Ryan Bingham's job is to fire people from theirs. The anguish, hostility, and despair of his "clients" has left him falsely compassionate, living out of a suitcase, and loving every second of it. When his boss hires arrogant young Natalie, she develops a method of video conferencing that will allow termination without ever leaving the office - essentially threatening the existence Ryan so cherishes. Determined to show the naive girl the error of her logic, Ryan takes her on one of his cross country firing expeditions, but as she starts to realize the disheartening realities of her profession, he begins to see the downfalls to his way of life.
It's 1954, and up-and-coming U.S. marshal Teddy Daniels is assigned to investigate the disappearance of a patient from Boston's Shutter Island Ashecliffe Hospital. He's been pushing for an assignment on the island for personal reasons, but before long he wonders whether he hasn't been brought there as part of a twisted plot by hospital doctors whose radical treatments range from unethical to illegal to downright sinister. Teddy's shrewd investigating skills soon provide a promising lead, but the hospital refuses him access to records he suspects would break the case wide open. As a hurricane cuts off communication with the mainland, more dangerous criminals "escape" in the confusion, and the puzzling, improbable clues multiply, Teddy begins to doubt everything - his memory, his partner, even his own sanity.