His daddy's recent and mysterious departure has left sixteen-year-old Billy Ray Jenkins with a deep well of anger and sadness. It grows evermore bottomless with the news that his momma, Jolene, chronically ill from injuries sustained in a long-ago accident, has only a short time left to live. With Jolene's death imminent, her sister, Becky, seeks to provide a home for Billy Ray and his young brother Jeb. But for all her good intentions, Aunt Becky, partially disabled, is a woman of even lesser means than Billy Ray's own struggling family. She also comes with a volatile, alcoholic husband, Roy, who for reasons unknown has it in for Billy Ray. Looking down the barrel of an uncertain future for himself and his brother, Billy Ray sets out to find their missing daddy, with whom he shared a close and loving relationship, only to jump off course when a startling deathbed confession from Momma leads him to question everything about his life, including his own identity.
In the wake of Jolene's death, while defending best friend Frankie against a school bully, Billy Ray suddenly finds himself at odds with local law enforcement. With his freedom threatened and his brother's future subsequently hanging in the balance, Billy Ray, struggling to imagine how he might redeem himself in the eyes of police, the administration, and even Aunt Becky, has never felt more alone. It's during this time that Billy Ray meets the incomparable Jenny, who helps Billy Ray discover his worth and his strength-that through pain and hardship, he has gained the wisdom and the courage to face his fears, rise to his better angels, and overcome the trials of life.
Set against the backdrop of one of America's most beautiful and historically rich cities, The Prettiest Street in Savannah is a story of great loss and renewal, of high stakes and devastating secrets, of unrelenting values in the face of adversity. At its heart a coming-of-age tale, the novel sets its sights on an unlikely hero, Billy Ray Jenkins, who works to secure a better future for himself and his brother, comes to acknowledge a number of hard truths about life, and discovers the power of true friends and family.