Part 1 of “BLESSEDR: A Study of the Beatitudes”
September 20, 2026
Glynwood Baptist Church, Prattville, AL
James Jackson, Pastor
[title slide: Blessing Begins With Brokenness]
Good morning. Please open your Bibles to Matthew 5.
In the 1960s, states everywhere were looking for ways to generate more revenue. One state believed some of its citizens might be willing to pay extra money for the privilege of personalizing their license plates, rather than settling for the random tag number the DMV issued to them. And thus, the vanity plate was born. At last count, there were more than nine million vanity plates on American roads—about four percent of all registered vehicles.
Here’s a trivia question: Can you guess the first state to make vanity plates available?
That’s right. California.
I’m not saying there are more vain people in California. You can draw your own conclusions.
And to be honest, I’m grateful to them. Because decoding vanity plates is one of the only things that makes being stuck in traffic bearable.
Here are a few fun ones. This one belonged to the owner of a prominent nail salon in town:
TOES R US
Or how about this one?
9N3QTRZ
I’ll be honest— this one stumped me, until I noticed all the Harry Potter bumper stickers on the back of the car. One said “My other ride is a Nimbus 2000.
Now do you get it?
Here’s one that— well, I don’t even know what to say…
BLONDE [but mounted upside down]
Okay. Now that I’ve got you playing the game, I’ve got one more for you.
BLESSEDR [on the back of a Ferarri]
What does that say?
It’s hard to say, because you don’t know for sure what was going on in the owner’s head when they ordered that tag. Maybe its a doctor who’s last name is Blesse. [“Blesse Dr.”] Or maybe, since it’s on a Ferrari, the owner was saying, “Well, lots of people are blessed, but I’m blessed-er.”
But if you are familiar with the New Testament, specifically Jesus’ famous Sermon on the Mount, you might look at this and read,
Blessed Are…
And that’s where we are going with this new sermon series. Over the next 8 weeks, we are going to look at a passage of Scripture known as the Beatitudes.
Eight times, Jesus begins a statement with those two words:
Blessed are.
Blessed are the poor in spirit.
Blessed are those who mourn.
Blessed are the meek.
Blessed are those who hunger and thirst for righteousness.
And right away, you probably notice that Jesus’ list of blessed people is way different from what our list would be.
Because we tend to think more like our hypothetical Ferrari owner. There’s being blessed— having good health, a steady job, a strong marriage, normal kids.
And then there’s “blessed-er:” Not just healthy, but being a star athlete. Not just a steady job, but being rich. Not just having a good family, but having a 24 hour Facebook highlight reel of a family.
Those are the kind of people that would make our “Blessed are” list, right?
We naturally assume that being “blessed-er” means being healthy-er. Or wealthy-er. Or famous-er.
We start at the top of the mountain.
But Jesus starts at the bottom.
By the way, the Bible itself never calls this the sermon on the mount. Jesus didn’t sit down and say, this morning’s sermon is entitled The Sermon on the Mount.
One pastor has suggested we call it “The Sermon from the Monarch.” Because this isn’t simply good advice Jesus gave on a hillside. This is the King telling the citizens of His kingdom what life under His rule looks like.
And that matters, because Christians are pretty good at giving Jesus theological authority. We believe He is the Son of God. We believe He died for our sins and rose from the dead. We sing that He is King of kings and Lord of lords.
But if Jesus is Lord, His authority doesn’t stop with what we believe about Him. His authority extends to how we live because of Him. He gets to define what is good. He gets to define what is righteous. And He gets to define what it means to be blessed.
So for the next eight weeks, we’re going to put ourselves under the authority of Jesus and let the King tell us what the blessed life looks like.
If you are physically able, please stand for the reading of God’s Word. And since we are going to be in this passage for the next 8 weeks, I’m going to challenge you to memorize Matthew 5:1-12. And just to sweeten the deal, anytime in the next 8 weeks, if you can quote the Beatitudes to one of our ministers, you’ll get a sticker of our series logo. Sound like a deal? Awesome. Let’s read together. And I want you to read verses 3-10 out loud. Ready?
Read Matthew 5:1-12. With each Beatitude, advance the slides.
