“‘Blessed are the poor in spirit: for theirs is
the Kingdom of heaven’ (Matt. 5:3).
It is indeed blessed to mark how [The Sermon on the Mount] opens. Christ began not by pronouncing maledictions on the wicked, but by pronouncing benedictions on His people. How like Him was this, to whom judgment is a strange work (Isa. 28:21, 22; cf. John 1:17). But how strange is the next word: ‘blessed’ or ‘happy’ are the poor—‘the poor in spirit.’ Who, previously, had ever regarded them as the blessed ones of earth? And who, outside believers, does so today? And how these opening words strike the keynote of all Christ’s subsequent teaching: it is not what a man does but what he is that is most important.
‘Blessed are the poor in spirit.’ What is poverty of spirit? It is the opposite of that haughty, self assertive, and self-sufficient disposition that the world so much admires and praises. It is the very reverse of that independent and defiant attitude that refuses to bow to God, that determines to brave things out, and that says with Pharaoh, ‘Who is the Lord, that I should obey His voice?’ (Exod. 5:2).
To be poor in spirit is to realize that I have nothing, am nothing, and can do nothing, and have need of all things. Poverty of spirit is evident in a person when he is brought into the dust before God to acknowledge his utter helplessness. It is the first experiential evidence of a Divine work of grace within the soul, and corresponds to the initial awakening of the prodigal in the far country when he ‘began to be in want’ (Luke 15:14).”
-A.W. Pink, The Beatitudes and the Lord’s Prayer, 15-16.