The Beatitudes read like a list of sacred paradoxes. The Lord began His Sermon on the Mount with a series of seemingly incongruous promises. “Blessed are the poor in spirit, for theirs is the kingdom of heaven. Blessed are those who mourn, for they shall be comforted” (Matthew 5:3-4). Taken at face value, they don’t make sense.
But that apparent dissonance is by design, as Christ boldly confronted the assumptions of the world and the religious rhetoric of His day. As we saw last time, the point of Christ’s message was to prompt us to self-examination—to show us the true measure of faith by contrasting it against the emptiness of self-righteousness and legalism.
In short, He’s contrasting pharisaical works-righteousness with true spiritual righteousness. He’s not interested in the outer man until the inner man has been thoroughly dealt with. And that’s apparent from His first words.
The Poor in Spirit
Imagine how confusing these opening words must have been for Christ’s audience: “Blessed are the poor in spirit, for theirs is the kingdom of heaven” (Matthew 5:3). In his book The Only Way to Happiness, John MacArthur explains the curious and potentially off-putting way Christ begins His message:
Why does Christ begin with the poor in spirit? He’s talking about a new standard, a new way to live, so why begin here? What makes this the source of happiness? Well, because it is the fundamental characteristic of a Christian. Becoming poor in spirit is the very first thing that must happen in the life of anybody who ever enters God’s kingdom. Nobody ever entered on the basis of pride. The doorway is very low, and only people who crawl can come in. . . .
God gives grace to the humble. That’s why a poor spirit has to be at the very beginning. The only way to come to God is to confess unrighteousness, confess inability to meet God’s standards, confess that you can’t do it. You enter with a sense of helplessness and desperation to receive divine blessing, and you maintain that sense in order to know continual happiness as you live in Christ.  John MacArthur, The Only Way to Happiness (Chicago: Moody Publishers, 1998), 57-58.
Christ’s point is clear: A life of blessing and happiness starts with understanding the true wretchedness of your soul and your utter inability to do anything about it. Until we recognize the true poverty of our spiritual state—as long as we hold onto the notion that we can manufacture our own righteousness—there’s nothing God can do for us. The first step to accessing His blessing is to acknowledge you can do nothing for yourself.
Blessed are those whose spirit is destitute. Blessed are the spiritual paupers, the spiritually empty, the spiritually bankrupt who cringe in a corner and cry out to God for mercy. They are the happy ones. Why? Because they are the only ones who tap the real resource for happiness. They are the only ones who ever know God. Theirs is the kingdom—then and there, here and now.
This truth is not just in the Sermon on the Mount. James wrote, “Humble yourselves in the presence of the Lord, and He will exalt you” (4:10). This is not a poverty against which the will rebels, but rather it is a poverty under which the will bows in deep dependence and submission. This is a rather unpopular doctrine in the church today. We emphasize celebrities and experts and superstars and rich, famous Christians. But happiness is for the humble.  The Only Way to Happiness, 60.
Scripture repeatedly emphasizes the value of spiritual humility. “The Lord is near to the brokenhearted and saves those who are crushed in spirit” (Psalm 34:18). And Psalm 51:17 says, “The sacrifices of God are a broken spirit; a broken and a contrite heart, O God, You will not despise.”
The classic example is the confession of the publican in Luke 18:13, “But the tax collector . . . was even unwilling to lift up his eyes to heaven, but was beating his breast, saying, ‘God, be merciful to me, the sinner!’” As Christ explained, “Everyone who exalts himself will be humbled, but he who humbles himself will be exalted” (Luke 18:14).
The Lord makes a similar promise at the end of His first Beatitude: “Blessed are the poor in spirit, for theirs is the kingdom of heaven” (Matthew 5:3). John MacArthur explains what that glorious promise entails:
The kingdom, as I see it, is grace and glory. Grace now, glory later. We possess the kingdom. It is ours—the rule of Christ, the reign of Christ in our lives. Do you know what that means? We are His subjects; He takes care of us. He gives us what we need. He fulfills every need of our hearts. That’s the result of being poor in spirit.  The Only Way to Happiness, 66.