THE SETTING
Before we get to what Jesus said, I want us to picture where He said it, and more importantly who He said it to.
Matthew tells us at the end of chapter 4 that Jesus’ reputation was spreading rapidly. Look at those verses:
Matthew 4:23–25 ESV
23 And he went throughout all Galilee, teaching in their synagogues and proclaiming the gospel of the kingdom and healing every disease and every affliction among the people. 24 So his fame spread throughout all Syria, and they brought him all the sick, those afflicted with various diseases and pains, those oppressed by demons, those having seizures, and paralytics, and he healed them. 25 And great crowds followed him from Galilee and the Decapolis, and from Jerusalem and Judea, and from beyond the Jordan.
He was teaching in the synagogues. He was proclaiming “the gospel of the kingdom.” He was performing miracles. And the word about him was spreading.
Matthew says they came from Galilee and the Decapolis, from Jerusalem and Judea, and even from beyond the Jordan. People were coming from everywhere to see Jesus, to hear Jesus, and undoubtedly to figure out exactly who Jesus was.
And you have to remember what an electrically charged word kingdom would have been in first-century Israel.
These were people living under Roman occupation. They knew the promises God had made to David. They knew the prophets had spoken about a coming King and the restoration of God’s people. And especially in Galilee, there was a history of resistance to foreign rule. So when a Jewish teacher began traveling through Galilee announcing, “The kingdom of heaven is at hand,” people were going to pay attention.
What does He mean by kingdom?
Is this the One we’ve been waiting for?
Is God finally going to do something?
And with those questions hanging in the air, Matthew 5 begins:
“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.”
Notice that.
If you’ve ever been on a tour of Israel, you may have heard somebody stand on a hillside overlooking the Sea of Galilee, spread out his arms, and say, “You see the shape of this hillside? It’s a natural amphitheater! Jesus could have stood right here and preached to thousands of people without a microphone!”
Maybe.
But that’s not really the point. We don’t even know whether Jesus went up the mountain so the crowd could hear Him better, or because He wanted to get away from the crowd. And I’m always a little suspicious when a tour guide can point to the exact rock Jesus stood on two thousand years ago—because there is almost always a gift shop nearby!
The crowds are there. Matthew doesn’t let us forget them. In fact, when the sermon ends in chapter 7, Matthew tells us that the crowds were astonished at His teaching. So obviously they could hear what Jesus was saying.
But Matthew specifically says that Jesus’ disciples came to Him, He sat down, and He taught them.
Sitting down, not standing up.
Teaching the disciples, not preaching to the crowd.
I point that out because I think sometimes people, especially in the Bible Belt, have been preached to death. We’ve seen plenty of preachers and evangelists who can draw big crowds with their PROCLAMATION! And they are well practiced with their GESTICULATION! And they can convince us of their sincerity by the amount of AGITATION!
But I believe what the church desperately needs is solid, biblical, TEACHING.
We don’t want to lose sight of the evangelistic mandate. Jesus told us to make disciples of all nations. But the Great Commission doesn’t end with making converts. Jesus said, “teaching them to observe all that I have commanded you.”
And that’s what Jesus models here. This is kingdom teaching for disciples.
We don’t have the Sermon on the Mount because somebody standing in the back row of a crowd of thousands happened to be taking really good notes.
We have it because Jesus taught His disciples, and His disciples preserved His teaching.
Now, I love The Chosen. I think that show has captured the humanity and personalities of the people who followed Jesus probably better than anything I’ve ever seen.
But I do think the episodes leading up to the Sermon on the Mount may take the creative license a little too far. If you remember, Jesus is working on the sermon and going over His outline with Matthew.
That’s a great scene. It’s just not in the Bible.
The calling of Matthew to be a disciple isn’t even recorded until chapter 9. Now, that doesn’t necessarily mean Matthew wasn’t there—Matthew isn’t always arranging everything in strict chronological order. But it does mean we shouldn’t picture Jesus wordsmithing His sermon with Matthew. Jesus wasn’t like, “Matthew, in this section, should I say consider the birds, or consider the squirrels?”
Matthew 5:2 simply says, “And he opened his mouth and taught them.”
Not, “He opened His sermon notes and taught them.”
