Good morning, church. My name is Andy Henderson. I’m one of the pastors here at North Hills.
It’s not an easy task to teach about the dangers of hypocrisy. God had a way of reminding me over and over again as I studied that I struggle pretty deeply with this. Ryan mentioned last Sunday that he’s a recovering hypocrite, and I’m certainly right there beside him. Just one story of unfortunately many, this happened last week:
I’m driving. My wife will tell you that I don’t have a lot of patience with people who are at red lights and the light turns green and they don’t move. So I just popped my horn (I honestly did), but inside, I was really frustrated.
So I get to the church, go out a couple hours later, and I’m the person at the front of the line at a red light. I’m daydreaming, the person behind me pops their horn, and my first response is, “Hey, just be patient.” I was daydreaming about this sermon, so God has a way of pointing things out. I would really love to preach one day on the dangers of overwhelming prosperity to see if maybe God will use that same method.
How often I judge people by their actions and assign to them the worst possible motivations and intentions. But when I do the same actions or similar actions, I assign myself much purer motivations and intentions. When you fail, I see what you did. When I fail, I know why I did it. The reason always sounds better from the inside.
Your actions are visible and concrete. My intentions are private and flexible. And I always find a reason to excuse myself: “I was stressed,” “I was provoked,” “I was tired,” “I was protecting something good.” The road to my failure is paved with good reasons. The road to yours is just failure. And I doubt that I’m alone in that.
That dynamic is what allowed the Pharisee in Luke 18 to stand in the temple and look down on the tax collectors. He was begging God for mercy and genuinely believed that he was the righteous one in that story. He wasn’t performing for the crowd in that moment. He was alone with God, and he still couldn’t see it. That’s how deep hypocrisy goes.
Over the last few weeks, we’ve been looking at this Greek word, “hupokrites,” from which we get our English word, “hypocrite.” It’s a Greek word that Jesus actually used many times in Matthew’s Gospel. In fact, I do not believe that any other term of moral description appears with that frequency. He talked about hypocrisy a lot.
We tend to use the word “hypocrite” as an accusation. But before it was an accusation, it was actually a diagnosis.
The word “hypocrite” comes from Greek theater, or at least it was used in that a lot. It simply meant an actor or a pretender, someone who played a role from behind a mask. That’s what the word meant. In that context, the mask was an art form. Everyone knew it was a performance. Nobody’s looking at the person on the theater stage and saying, “Oh, they’re being deceptive.”
What Jesus does with the word is to move it from the realm of the theater into the realm of the temple. The Pharisees have turned their religious life into a performance, and that’s what the last three weeks have been in Matthew 23. They’re wearing masks, and unlike the theater, nobody’s supposed to know.
Before hypocrisy is a sin, it’s a fracture. Peter mentioned three weeks ago that hypocrisy is the opposite of wholeness. That statement has stuck with me ever since. In one sense, of course, as believers (those of us who are in Christ), we are complete from a positional sense. There’s nothing more that we need. But from a practical sense, we are very fractured at times.
The biblical vision of human health is wholeness. “Shalom,” in Hebrew. We use that term. We say it means peace, and in one sense it does, but it’s a peace that goes beyond what we typically think of as peace, maybe, into completeness. Nothing missing. Nothing is broken. That’s what shalom means.
The English word “integrity” comes from the Latin word “integer,” which means whole, all of one piece. A person who has integrity is someone whose public self and private self are the same. There’s no gap.
Hypocrisy is the opposite. It is actually disintegration, the fracturing of the self into the person you pretend to be and the person you actually are. That fracture has consequences. Once the gap opens, it has to be maintained. Enormous energy can go into managing appearances. The integrated person, the person with integrity, has nothing to manage. The hypocrite is always managing.
In his book, The Scarlet Letter, Nathaniel Hawthorne wrote these words:
“No man, for any considerable period, can wear one face to himself and another to the multitude, without finally getting bewildered as to which may be the true.”
