Dr. Grace Devlin (Jordana Spiro) is a promising young surgeon working in Chicago's most pre-eminent hospital. Still, she can't escape her Southside roots. With her kid brother facing a mobster's wrath, Grace makes a deal and agrees to work off book for the infamous Chicago Outfit. As Grace's day job forces her to take on emotionally compelling cases; a convict determined to donate his heart to his estranged daughter, a whole family injured in a horrific hit-and-run; she is also forced to deal with mob-related tasks, doing emergency medical procedures in back rooms, treating mobsters hiding from the law and even working on a stolen thoroughbred only hours before he's due to race. Through it all, Grace fights to keep her dual life a secret... except from the one man who knows Grace best, Southside mob boss Constantine Alexander (William Forsythe), whose relationship with Grace is more than it seems.