Matthew 5:4

“Blessed are those who mourn, for they will be comforted.”

When Michael Jackson died on June 25th, 2009, the world paused. Everywhere I turned, people were crying, his music was playing, and tributes poured out—even in the church I was attending at the time. His funeral was watched by over 2.5 billion people, second only to Princess Diana’s. Michael Jackson, the “King of Pop,” had touched the world deeply.

But here’s the question: does Jesus mean that those 2.5 billion mourners were “blessed” just because they were grieving?

At first glance, this Beatitude seems strange. As John Stott once said, it could almost read: “Happy are the unhappy.”

What Does “Blessed” Mean?

In Scripture, “blessed” carries a rich meaning:

  • Approved by God.

  • Happy or fortunate (not by chance, but under divine favor).

  • Congratulated.

  • Covered with the anointing of the Holy Spirit.

So why would Jesus congratulate the mourner? Why would He call grief a blessing?

The Meaning of Mourning

The Greek word Jesus uses is pentheo, meaning deep sorrow or grief of the heart, often expressed through tears. Yes, this can apply to death, but Jesus is pointing deeper—toward the spiritual reality of His kingdom.

The mourning He speaks of is not just grief over loss, but grief over sin. It is the sorrow that comes when we realize we have wronged a holy God.

Think of Isaiah’s vision in Isaiah 6. When he saw the Lord high and lifted up, His glory filling the temple, Isaiah cried:

“Woe to me! I am ruined! For I am a man of unclean lips, and I live among a people of unclean lips, and my eyes have seen the King, the Lord Almighty.” (Isaiah 6:5)

Isaiah was “blessed” because in that moment, his sin was exposed and he mourned it. This is the kind of mourning Jesus calls blessed.

Mourning in Trials

James 1:2 tells us: “Consider it pure joy, my brothers and sisters, whenever you face trials of many kinds.”

Trials expose us. They surface what’s really in our hearts. Some suffering produces only complaining—what R.T. Kendall calls “ineffectual suffering.” But when we dignify trials by submitting to God in them, we experience “effectual suffering.” That kind of mourning leads to repentance, humility, and deeper dependence on God.

I had to face this recently myself. A client wasn’t paying me as agreed, and I was ready to let him have a piece of my mind. But the Spirit convicted me mid-call. I realized my anger wasn’t about justice—it was pride, frustration, and a desire to control. In that moment, God exposed sin in me. I sat in my car and mourned—not over finances, but over my pride. That mourning was a blessing, because it led to repentance and renewal.

Two Kinds of Suffering That Lead to Mourning

  1. When we suffer for doing right.

    • “If you are insulted because of the name of Christ, you are blessed.” (1 Peter 4:14)

    • Joseph was imprisoned for rejecting Potiphar’s wife (Genesis 39).

    • “It is commendable if someone bears up under the pain of unjust suffering because they are conscious of God.” (1 Peter 2:19)

    Sometimes suffering for righteousness makes us question: “Why me? Why now?” But Scripture reminds us, “We are destined for these trials” (1 Thessalonians 3:3). With suffering comes anointing.

  2. When we suffer for doing wrong.

    God also allows consequences to bring conviction. Hebrews 12:11 reminds us that discipline is painful, but it produces “a harvest of righteousness and peace for those trained by it.”

Whether through righteous suffering or corrective suffering, mourning over sin draws us back to the heart of God.

The Promise of Comfort

Jesus doesn’t just say, “Blessed are those who mourn.” He gives a promise: “for they will be comforted.”

The word comforted is tied to Parakletos—the name Jesus gave the Holy Spirit, our Comforter. When we mourn, the Spirit Himself comes alongside us:

  • To guide.

  • To counsel.

  • To strengthen.

  • To assure us of God’s love.

Paul reminds us:

“We are hard pressed on every side, but not crushed; perplexed, but not in despair; persecuted, but not abandoned; struck down, but not destroyed.” (2 Corinthians 4:8–9)

Outwardly, we may be wasting away, but inwardly we are being renewed day by day. Mourning is not the end. Comfort is coming. Hope is coming. Renewal is coming.

Reflection

  • Where is God exposing sin in your heart that requires mourning?

  • Are you allowing trials to make you bitter, or are you dignifying them and letting God shape you through them?

  • Do you believe that the Holy Spirit is your Comforter, even in your lowest moments?

Prayer:

Lord, teach me to see blessing even in my mourning. When you expose sin in me, give me the humility to repent. When trials come, help me to embrace them with joy, knowing You are working something greater in me. Thank You for the promise of Your Spirit, my Comforter, who renews me day by day. Amen.