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What the Fathers say
Eastern Fathers
John Chrysostom
What then, saith one, is the head of virtue? Humility. Wherefore Christ also begins with it, saying, "Blessed are the poor." This head hath not locks and ringlets, but beauty, such as to gain God's favor. For, "Unto whom shall I look," saith He, "but unto him that is meek and humble, and trembleth at my words?" And, "Mine eyes are upon the meek of the earth." And, "The Lord is nigh unto them that are of a contrite heart." This head, instead of locks, and flowing hair, bears sacrifices acceptable to God. …
Theophylact of Ohrid
Blessed are the poor in spirit, for theirs is the kingdom of heaven. First He lays down humility as a foundation. Since Adam fell through pride, Christ raises us up by humility; for Adam had aspired to become God. The "poor in spirit" are those whose pride is crushed and who are contrite in soul.
Desert Fathers
John of the Thebaid said, 'Above all a monk should be humble. For this is the Saviour's first commandment, "Blessed are the poor in spirit, for theirs is the kingdom of heaven" (Matt. 5:3).'
Western Saints
Augustine of Hippo
The chief good is the only motive of philosophical enquiry; but whatever confers blessedness, that is the chief good; therefore He begins, Blessed are the poor in spirit. (Id. de Serm. in Mont. i. 1.) Augmentation of 'spirit' generally implies insolence and pride. …
Ambrose of Milan
In the eye of Heaven blessedness begins there where misery begins in human estimation.
Jerome
Blessed are the poor in spirit, for theirs is the kingdom of heaven. This is what we read elsewhere: And the humble in spirit will be saved (Psalm 34:16): But lest anyone should think that poverty, which is sometimes borne out of necessity, is being preached by the Lord, he added 'in spirit,' so that you would understand it as humility, not as lack. Blessed are the poor in spirit, who are poor by choice for the sake of the Holy Spirit. …
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