In The Winning Certificate, Sylvia Medina, a student at Central High joins a teenage gang after her adopted mother's death and is trapped in a life style of violence and hopelessness. Can the school's Literary Club and an image on the computer of her birth mother provide the hope necessary for Sylvia to survive?
Antonio Medina, after his wife's death from cancer tries everything to get Sylvia back on track. However, nothing helps until Rick Podowski and Leti Rios, advisors to the high school Literary Club, get Sylvia involved. Sylvia reluctantly shares some of her poems. Then, as Sylvia becomes more committed, she begins to change and becomes in touch with her feelings.
As Sylvia develops her ties to the Literary Club, she gets more intrigued by the picture of her birth mother and tries to find her. She learns that her mother lives in New York and when members of the Literary Club go to Columbia University to attend a conference and receive an award for their magazine, Sylvia goes along. Instead of going to the conference, she visits her mother.
She finds out that her mother married a very rich man, and she has two stepsons. The stepfather is dead, and the two sons along with her lawyer are trying to get her farm and include it as part of a land trust being used as a means to launder money for the mob. Murder, kidnapping, money laundering, and mob activities are included in this novel.