This study is caused by the argument of Wendy Meyer, who argues that to characterize Chrysostom as a “lover of the poor” is to misunderstand him against the argument of Peter Brown. She insists that it is more accurate to call him not “champion of the poor,” but “champion of the voluntary poverty.” But the author is not to focus on the contrast argument of above two scholars but to investigate their argument from view point of the monk-bishop leadership. Therefore, the purpose of this work is to present how the leadership of monk-bishop leadership is forming and figuring out. In fact, “the lover of voluntary poverty” and “the lover of the poor” seems to have the deep gap, which could not overcome. Nevertheless, the new leadership, which evolves above two strange factors, is emerging in the name of monk-bishop leadership in late Antiquity. By focussing on life, work and time of John Chrysostom, this investigation will, portray the transitions of how “the lover of voluntary poverty” and “the lover of the poor” are connecting. John Chrysostom (d.407) lived the monastic life for the several years in the mountain. And he was the presbyter and bishop of Antioch and the Bishop of Constantinople. He is very strong position. in its examination of late-antique poverty. He had an enduring influence on his communities with abundant references to the poor and/or almsgiving to be found in his 823 homilies, 242 letters and fourteen treatises. Particulary, in studying of church and state in late Antiquity, this work has great depts on the study of Peter Brown.