The poor spirit understands its limitations—it’s desperate for a redemption it cannot conjure on its own. And in God’s grace and mercy, it finds restoration, fulfillment, and favor in His eternal care.
Inward spiritual poverty has a natural outward extension, and Christ identifies it in His second Beatitude: “Blessed are those who mourn, for they shall be comforted” (Matthew 5:4).
We must not take that as a blanket blessing for anyone who ever mourns about anything. Christ is not referring to general sorrow—the normal weeping and mourning that accompany loss and heartache common to every man. Nor is he talking about petulant sorrow—the selfish kind of sadness attached to not getting our way.
Instead, as John MacArthur explains, Christ has in mind here a specific kind of godly mourning:
The apostle Paul helps us understand this sorrow in 2 Corinthians 7:10, “For the sorrow that is according to the will of God produces a repentance without regret, leading to salvation, but the sorrow of the world produces death.” You can cry your eyes out about your problems, and you can weep all you want about loneliness and about discouragement and about disappointment and out of earnest love. . . . When it’s all said and done, none of that worldly sorrow will bring you life.
Only one kind of sorrow brings life, and that is godly sorrow, which leads you to repentance. Therefore, we can conclude that Jesus is referring in this Beatitude to sorrow over sin. . . . Godly sorrow is linked to repentance, and repentance is linked to sin. This kind of mourning means being sorry because you’re a sinner.
The Beatitudes began by referring to spiritual bankruptcy and knowing it. That is the intellectual part. Verse 4 is the emotional part. Because you know you are spiritually bankrupt, your emotion takes over, and you mourn that bankruptcy. Such are kingdom people. Poor in spirit is a recognition that we have nothing and that we are nothing and that we can do nothing, and it results in our being a beggar who has no resource, no capacity to help himself.  The Only Way to Happiness, 76-77.
Put simply, Christ promises to bless those who are truly grieved over their sin. What He’s describing here is an essential element in repentance. There is no salvation apart from repentance, and no repentance apart from grief over the presence and power of sin in our lives.
Moreover, this is not a temporary sorrow—we’re not sorry we were caught sinning, but truly grieved over our nature as sinners. God’s people loathe the corruption of sin, and long to be free of its influence. As John explains, “Conviction of sin must precede and follow conversion.”  The Only Way to Happiness, 81. He writes,
There’s no greater message I can think of for the church today than for it to start crying instead of laughing. It grieves my heart to see the frivolity and the foolishness that goes on in the name of Christianity. Nobody ever came into the kingdom of God who did not mourn over his own sinfulness. You cannot verify that you are a true Christian unless throughout your life there is the same sense of grief over the sin in your life.  The Only Way to Happiness, 80.
If you don’t take your sin seriously—if it doesn’t grieve you to your core—then you have good reason to doubt the authenticity of your faith. There’s no assurance for those who take an apathetic, indifferent, or lackadaisical view of sin. And as that attitude permeates the church, God’s people lose their ability to be salt and light to a world still caught in sin’s clutches.
If we want to be blessed—or see others blessed—we need to heed Christ’s words in Matthew 5:4. He didn’t offer comfort to those who were vaguely bummed or temporarily disappointed about their sin. As John MacArthur explains, the Lord only promised comfort to those who first mourned their sin.
The emphatic pronoun autoi is used here, which emphasizes “blessed are they who continue to mourn, for they alone shall be comforted.” Only the mourners know the comfort of God. Only those who mourn their sin know what it is to have their tears dried by the loving hand of Jesus Christ.  The Only Way to Happiness, 84.
The path to God’s blessing begins with a right view of your sinfulness and spiritual bankruptcy. That’s the promise of the first two Beatitudes—a promise echoed in James 4:10, “Humble yourselves in the presence of the Lord, and He will exalt you.”