The aim of the article is to show the specificity of the fundamental fight in the soul and in the life of man between pride and humility as it is seen in the writings of the Cappadocian Fathers and John Chrysostom. In the opinion of the Greek Fathers of the 4th century pride is the root of all sin. It destroys all good fruits in the Christian spiritual development, whereas humility enables and protects spiritual growth. Arguing against the heretics of their time, mainly against the Arians, the Cappadocian Fathers (especially Gregory of Nazianzus) made particular attention to the theologians’ pride, characterized by the lack of respect for the mysteries of God and being proud that is without moderation in talking about God. Gregory of Nyssa pointed out the perversity of the vice of pride: the arbitrary exaltation leads finally to the great unwanted humiliation and even to fall into the sin. John Chrysostom emphasized the paradoxical risk characteristic of the process of spiritual fight: one can brag because of owned humility and enjoy it. Then even true humility can imperceptibly transform into pride and become its source. Therefore the righteous people should avoid the pride and seek humility with more care than sinners.