These precious words of Jesus’ second beatitude—“Blessed are those who mourn, for they shall be comforted” (Matt. 5:4)—are delivered against the backdrop of Isaiah 61. The prophet anticipates an age in which God’s Suffering Servant would bring comfort to God’s exiled people: “The Spirit of the Lord God is upon me, because the Lord has anointed me to ... comfort all who mourn” (Isa. 61:1–2; see also 40:1).
Seven centuries later, Isaiah’s promise crystallized into reality as a day laborer from Nazareth unfolded a scroll and launched His public ministry (Luke 4:14–21).
In the first beatitude, Jesus blesses “the poor in spirit” (Matt. 5:3)—those who acknowledge their moral bankruptcy. He then elaborates further, since it’s possible to acknowledge moral bankruptcy (v. 3) without mourning it (v. 4).
Counterintuitive and Countercultural
Given the human condition, Jesus’ promise to comfort those who mourn sin could scarcely be more counterintuitive. Given the spirit of our age, it could scarcely be more countercultural.
Sin in the late-modern West is not grieved. It’s not disapproved of. It’s not merely tolerated. It is celebrated. Our society doesn’t mourn sin; it mourns those who mourn sin.
Yet we can succumb to similar tendencies, can’t we? No doubt one reason we fail to mourn sin is because we underestimate it. We assume it’s little more than a cosmic parking ticket. But sin is not trivial; it is treason, an insurrection against heaven's throne. We have never committed a small sin because we have never offended a small God.
To the degree that we mourn our sin—both individually (Ps. 51:1–4; Luke 18:13; 1 John 1:9) and collectively (Ezra 9:4; Ps. 119:136; James 5:16)—we avail ourselves of heaven’s comfort. To the degree that we don’t, we rob ourselves of it.
Imagine awaking on the Fourth of July to a text from a friend: “Meet me for fireworks at 11 a.m.” You’d think it was a typo. Why? Because fireworks aren’t impressive in the noonday sky. The darker the sky, in fact, the more stunning the display. In the same way, the brilliance of grace must be set against the blackness of sin. As the Puritan Thomas Watson said, “Till sin be bitter, Christ will not be sweet.”
For the world, grieving sin is regressive and constricting; for the Christian, it is the pathway to joy. Imagine the implications. If Matthew 5:4 is true—if Jesus really meets repentance with comfort, not condemnation—then no longer do you need to fear being exposed. No longer do you have to present an airbrushed version of yourself to fellow redeemed sinners. No longer do you need to fear studying your heart and plumbing the depths of your disease. If exploring sin brings you to the deep end of the pool, exploring mercy will take you to the Mariana Trench. And awaiting you at the bottom of the dive is not a black hole but a solid rock.
In the final analysis, the Sermon on the Mount cannot be separated from its speaker. Jesus prayed many prayers during His incarnation, but never once did He pray a prayer of confession. He didn’t have to. He mourned over many sins, but never once did He mourn over His own. He didn’t have any.
Ultimately, our comfort is anchored in the reality that Jesus doesn’t just mourn sin; He conquers it. He invites us into this moral vision—this upside-down kingdom—and then dies in our place so we can enter it.
May God make our hearts tender to mourn our moral bankruptcy so that we can better marvel at His comforting grace.