Sumner Redstone was one of the most important figures in the evolution of the media industry during the twentieth century. He saw opportunities and seized them, exponentially growing his father’s drive-in theater business to become one of the world’s largest media conglomerates, with two publicly traded companies—CBS and Viacom—at its core. His larger-than-life personality and trials and tribulations kept the tabloid press more than busy. But Sumner’s story was never his alone. Despite his megalomaniacal desire to take all the credit himself, his story is inextricably entwined with that of his family. This case study highlights the evolution of this complex family enterprise over several generations.