This study explored the role of the first Beatitude—“blessed are the poor in spirit”—in the practice of leadership by those who lead by the Beatitudes. Two participants, a community college president from North Carolina and a Methodist minister from the Bahamas who practice leadership by the Beatitudes, were chosen, and an indepth examination of their leadership concepts and everyday application was investigated. Two case studies were conducted through interviews and observations, and three followers for each leader were interviewed. Both leaders and followers exhibited that the first Beatitude is pivotal in the practice of the other Beatitudes and that it is the foundation of the practice of kinder and gentler leadership. Humility is a crucial ingredient in beatific leadership. The findings further support Winston's (2002) speculation that the Beatitudes are hierarchial in the practice of leadership. Other main issues relating to the first Beatitude are the six other Beatitudes in addition to related issues such as dependence on God, learningfulness, love for others, love for dialogue, self-effacing, resoluteness, and regarding mistakes as part of the learning process. Whereas some of these related issues are not Beatitudes in themselves, they are integral in the practice of beatific leadership. Both leaders also displayed superleadership tendencies in the training of other leaders as part of beatific leadership.