One of the deepest and most complex characters of the LOST world, Josh Holloway’s character, Sawyer’s story.
When James Ford, was a young child, a man named Sawyer, a con artist, tricked his mother into giving all of their family’s savings to him. James then witnessed his father murder his mother and then pull the gun on himself while he was just inches away, under the bed. Young James then writes a letter:
“Dear Mr. Sawyer, You don’t know who I am but I know who you are and I know what you done. You had sex with my mother and then you stole my dad’s money all away. So he got angry and he killed my mother and then he killed himself, too. All I know is your name. But one of these days I’m going to find you and I’m going to give you this letter so you’ll remember what you done to me. You killed my parents, Mr. Sawyer.”
He then dedicates his life to finding the man responsible for ruining his life and causing his father’s incredible emotional distraught.
In the process of hunting Sawyer, he becomes him. Evolving into the very man he’s so desperately hunted. After waking up beside a beautiful woman, he gets up quickly, realizing he’s late for his meeting. After picking up his brief case, it spills open to reveal a ton of cash. After telling her she wasn’t supposed to see that, he then gets her to commit her and her husband’s money to “help” Sawyer make a big investment.
After letting her husband keep the money overnight, they finally agree to invest. Sawyer comes over to their house to make the final deal and is just about to leave when he sees a little boy, presumably their son. Immediately, he states that the deal is off. Unable to go through with the exact con the real Sawyer had made against him so many years before.
Some time later, he tries the exact same con, this time waking up beside another beautiful woman named Cassidy. She immediately recognizes the con, however, and, rather than whisking him out of her life, asks to join him. They go on to do a few small cons together, including one where they grab cheap necklaces and put huge price tags on them. “It’s not about the necklace,” Sawyer contends, “It’s about the price tag.”
After awhile, Cassidy asks Sawyer if she can get in on the “big stuff” like a big con. Sawyer explains to her that a long con is when you stay with someone a long time, implementing an idea and making them think that it’s their idea. When she says she wants in on something like that, Sawyer says they can’t do it without money. That’s when Cassidy reveals that she does in fact have six hundred grand stowed away that she didn’t tell him about. Little does she know that he knew it all along and she was the long con. After Sawyer tells Gordy in the restaurant that he got all six hundred grand, it is evident that he had actually fallen for the girl he was conning. Sawyer then tells him he can’t do it but Gordy threatens to kill him and Cassidy both if he doesn’t.
When Sawyer comes back to Cassidy’s house, he stuffs all her money in a duffle bag, telling her everything and to get out of there as soon as possible. After walking outside, he counts to five Mississippi and then walks back inside to retrieve another duffle bag holding her real money.
The next flashback Sawyer has is in jail. After beating up a guy in a boxing ring pretty bad, he meets a new prisoner named Munson. Apparently having ripped off the government for ten million dollars, Munson, though brand new, is already getting special treatment by the warden. Sawyer comes and warns Munson that the only reason the warden would do that is to get a shot at a little monetary recompense once Munson is released. Sawyer finally gains his trust and he asks him to move the money for him once he’s out.
In the midst of all this, Cassidy comes to visit him. After Sawyer corrects her about his name, “It’s James Ford,” she tells him that he has a daughter named Clementine. He denies it, declaring that he “ain’t got no daughter”, and storms out.
The next scene shows Sawyer is summoned into the warden’s office. After telling him the money is located in a red bronco, he’s set free. When asked what to do with his small part of the money, he asks them to set up an account in the name of Clementine Phillips and to make it to where Cassidy can’t figure out where it came from.
After an awkward encounter in a hotel involving another one of Sawyer’s pretty women, a man named Hibbs, who Sawyer said he would kill, claims to have found the original Mr. Sawyer from his childhood.
Hearing he’s in Australia, Ford gets there as soon as possible, (thus his reason for being on Flight 815 on the way back to the US). After purchasing a gun, he goes to the place where Hibbs told him that Sawyer was, a small little shrimp truck. After making friendly conversation, he finds himself unable to pull the gun up and takes off without a word.
He then ends up at a bar, taking shots. It turns out that Jack’s father, Dr. Christian Shephard, is in the same bar. He convinces him that they can’t do anything about fate, same reason the “Red Sox will never win the World Series”. Shephard then tells him that if his “business” will ease his suffering, then to get out and do it.
The next scene, we see Sawyer back at the shrimp truck in the rain. As the man takes the trash out, he yells, “Saywer,” and shoots him in cold blood. The man mutters, “Tell Hibbs I would’ve paid him,” and Sawyer realizes he’s shot the wrong man.
Sawyer then ends up in the Sydney police station, having apparently head-butted a man of high social status. After claiming his innocence, they say they have witnesses who say otherwise. The cop then slaps a plane ticket on the desk and tells him never to return to Australia, which leads him to Oceanic Flight 815.