James "Sawyer" Ford is the man. He has a nickname for everybody and a laid back attitude. We learn that a con artist named Sawyer (later revealed to be Locke's father) conned James Ford's mother and father when the future Sawyer was just a boy. This then led to Mr. Ford killing his wife and then himself. A young James Ford saw the whole thing. He dedicated his life to finding and killing Sawyer, but ended up becoming a con artist himself and adopting the name Sawyer.
In "The Long Con," Sawyer pulls off the best con on the island, gaining control of all the weapons and medicine. He states, "there's a new sheriff in town."
Only 3 seasons later (and technically, 30 years earlier), Sawyer finds himself on a Dharma-controlled Island and adopts the alias James LaFleur. He becomes Head of Security. A position, ironically, that has a sheriff's star as its logo. Sawyer, as LaFleur, becomes the man he was meant to become.
Episode 2.13 The Long Con
Episode 5.08 LaFleur