But the consequences of hypocrisy go well beyond just simply appearance management. We see this in the life of the Pharisees and the other religious leaders of Christ’s Day. We see that in our culture today. This hypocrisy had a drastic impact on their lives and the religion that they were trying to cultivate.
As the Pharisees proved, where there is rampant hypocrisy, there will be a lack of transparency. You can’t be truly known when you’re always performing. In fact, we don’t really want to be truly known. There’s a lack of teachability when your identity depends on already being right. New truth is a threat.
Where there is hypocrisy,
And hypocrisy is not just one thing. There are levels of it in the human heart. We actually find all of these levels right here in the book of Matthew, from the most common level of hypocrisy to the most destructive.
Level 1 – The Universal Hypocrite
The most common would be level one. It’s universal hypocrisy. In its most basic sense, level one includes every human being. We were made in the image of God (the Imago Dei), and not one of us lives up to that all the time. The gap between what we were made to reflect and what we actually are is the most universal fracture there is.
For those of us who are believers, there’s a second layer to this: We are in Christ. We bear his name. We are indwelt by his Spirit, and we still don’t always live like it. There’s a fracture that’s there.
This level also includes those who do not live up to their own standards. The gap between who we say we are and who we actually are. This is the disciples (Peter especially) in Matthew 26, claiming vehemently that even if they were called upon to die, the one thing they would never do is deny Jesus. A few hours later, we find the disciples scattered because of fear and Peter denying that he even knew Jesus, not once, but three times.
If we’re honest, level one is where we are on most, if not all, days. We don’t live up to our own standards. We don’t live up to the image that we bear. We don’t live up to the identity that we have in Christ.
Level 2 – The Self-Deceived Hypocrite
Level two, self-deceived hypocrisy. This goes a step further, not just falling short of our own values, but constructing a self-image that hides the failure even from ourselves. We’ve convinced ourselves that the gap doesn’t exist, even though others clearly see it. Hypocrisy is truly one of those things that we clearly see in others, but we don’t so clearly see it in us.
Think of the rich young ruler back in Matthew 19 that we studied. He sincerely believed he had kept all the commandments from his youth. He really believed that. Jesus didn’t argue. He asked one question that put his finger precisely on the one thing the man had hidden from himself. The man walked away grieving because the self-deception had been exposed, and he wasn’t ready to let it go.
Level 3 – The Performative Hypocrite
Level three is performative hypocrisy. This describes those who attempt to curate a false image. When we hear the word hypocrisy, this might be the level that we think about most: The conscious management of reputation, the creation of a spiritual image for public consumption.
We see this back in Matthew 6, back in the Sermon on the Mount. As the Pharisees and other religious leaders were giving, and as they were praying and as they were fasting, it was all done to be seen.
They would make themselves look haggard and sad when they were fasting so that everybody looking at them would know, “Oh, they’re fasting.” Some of them would actually have people blow trumpets when they were walking up to give, so that all the attention would be on them as they gave. Or they would stand on street corners and pray out loud so that everybody could see them and hear them praying, all to be seen by others and praised. As Jesus mentions just earlier in Matthew 23, they were whited sepulchers filled with dead men’s bones.
Another group that fits into this category, I believe, is those who speak loudly against something that they themselves are doing in secret. One persona in public, another persona in private.
Level 4 – The Weaponized Hypocrite
Level four—and I think this is where it really begins to get really destructive—is weaponized or exploitative hypocrisy. This is one who uses righteousness as a tool of power. It’s beyond performative, into the predatory piety displayed as a tool of power and control.
Just a few verses before this, in Matthew 23, we find the Pharisees devouring widows’ houses while making long prayers. They were showing this righteousness so that they could actually exploit. The religious exterior was a cover for exploitation. That’s weaponized hypocrisy.
