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- Conning yet another female who'd be getting a financial windfall from a divorce settlement. This would be particularly poignant if the flashback to this played out as Jack and Sawyer get closer to competing for Kate's affections, as the producers hinted they would in their final Podcast to Season 2.
- Also as they are seeming to become closer to one another. Nearing the end of season 2, Sawyer tells Jack 'You're the closest thing I have to a friend'. Also the situation with them being held by the Others will no doubt bring them closer.
- Since we have seen that Sawyer always scopes out the husband of the woman he is trying to con, this would mean that Sawyer knew Jack (or at least knew of him) before the crash. However, he has never displayed any sign of this.
- Bringing Jack, Sawyer and Kate to the Hydra Island was a test to see if history would repeat itself. It did - Sawyer stole Jack's girl once again.
- Would explain why he called Ana Lucia 'Sarah'.
Kevin, her ex-fiance
- Possibly turned to Kevin when her marriage fell apart.
Bryan, Shannon's ex-boyfriend
- Has a striking resemblance to Shannon's boyfriend in Australia, a known con-man.
- Admits to having a relationship with an unnamed American woman.
- This theory would suggest that Sarah, like Lee, went to Harvard.
See Also: Jae Lee's American woman
- The man waiting for Sarah at the end of Jack's flashback in "A Tale of Two Cities" bears a strong resemblance to Pickett.
A previously unseen character
- There might also be two of them: refer to the picture in the infobox.
- Probably not either person in the info box. She was keeping her lover secret so it is unlikely that she would bring him along to get Jack out of jail.