Jesus sat down.
His disciples came to Him.
And Jesus taught them.
And that distinction matters, because Jesus isn’t primarily telling the world how to behave. He’s telling His followers what life in His kingdom looks like.
The crowds want to know what to make of Jesus.
The disciples need to know what Jesus is going to make of them.
And then Jesus begins.
Not with a battle plan. Not with a strategy for overthrowing Rome. Not with a list of the people who are finally going to get what’s coming to them.
He begins with one word:
“Blessed.”
And the first people He calls blessed are the last people anyone in that crowd would have expected:
“Blessed are the poor in spirit, for theirs is the kingdom of heaven.”
THE TEACHING
Jesus begins with one word:
Blessed.
The Greek word is makarios. And sometimes you’ll hear people say that makarios means “happy.”
That’s not exactly wrong. But I don’t think happy communicates everything Jesus is saying here, because when we hear the word happy, we usually think about how we feel.
And Jesus isn’t describing a feeling. He’s making a pronouncement. He’s declaring that this is a person who is truly well-off in the eyes of God.
Think about some of the people Jesus is going to call blessed.
“Blessed are those who mourn.”
Do grieving people necessarily feel blessed?
“Blessed are those who are persecuted for righteousness’ sake.”
Do people who are insulted and lied about and mistreated because they follow Jesus necessarily feel blessed?
Of course not.
So Jesus isn’t saying, “These people feel really good about their lives.”
He’s looking at people the world might call unfortunate, unsuccessful, or even cursed, and He’s saying:
“No. I say this person is blessed.”
This matters to us because there are times in your life when you are blessed even though you don’t feel blessed.
There are times when your circumstances seem to contradict the pronouncement Jesus has made over your life.
But the blessing doesn’t depend on how you feel about your circumstances.
It depends on what the King says is true about you.
And the very first people the King calls blessed are:
“the poor in spirit.”
Now, in Luke’s version of the Beatitudes, Jesus says,
“Blessed are you who are poor, for yours is the kingdom of God.”
So which is it— the poor, or just the poor in spirit?
Yes.
Throughout Luke’s Gospel, Jesus has a particular concern for people who are actually poor—for people without money, power, or social standing.
But Matthew says,
“Blessed are the poor in spirit.”
That doesn’t mean poverty itself makes someone righteous. And it doesn’t mean having money makes someone unrighteous.
You see, Luke won’t let comfortable Christians forget the materially poor, and Matthew won’t let rich Christians ignore their own spiritual poverty.
In fact, one of the best pictures in the Bible of what it means to be poor in spirit may have been a man who wasn’t financially poor at all. Please turn to Luke 18:9-14
AN EXAMPLE FROM SCRIPTURE
Jesus told a story about two men who went to the temple to pray.
One was a Pharisee.
And his prayer was basically a résumé.
“God, thank You that I’m not like other people. I’m not an extortioner. I’m not unjust. I’m not an adulterer. I’m certainly not like that tax collector over there. I fast twice a week. I tithe everything I get.”
He’s standing before God with his pockets full.
Look what I’ve done. Look what I’ve accomplished. Look what I can offer You.
But the tax collector stands at a distance. He won’t even lift his eyes toward heaven. He beats his chest and says:
“God, be merciful to me, a sinner!”
And here’s the irony:
The tax collector may have had plenty of money.
But he knew he was broke.
Spiritually, he had nothing in his pockets.
Nothing to bargain with.
Nothing to brag about.
Nothing to impress God with.
All he could do was ask for mercy.
And Jesus said that man went home justified.
That’s poverty of spirit.
In fact, here’s the distinction I want us to understand:
Everybody is spiritually poor. The poor in spirit are the ones who know it.
Every one of us comes before God spiritually bankrupt. The question is whether we recognize it.
Because you can be financially poor and spiritually proud.
And you can be financially wealthy and poor in spirit.
Poverty of spirit means I have stopped trying to convince God that He ought to be impressed with me.
My morality doesn’t impress Him.
My church attendance doesn’t impress Him.
The fact that I’m a Baptist doesn’t impress Him.
My Bible knowledge doesn’t impress Him.
My giving doesn’t impress Him.
