After graduating from the University of Pennsylvania in 2004, Smiley earned his J.D. at Syracuse University College of Law, before practicing commercial litigation in New York City. From there he pursued a career in sportswriting.

His interest in sports (chief among them, football) and sports betting goes back to before he can remember, perhaps when he accompanied his father to an OTB parlor in the ’80s, later telling his first grade classmates that his father bet on horses for a living. Brett began playing fantasy football in the pre-internet loose-leaf paper era, and betting football games on the playground. At Penn, he played offensive guard on the Quakers’ Collegiate Sprint Football Team, earning a letter each season.

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