Level 5 – The Diabolical Hypocrite
Level five is diabolical hypocrisy. This is the final form. It’s more than exploiting. It’s what Paul describes in 2 Corinthians 11:14, Satan masquerading as an angel of light. Satan’s not masquerading as an angel of light so that his reputation would be good, or just so that he could exploit somebody. He does it so that he can destroy. Back in Matthew 4, we see Satan as he is quoting scripture to Jesus, tempting him to sin so that he might destroy him.
What we’re going to find in the passion narrative here in Matthew, coming up later on, is the religious leaders using the legal and religious machinery to eliminate Jesus while maintaining the appearance of due process. They wanted to look like they were doing right in order to destroy.
Then there’s Judas in the Garden of Gethsemane (the kiss on the cheek), where the gesture of intimacy becomes the instrument of death. He wanted to destroy Jesus.
Five levels. If we’re all honest, we all fit somewhere on that spectrum. Even though we all struggle with it, hypocrisy is one of the main reasons why people have left church in Christianity. Hypocrisy is hurtful. It has done great damage.
What we want to discover this morning is Jesus’s heart for the hypocrite. How does he approach our hypocrisy? It’s a big deal to Jesus. He certainly doesn’t minimize it. He doesn’t downplay it. His response in our text for this morning revealed how he considered hypocrisy.
1. Hypocrisy warrants grief.
The first one is this. Hypocrisy warrants grief. It’s deserving of grief.
“O Jerusalem, Jerusalem, the city that kills the prophets and stones those who are sent to it! How often would I have gathered your children together as a hen gathers her brood under her wings, and you were not willing!” (Matthew 23:37)
Jesus uses a literary device here, double address, that communicates deep emotion, concern, and even intimacy at times. We’ve seen it before in the book of Matthew. Frankly, I think this is one of the most horrifying passages to me in all the Scriptures, Matthew 7:22-23.
“On that day many will say to me, ‘Lord, Lord, did we not prophesy in your name, and cast out demons in your name, and do many mighty works in your name?’ And then will I declare to them, ‘I never knew you; depart from me, you workers of lawlessness’” (Matthew 7:22-23).
Can you pick up the desperation in their voice as they realize what is about ready to happen, and so they use this double address, “Lord, Lord.” Jesus himself uses this literary device on several occasions.
“But the Lord answered her, ‘Martha, Martha, you are anxious and troubled about many things” (Luke 10:41).
“Simon, Simon, behold, Satan demanded to have you, that he might sift you like wheat” (Luke 22:31).
“Saul, Saul, why are you persecuting me?” (Acts 9:4b)
We’re going to see as Jesus is being crucified in Matthew 27,
“My God, my God, why have you forsaken me?”
Here in Matthew 23:37,
“Jerusalem, Jerusalem.”
Ryan mentioned last week that grief has really been running through Jesus’s words to the Pharisees, and we see the same thing here. There’s a deep lament in these words.
Jesus here moves from speaking directly to the religious leaders, and now he branches out to look at the nation as a whole— represented by Jerusalem, its capital. These are the final words that Jesus speaks to the nation of Israel publicly. This is it.
The hypocrisy of the nation had been a constant theme in both the Old and the New Testaments. There are several passages we could go to, but I just want to look at Isaiah 58:1-5. As God tells Isaiah to…
“Cry aloud; do not hold back; lift up your voice like a trumpet; declare to my people their transgression, to the house of Jacob their sins.
I want you to point these things out to them. It’s curious the very next words.
“Yet they seek me daily and delight to know my ways, as if they were a nation that did righteousness and did not forsake the judgment of their God; they ask of me righteous judgments; they delight to draw near to God. [And they say to God,] ‘Why have we fasted, and you see it not? Why have we humbled ourselves, and you take no knowledge of it?’ Behold, in the day of your fast you seek your own pleasure, and oppress all your workers. Behold, you fast only to quarrel and to fight and to hit with a wicked fist. Fasting like yours this day will not make your voice to be heard on high. Is such the fast that I choose, a day for a person to humble himself? Is it to bow down his head like a reed, and to spread sackcloth and ashes under him? Will you call this a fast, and a day acceptable to the Lord?” (Isaiah 58:1-5)
We find these sentiments over and over again about the nation. They were passionate about the form of worship while ignoring the true object of worship. Like the Pharisees, their hypocrisy ran deep and was destructive. Jesus says, “…the city that kills the prophets and stones those who are sent to it!”
