Blessed are the poor in spirit,
for theirs is the kingdom of heaven.
The beatitudes are obviously counterintuitive from a worldly perspective. Generally, if asked how to obtain kingdoms, comfort, land, or other rewards, we would guess that the easiest way would be through power and wealth. How might we receive mercy? Perhaps through emotional appeal or even deception. How might we see the vision of God? Perhaps through some exclusive calling, since Moses at least was allowed to see God's back, or through pursuing the secret knowledge of the Gnostics. How might we be regarded as children of God? Such a designation was typically reserved for kings and emperors. Normally persecution would be a hindrance to receiving a kingdom. But here it is part of the process according to the expected program. In this beginning of his Sermon on the Mount Jesus upends all of our intuitions about how to attain blessedness.
The beatitudes are counterintuitive for another reason as well. For disciples who have been formed in the Gospel of grace, and trained to recognize anything that reeks of Pelagian achievement through our effort, this program of Jesus for how to attain fulfillment at first seems a little too closely tied to the formula of first doing one thing to attain a result, as though we earned it. Where in this program is there room for God's grace? Yet perhaps it is there, beneath the surface, as an assumed prerequisite. One beatitude should suffice as an example.
Blessed are the merciful,
for they will be shown mercy.
This is reminiscent of the Our Father in which we pray to be forgiven because we forgive. But if we look at this in the larger context of the Gospel of Matthew we will also encounter the Parable of the Unforgiving Servant (see Matthew 18:21-35). In it, the servant did not earn the forgiveness of the master. It was wholly unearned and unmerited. It was only on this basis that he was judged on whether or not he would show mercy to others. In order to actually obtain and enjoy the mercy he had already received he had to be willing to show that same mercy to others. So too with us and this beatitude. It's not like the mercy we are able to show to others comes out of nowhere, or that it is generated by our moral striving. It is rather a result of the fact that we have already received mercy from God, that he in fact acted merciful toward us before we could do anything to deserve or even desire it.
If we are called to spiritual poverty it can only be because of Our Lord Jesus, "became poor, so that through his poverty you might become rich" (see Second Corinthians 8:9). The reason our mourning can lead to joy as because Jesus did not despise shedding tears for our sake for the joy that was set before him. He now allows our tears to share in the merit of his tears so that his joy may become our own.
The beatitudes, then, require grace to attain. They never give us boasting rights. We cannot brag about what great peacemakers we are, or the degree to which we have despised wealth, or even the purity of our hearts. Paul was clear on this point and we should be as well. All is gift. All is grace.
It is due to him that you are in Christ Jesus,
who became for us wisdom from God,
as well as righteousness, sanctification, and redemption,
so that, as it is written,
"Whoever boasts, should boast in the Lord."

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