For ten-year-old Bentley Fair, life has not been so easy. He has lived in and out of foster homes, never trusting anyone but his older sister Grace. He longs to feel safe, a feeling that he has never known due to being haunted by a tall shadow for as long as he can remember. He has never even told Grace about the tall shadow. His only hope is that one day, he will find his forever home and finally believe that he is safe. Bentley and Grace now live at Mr. Boldmore's home for children. On Grace's 18th birthday, she and Bentley are shocked to discover that they have inherited an island, tower, and treasure map from their late mother. Grace suddenly leaves for the island, giving Bentley little clue why. He knows that it is up to him to follow the map and find her. Ms. Boldmore suggests that he wait until after the new parents' day. "What if your perfect parents will be there?" she says. Bentley doesn't like it, but he tries the 'what if' thought and finds that dads Will and Harry, though not what he expected, are truly a perfect fit for him. In his new home with Will and Harry, Bentley is happier than ever, and best of all, the tall shadow is nowhere to be found. He befriends the next door neighbor, the mysterious Mr. Flair, who just might know the way to help Bentley find his sister. Will he find Grace? Will the shadow return? Is Bentley's family ever going to be together? In this story, author/ illustrator Mary Truly hopes that Bentley's spirit of adventure will inspire readers to believe in themselves and try some 'what if' magic of their own.