That present tense in the Greek is significant. Killing prophets is not something that Jerusalem once did, like they did it one time, or they did at some time in the past. It’s something that Jerusalem does. It’s a pattern. It is, in many senses, their legacy.
The history behind that pattern is long and painful. Think of Jeremiah, God’s weeping prophet, called to preach repentance to a nation that had exchanged the living God for idols while maintaining the full religious apparatus: the temple, the sacrifices, the feasts, all of it running perfectly while the heart was entirely elsewhere. In Jeremiah 7, God says,
“Will you steal, murder, commit adultery, swear falsely, make offerings to Baal— and then come and stand before me in this house and say, ‘We are delivered!’?” (Jeremiah 7:9a, 10a)
That’s Level 3 and level four hypocrisy on a national scale. Religion as an alibi, the temple as a cover for wickedness. What did they do to Jeremiah? They did a lot to Jeremiah if you read the book, but one of the things was they threw him in a cistern for days on end. They wanted him dead.
Think of Isaiah, whom we just read of in Isaiah 58. Tradition holds that he was sawn in two under the reign of Manasseh. His crime was telling the truth to a people who had perfected the art of looking righteous while running after everything but God. Here are words from Isaiah 29, and they sound very familiar to us.
“…this people draw near with their mouth and honor me with their lips, while their hearts are far from me” (Isaiah 29:13b).
Jesus quoted this passage in Isaiah back in Matthew 15 about the Pharisees. The pattern runs deep, and the words are eerily similar across the centuries.
Think of Zechariah. Ryan mentioned him last week in his text. Jesus mentioned sins explicitly in Matthew 23:35. You can read the story in 2 Chronicles 24: the priest who stood in the temple and told the truth, stoned by order of the king.
God kept sending messengers over and over again. These were people God personally dispatched to deliver truth to the nation for their own flourishing, and they were killed one after another. Generation after generation, and now the Son himself has come, and he knows exactly what is going to be happening to him in the next couple of days.
But even with all of that hurt and betrayal, Christ still approaches the nation with tenderness and grace. Repeatedly, he says,
“How often would I have brought you near if you had just repented? I would have gathered you and your children like a hen brings her chicks under the shelter of his wings.”
The image would not have been lost to the nation because the Old Testament used this imagery often to speak of warmth and protection and refuge. But they refused that grace. Jesus says,
“You were not willing.”
It’s amazing how unlike Jesus I can be. When I encounter hypocrisy, I tend to denounce it in others and dismiss it within myself. What I almost never do is grieve for the person trapped in it. That’s usually not my emotion.
Jesus, who had just preached what is probably the most devastating sermon on the subject of hypocrisy, grieves. Full confrontation with genuine heart lament, both fully present. I think this is the posture this passage calls us to, and this is not downplaying the devastating effects of hypocrisy or the nature of it.
2. Hypocrisy warrants judgment.
Hypocrisy warrants grief. It deserves grief for those in bondage to it, but it also warrants judgment. That’s the second thing we see in verse 38: “See, your house is left to you desolate.” Jesus seems to be looking at the temple, and he calls it “your house.” Not my house, not God’s house. Your house.
The temple was designed to be a place of divine presence and divine name, and now Jesus withdraws that designation. It has become simply “your house,” a religious institution emptied of the presence that gave it meaning through hypocrisy.
