this is a recap of the flashbacks from season 2 (form tv.com). Note that while we see the flashbacks here, Sawyer was pinning Jack against Locke to get control of the guns. I feel it's worth to note that Sawyer betrayed someone he was in love with for his own self-interest:
The Long Con
In FLASHBACK we see Sawyer in a now familiar scene. He's in bed with a beautiful woman when he has to rush out to make a meeting. He grabs his briefcase and -- oops! -- thick bundles of cash "accidentally" fall to the floor. Only this time, his mark is on to him. But there's a surprise. Cassidy doesn't call the cops -- she doesn't even storm out of the room. Instead she wants him to teach her everything he knows.
In FLASHBACK we see Sawyer grooming his new pupil in the art of the con. Cassidy's a very bright pupil. But she's hungry for more. She wants to learn the long con. And she knows how they can fund it. Cassidy got more money than we thought in her divorce. A whole lot more: $600 grand.
In FLASHBACK we see Sawyer meet up with his old mentor, Gordie. They meet at the diner where Kate's mother is a waitress. He's been playing Cassidy like a fiddle, knowing the whole time there was more money in her. But when Sawyer says he's having second thoughts Gordie makes the decision real easy for him. Finish the job or, die. Turns out everybody works for someone…
Sawyer: (Cassidy just told him she has 600 grand) Well hell baby,
with that kind of money let's just sit out on some beach and drink
mojitos 'til we go toes up.
Cassidy: Sawyer, for the first time in my life I'm actually happy.
Come on, one long con? Then the mojitos.
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