Season 1, 08, Confidence Man: The con works out, but when Sawyer saw that the family had a little kid he walked away, it reminded him of himself. Season 2, 12, The Long Con: He tries to con Cassidy, who finds out. They start a relation ship, conning people together. Then Sawyer get's blackmailed and steals the money from Cassidy anyway. This time he get's caught and ends up in jail, which we find out in Season 3, 04, Every Man for Himself. Later in the series we find out that she was pregnant from him.