It is curious that the New Testament—arguably the most significant book in human history—begins with a genealogical record. Christianity introduces itself to the world with what may appear to be an uninteresting, even boring literary form. Often missed, however, are the provocative elements to Matthew’s record of Jesus’ ancestry. Not only is the mere mention of five women unusual, given the paternalistic subculture of ancient Israel, but the particular stories embedded in the genealogy cryptically provide color, drama, and even juicy scandal. These female portraits reveal both the depths of the human condition of brokenness, as well as the brilliance of the gospel as revealed in the ultimate descendant of these women.