Blessed Are The Upside-Down Series

Sermon Title: Blessed Are the Upside-Down

Series Title: Kingdom Culture: Living the Sermon on the Mount

Text: Matthew 5:1–12

Big Idea: Jesus opens His Kingdom manifesto not with rules but with congratulations. He blesses the weak, the weeping, and the overlooked. These “blessings” are grace-filled announcements that reorient how we see God, ourselves, and the world. The first of these blessings is the foundation upon which all the others rest.

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I. Introduction: Everything I Needed to Know...

There’s a charming little book by Robert Fulghum called Everything I Need to Know I Learned in Kindergarten. It’s filled with simple lessons like:

• Share everything.

• Play fair.

• Don’t hit people.

• Put things back where you found them.

• Clean up your own mess.

It’s not a theology book, but it makes a point: the most foundational truths often come early in life—and they stick.

For me, those lessons didn’t just come in kindergarten.

They came in Sunday School.

I grew up learning what it meant to follow Jesus from faithful Sunday School teachers. I remember the Beatitudes being a big part of that. At one point, they even used bees as a teaching tool—there were cartoon bees on the wall with phrases like “Be merciful,” “Be pure in heart,” “Be a peacemaker.” It was cute and memorable. But it was also deeply formative.

And then there was that classic song:

“The wise man built his house upon the rock…”

We sang it with hand motions and joy. And I didn’t realize it then, but that song was teaching me something profound. That song was the conclusion to the very sermon we’re beginning to study today.

Jesus’s most famous sermon—The Sermon on the Mount—begins with blessing and ends with a picture of a life that lasts.

These are the bookends of Kingdom living.

And in between them, Jesus gives us the vision for a new kind of humanity.

What He’s doing in the Beatitudes is not giving us a checklist or a self-help guide. He’s announcing something. He’s inviting us into a kingdom culture—one that runs counter to the world but produces a life that can stand the storms.

These opening verses—Matthew 5:1–12—show us that inner attitudes, not outer appearances, are the cornerstone of a life that stands the test of time. And the cornerstone of those inner attitudes is found in verse 3: “Blessed are the poor in spirit, for theirs is the kingdom of heaven.”

Just like I had to learn the Greek alphabet in Bible school—those basic letters became the building blocks for deeper study later on—we must return to this foundational truth. Without humility and spiritual poverty, we can go no further in Kingdom living.

Vince Lombardi, the legendary football coach, once held up a football to his professional team and began his training camp with these words: “Gentlemen, this is a football.” Even the most advanced players need to return to the basics.

Likewise, Jesus starts with the spiritual ABCs of the Christian life: poverty of spirit. Before we can do anything for God, we must admit our deep need for Him.

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II. What Is a Beatitude?

The word “beatitude” comes from the Latin beatus, meaning blessed, happy, or flourishing. In the original Greek, the word used is makarios – a word that describes the kind of joy that is rooted in God’s approval, not earthly circumstances.

So the Beatitudes are not commands. They are congratulatory proclamations from Jesus. As Lloyd John Ogilvie puts it, they are announcements of divine favor upon unlikely people.

Jesus is saying, “Blessed are you…” to those the world overlooks or oppresses. These blessings describe the character and conditions of those who belong to God’s Kingdom.

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III. The Setting (Matthew 5:1–2)

“Seeing the crowds, he went up on the mountain, and when he sat down, his disciples came to him. And he opened his mouth and taught them, saying…”

The setting is symbolic. Jesus goes up on the mountain, like a new Moses. But unlike Moses who received the Law from God, Jesus is God—speaking His authoritative Word.

He sits down, as rabbis did when giving formal teaching. This is not casual advice. This is a Kingdom constitution.

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IV. Verse-by-Verse: The Beatitudes (Matthew 5:3–12)

1. Blessed are the poor in spirit, for theirs is the kingdom of heaven.

“The word ‘blessed’ refers to the well-being of those who, because of their relationship to Christ and His Word, receive God’s kingdom, which includes His love, care, salvation, and daily presence… There are certain requirements if we wish to receive the blessings of God’s kingdom; we must be guided by the ways and values of God revealed in Scripture and not by the ways and values of the world. The first requirement is to be ‘poor in spirit.’ We must recognize that we are not spiritually self-sufficient; we need the Holy Spirit’s life, power, and sustaining grace in order to inherit the kingdom of God.” (Donald C. Stamps).