My ministry doesn’t impress Him.
I come to God with empty hands.
And Jesus says:
“Blessed are the poor in spirit.”
But don’t miss the second half:
“For theirs is the kingdom of heaven.”
There’s something different about that promise.
Look at the Beatitudes that follow.
Those who mourn will be comforted.
The meek will inherit the earth.
Those who hunger and thirst for righteousness will be satisfied.
The merciful will receive mercy.
The pure in heart will see God.
There is a future dimension to those promises.
But Jesus doesn’t say,
“Blessed are the poor in spirit, for theirs will be the kingdom of heaven.”
He says:
“Theirs IS the kingdom of heaven.”
And when we get to the eighth Beatitude, we’re going to hear exactly the same thing:
“Blessed are those who are persecuted for righteousness’ sake, for theirs is the kingdom of heaven.”
That’s not an accident.
Those two statements form brackets around the Beatitudes.
We begin with the kingdom.
We end with the kingdom.
Which means these aren’t eight steps you climb until you’ve finally done enough for God to let you into His kingdom.
The kingdom isn’t the prize waiting at the top of the Beatitude ladder.
The kingdom is where the Beatitudes begin.
And how do you enter a kingdom you can’t earn your way into?
With empty hands.
That’s why Jesus begins here.
Before mourning.
Before meekness.
Before hungering for righteousness.
Before mercy.
Before purity.
Before peacemaking.
Before persecution.
First, I have to recognize that I bring nothing to the table.
Blessing begins with brokenness.
And maybe that’s why the kingdom belongs to the poor in spirit.
Because as long as my hands are full of everything I think I have to offer God, I can’t receive what He is offering me.
But when I finally open my empty hands—
“Theirs is the kingdom of heaven.”
INVITATION
You may have known someone who went through a twelve step program. Or you may be going through one yourself. One thing they all have in common, whether they are for alcoholics, or substance abusers, or people addicted to pornography or gambling, is that they all begin with: ““We admitted we were powerless over ____________—that our lives had become unmanageable.”
Notice how much that has in common with “Blessed are the poor in spirit.”
The first step isn’t, “I’m going to do better.”
It isn’t, “I’m going to try harder.”
It isn’t, “I’m going to get my act together.”
The first step is an admission:
“I am powerless.”
Now, the Beatitudes aren’t a Twelve Step program, and Christianity isn’t self-help. In fact, it’s exactly the opposite of SELF help.
Before anything can change, I have to admit that self help is no help at all.
You might have seven figures in your bank account.
Or you might not have seven dollars in your wallet.
You might have a wall covered with diplomas and awards.
Or you might wonder how you’re going to make it through this week.
You may have been in church your entire life.
Or this may be the first time you’ve walked through the doors of a church in years.
The ground is level at the foot of the cross.
Every one of us comes to Jesus the same way:
Empty-handed.
Nothing to bargain with.
Nothing to boast about.
Nothing that puts God in our debt.
Just the prayer of the tax collector:
“God, be merciful to me, a sinner.”
And here’s the good news.
Jesus doesn’t say, “Get yourself together, and then maybe the kingdom can be yours.”
He says:
“Blessed are the poor in spirit, for theirs IS the kingdom of heaven.”
Not because brokenness earns you anything.
But because brokenness finally stops pretending that you can earn it.
That’s why we put those two little words on the bottom of that license plate:
Sola gratia.
By grace alone.
You don’t buy your way into the kingdom.
You don’t behave your way into the kingdom.
You don’t impress your way into the kingdom.
You receive the kingdom with empty hands.
So maybe the first step for you this morning is simply to admit:
“I need Jesus.”
And if you’ve never trusted Him, that’s where the blessed life begins.
But maybe you’ve followed Jesus for fifty years. Don’t make the mistake of thinking you graduate from poverty of spirit.
We never outgrow our need for grace.
The longer I follow Jesus, the more clearly I ought to see how desperately I need Him.
So whether today is the first time you’ve ever come to Jesus, or the ten-thousandth time you’ve come back to Him, we come the same way:
Empty hands.
Open heart.
Nothing to prove.
Everything to receive.
Blessing begins with brokenness.
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