Soren Kierkegaard, the nineteenth-century poetic philosopher, wrote about the encounter with the gospel in a way unmatched in the modern era. He perceived “the possibility of offense” in Jesus’ invitation: “The Halt—Come here now, all you who labor and are burdened, if you suffer most miserably, to be helped into even greater misery!” So, the burdened disciples come to Jesus as the Savior of their nation only to encounter his command to “take up their own Roman cross to follow him.” They are “helped into even greater misery.” In despair, they say, “Then who can be saved?” Meanwhile, Jesus’ compassionate healings of the needy provokes the religious leaders’ plot to destroy him to preserve their unjust societal power over the crowd. When Jesus’ execution is imminent, his disciples are stripped of all pretenses of following him. In the end, Jesus’ death and resurrection “ransoms” them. But why does their faith-trial occupy so much of Mark’s Gospel? Kierkegaard’s insights on spiritual despair, difficult faith, and crowd conformity reveal why humble self-knowledge before God prepares a person to fully receive Jesus’ “radical cure,” the gospel of the cross. This enables them to truly love God, themselves, and others.