Andrew Cadoret, a transplanted Virginian, finds himself homeless and wandering aimlessly in Las Vegas, Nevada, when his girlfriend, Sarah, tosses him out on the street. Enter Connor, "Con-Man" Bentley, a seasoned professional gambler whose life Andrew saves and who is initially fascinated by the young man he dubs "Summerlin." Connor owes his allegiance to no one, but decides to take the lost Andrew under his wing, teaching him valuable life lessons in love, business, and how to not give a damn when the occasion warrants it. Along the way, both learn the value of this most unlikely friendship. Andrew's life at Connor's place-A casino-becomes filled with zany friends, hacky-sacking musicians and a gauntlet of Connor's "tests," which his mentor assures him "will only make him stronger." In following a rambling man, Andrew will risk his time, livelihood, and sanity. The lost love of Andrew's life, Sarah, learns a few life lessons of her own from the "Con-Man." Will Sarah and Andrew find a way to repair their relationship and fulfill the plans they had so carefully made? You can't win in life without a wager.