The word for “desolate” here that we find is a word that carries with it the idea of uninhabited wilderness. It’s a place of absence and barrenness. What was meant to be a house of prayer becomes a wasteland, Jesus says. The historical fulfillment of this, the physical fulfillment of these, will happen a few decades from then, when Titus in AD 70 destroyed Jerusalem stone by stone, exactly what we will find in Matthew 24.
But the spiritual desolation precedes the physical one. The presence has already departed. The religious machinery keeps running. It keeps going (sacrifices and prayers and feasts), but the glory of God has departed. That’s the most sobering form of judgment. Not dramatic destruction, but quiet withdrawal.
Persistent, unrepentant hypocrisy does a lot of damage to others, but it also empties us. We can maintain the forms of religion meticulously on the outside, and all the while be spiritually cold on the inside. The whitewashed tomb that Jesus had just mentioned not all that long before this is not a ruin. It’s beautiful. It’s polished and maintained. You would not know what was inside unless you had been inside.
3. Hypocrisy warrants hope.
Hypocrisy warrants judgment, not because God is harsh, but because God is holy. Willful refusal has consequences, but the beautiful thing is this verdict is not the last word, because hypocrisy warrants hope. Verse 39:
“For I tell you, you will not see me again, until you say, ‘Blessed is he who comes in the name of the Lord” (Matthew 23:39).
His final, public words to the nation of Israel are ones of hope. Did you catch that word “until?” He doesn’t say “you’ll never see me again,” and leave it there. It’s not a door slammed and locked. “You will not see me— until.” There’s a hinge in that sentence, and hanging on that hinge is hope.
As we mentioned a few chapters ago, Jesus is quoting Psalm 118:26a,
“Blessed is he who comes in the name of the Lord.”
Now, the crowds have already shouted this back in Matthew 21 at the triumphal entry. So why does he say, “You will not see me until” you say these words when they’ve already been said? Because this is separate. We are looking here at something in the future. This is looking toward the coming of Christ in all of his glory.
Next week, we’re going to begin a several-week study of the Olivet Discourse in Matthew 24 and 25. The Olivet Discourse is a call for Christ followers to be watchful and faithful, for the return of Christ is certain. Peter promised that he’s going to have charts and graphs and exact dates for you, so you want to come and hear that. Please don’t tell anybody that we said that. I’ll be fired.
The judgment is real, the desolation is real, but the “until” means that the story is not over. The grieving, judging, hoping heart is not unique to our text. It runs throughout the gospels. Watch what Jesus does with people from every level of hypocrisy that we started with.
Level one, universal hypocrisy: the disciples who fell asleep in the garden. Then they fled when they should have been standing up for Jesus, and they failed. They said they were not going to do that, and they did it. Then after the resurrection, Jesus says, “I’m not done with y’all. Go and make disciples of all nations.” There was restoration.
Level two, self-deceived hypocrisy: the rich young ruler who walked away, that we talked about. If you look at Mark’s account of that story, there’s a beautiful little phrase in there. Before Jesus asked him that hard question, Mark mentions that Jesus looked at him and loved him. The door was not closed.
Levels three and four, the performative and weaponized hypocrisy: Joseph of Arimathea, a member of the council that condemned Jesus, came forward to claim the body. Matthew records that — without condemnation — the man (most likely Joseph) had been complicit in silence, and he’s the one who provides the tomb.
Nicodemus, a Pharisee who came to see Jesus in the middle of the night so he wouldn’t be seen by others, was welcomed into a conversation about the gospel by Jesus and became a follower.
Level five, the diabolical hypocrite: Judas in the garden, the kiss of betrayal. Anybody remember what Jesus called him at that moment? Friend. This was genuine. It wasn’t sarcasm. The door was still open. Judas closed it himself.
One more scene, maybe my favorite. One of my favorite scenes in all of the Gospels: John 21. Peter, who swore he would die before denying Jesus. Within hours of that, he had denied him three times with escalating intensity, the third time with curses and oaths.
