The death of two siblings (Spencer Jones and Kiersten Lief) leaves a homeless man named Sonny (Joshua Greenberg) with a Cadillac to add to the modest fortune of cash he trudges around in a duffel bag, symbolic of the life he'd prefer to live without. When his sister Jesse (Sara Gross) drops in for a try at his bounty, he takes her on a hunt-to-nowhere for his own amusement, until finally giving her what she wants. The episode leads Sonny to suicide. But before he can pull the trigger, banging from the Cadillac's trunk stops him in time to save Mason (Jason Beck), the man inside. Mason leaves with the car that had once belonged to him and Sonny's journal, a life long confessional. When Mason's brother Clay (Alan Relkin) decides to read the book aloud, a cloud of judgment settles over Mason and turns his thoughts inward on his own shortcomings and regret.