a "restraining order" keeping Miles from Claire. They traveled back in time together, and the worked in DHARMA Initiative security as partners. They traveled to the future, and Miles helped Sawyer bury Juliet and read her last thoughts. They flew off the island together. In their afterlife, they imagined themselves as partners again, this time as Los Angeles cops. Miles there helped Sawyer get over his desires for revenge.
Origin: The two have despised each other since Kate and Sawyer's first day of work at the quarry.
Prize: Unknown. At this point, it is unclear why Pickett chose Sawyer. It may have been a case of hate at first sight, though Sawyer is not known to endear himself in these types of situations.
Fuel: Sawyer disarmed Pickett while working in the quarry, and tried to shock him with the taser ("Every Man for Himself"). Pickett saw Sawyer as a representative of the Losties after this, whom he blamed for the death of his wife ("The Cost of Living"). Pickett used Ben's surgery as a distraction to execute Sawyer, and only stopped when radioed that Jack was holding Ben hostage ("I Do"). When freed, Sawyer attacked him and caused him to be electrically shocked.
Origin: Sawyer approached Richard in 1974 and convinced him he was a time traveler.
Since Then: Sawyer became DHARMA's head of security, and he and Richard presumably met periodically over the next years. By 1977, they were on first name basis. Sawyer approached Richard with Ben Linus's body, and Richard agreed to heal him. Decades later, when Oceanic 815 crashed on the island, Richard helped prepare James's file and noted his search for the original Sawyer. He then handed this file to Locke, letting Sawyer kill Cooper. A few years later, after Jacob died, Richard approached Sawyer and frantically warned him against the Man in Black. The two escaped the island on a plane shortly after.
Origin: Racial tension quickly brought Sayid and Sawyer to violence, when Sawyer assumed that Sayid was responsible for the crash of Flight 815, based on stereotypes of Sayid's Iraqi background. Sayid, meanwhile, suspected Sawyer of being the fugitive after Sawyer found the marshal's badge and gun.
Prize: Machismo. For a short while, they also competed for Kate's attention, but Sayid chose Shannon instead.
Fuel: After Sayid was knocked out during the mission to triangulate the source of the transmission, Locke convinced him that Sawyer was the most likely suspect. Later, when the Losties assumed that Sawyer was withholding Shannon's asthma medication, Sayid and Jack attacked Sawyer in his sleep. They tied him to a tree, and shoved bamboo splinters underneath his fingernails, but he refused to talk. It turned out that he never had the medication. Disturbed by his own actions, Sayid left the camp on a solo mission to chart the Island. Sawyer maintained Sayid's signal fire in his absence, and when the man returned from Danielle's camp wounded, Sawyer noted an opportunity for revenge but did not take it.
Resolved: The two achieved mutual respect following this reconciliation, and in the season finale, Sawyer spoke highly of Sayid's technical skill, contrasting with his skepticism in the pilot. When Michael excluded Sayid from the expedition to retrieve Walt, Sawyer fought to include him and armed him with a gun. Later, they worked together in interrogating Juliet, who considered them one another's equals. Long afterward, a new conflict arose when Sayid entered James's town as a prisoner, and the two relived this dynamic in their flash sideways.