There’s a temptation to think of poverty of spirit as a kind of timidity or small-spiritedness. There’s a temptation to think of the poor in spirit as a bunch of wimp-chickens. “Blessed are those you can hardly hear when they talk.” You’d be surprised how many people implicitly believe holiness has something to do with how loudly one speaks.
The poor in spirit are the broken of this world. Yes, they are the materially poor, the beggars, the laid off. But they are also the cast down. The anxious and the addicted. They are the heartbroken and alienated. They are the ones whose families have been taken away from them, “Rachel weeping for her children because they are no more” (Jer 31:15). The depressed. The seriously ill. Forgotten and beaten children. Les miserables. The poor in spirit are those who know nothing of this world’s joys. And painfully ― absurdly even ― Jesus says that they are blessed.
This is precisely what makes Jesus a shocking and radical figure. Recall that, when he finished this sermon, the text says “the crowds were alarmed at his teaching” (Mt 7:28). How is it that the world’s most broken can actually be blessed and fortunate?
Let’s exclude one solution straight away. There’s a temptation to think that, when God looks upon these poor in spirit and sees their misery, he will someday in this life wipe it all away and bless them. “Blessed are the poor in spirit because God will eventually dissolve their troubles and give them more than anyone else.” This is not what Jesus is saying. In fact, the Greek word he uses for “blessed” ― makarios ― implies that they are blessed because they are poor in spirit. Indeed, the poverty of spirit itself is somehow paradoxically blessed. It is precisely the place in which, to use Jesus’ words, one inherits the Kingdom of Heaven. There is no getting around the radicalness of Jesus. 
So what are we supposed to do with this? How is it that earthly misery is actually a blessing? How is it the place in which one inherits the Kingdom?
In short, when we are poor in spirit, we have nothing. When we are poor in spirit, we possess not a single one of this world’s joys. And so we must turn to the next world. We must turn to God. But most of the time ― for you and I, anyway ― we are not poor in spirit. Most of the time we enjoy the things of this world. We are happy to indulge its services. But the reason we are called blessed when we are poor in spirit is because it is only then that we actually see rightly. Indeed, when we are poor in spirit, that is the moment when it becomes all too clear that this world is devastated and broken and there is nothing that can save us except God. And that is a fundamental truth. And the reason this poverty of spirit is called blessed is because, at every other time ― when we are not poor in spirit ― we simply don't see it. The poor in spirit recognize that there is nothing in this world that can make one happy except God. But more often than not, we think that our jobs will make us truly happy. Or marriage. Or ice cream. Or not dying. Or some other thing besides God.
Recall for a moment the Parable of the Prodigal Son. Recall the elder son’s anger at seeing a party thrown for his brother. “These many years I have served you and I never disobeyed your command; yet you never gave me a goat, that I might make merry with my friends” (Lk 15:29). What he wanted was a goat. “Son,” the father replied, “you are always with me. All that is mine is yours” (Lk 15:31). The father is not talking about his possessions: “You are always with me.” The son wanted a goat. “Forget the goat,” the father is saying, “you have me.”
“Blessed are the poor in spirit,” Jesus said, “theirs is the Kingdom of Heaven.” In the Kingdom of Heaven, everyone is a beggar, because everyone has given everything away. They’ve recognized how unsatisfying everything is that isn't God. This is what it means to be rich for Christians. This is the inheritance of the Kingdom of Heaven. This is what it means, as Saint Paul said, to “have nothing, and yet possess everything” (2 Cor. 6:10). And once one becomes poor of human things, one becomes rich with God. In the Kingdom, everyone has given away their goats. They have the Father. “Son. Daughter. You are always with me. And all that is mine is yours.”
~Anthony Rosselli (PhD cand., theology, University of Dayton) writes out of St. Luke and Ascension Parishes in Franklin County, Vermont. These columns are archived here.
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 See Erasmo Leiva-Merikakis, Fire of Mercy ― Heart of the Word: Meditations on the Gospel According to Saint Matthew, vol. 1 (San Francisco: Ignatius Press, 1996), 183-184.