After the resurrection, Jesus is waiting for him on a beach with a charcoal fire going. That detail is important. It’s deliberate. John 18:18 records that Peter made his denials while warming himself at a charcoal fire. John 21:9 uses the exact same word. Jesus brought Peter back to the scene of the worst night of his life and made him breakfast.
“Simon, son of John, do you love me?”
Three times he asks, one for each denial. There’s restoration. The same heart that grieved over Jerusalem earlier in the week (in our text today) was on that beach shortly after his resurrection for a man who had sworn three times he didn’t even know him. That’s the heart of Jesus for hypocrites. Grief, judgment where it’s warranted, and — for those who turn and repent — there’s hope, and there’s restoration.
But I want to push the “until” further than Jerusalem, because what Christ’s return means for those of us who are in him is not just a moment of recognition — a moment where there will be no more pain and suffering — it’s the end of the fracture itself.
Remember how we started this morning: Hypocrisy is a disintegration, the splitting of the self into the person you perform or pretend to be and the person you actually are. The gap between the face that you show and the reality you hide, the mask that eventually becomes so familiar some of us even forget we’re wearing it.
The return of Christ means the permanent end to all of that. For those who are in him, glory is not just forgiveness, it’s wholeness. We’re going to wake up whole. Complete, final, irreversible wholeness. Think about what that actually means:
It means being fully known and being fully loved at the same time.
Fully known by others and fully loved, perhaps for the first time in our relational experience. We know that God loves us. He knows us well, and he still loves us. Romans 8 settles that: Nothing will separate us from the love of God in Christ. But our human relationships have never fully felt safe for transparency.
Full disclosure often carries a lot of risk. People may leave. People may use what they know against us. It’s still so important to be transparent for healing, but in glory, that risk is gone. It’s going to be a community of people fully known to one another and fully at peace with one another. No more posturing, no more management, no more protective distance. That is something we’ve never experienced fully and will not fully experience until then. No need to be better than the person next to you. Both are complete in Christ, both whole. The mask is not just removed, it no longer exists.
Secondly, it means the image of God is fully restored.
We grounded level one hypocrisy this morning in the image of God, the gap between what we were made to reflect and what we actually are. We see God’s purposes for all of his people in Romans chapter 8:29b, that we would be “conformed to the image of his Son.”
“…we shall be like him, for we shall see him as he is” (1 John 3:2b).
The fracture that entered the world in Genesis 3 — the hiding, the covering, the blame-shifting — the first real performance permanently reversed. We’re going to bear that image without distortion and without gap. For those of us who are in Christ, we will finally live up to that identity in every way.
Thirdly, it means authentic worship, finally and completely.
One of the things that hypocrisy really prevents is genuine worship. There are times when we have lips that are honoring God while our hearts are far from him. In glory, that gap is gone. It will no longer exist.
The worship that you find in places like Revelation 4 and 5 is worship with no performance motive, and there’s no reputation management going on. There’s no distance between what is said and what is being felt. For the first time in our existence, we will worship with complete integrity — the whole self, fully present, fully meaning every word. That is the “until” of Matthew 23:39, the beginning of an existence in which hypocrisy will be permanently, structurally impossible because everything that produced it is gone.
Here’s the hope that this passage will not let us escape: Heaven’s going to be filled with redeemed hypocrites. Filled.
We have an opportunity to celebrate that hope this morning in a very tangible way together. In a few moments, we’re going to be observing communion. I want you to understand what the table is: This is not a table you see right here for the whole, it’s a table for the fractured.
Jesus knows where you’ve been. He knows the gap between your profession and your practice, and he invites his broken people to this table. The bread is his body broken for hypocrites. The cup is his blood shed for hypocrites. What we just said about glory — the fracture being healed, the image restored, the mask dissolved — this table is in anticipation of all of that, what we are doing this morning.
One day the gathering will be complete. One day we will all gather together at the marriage supper of the Lamb, a community of the fully known, the fully loved, the full whole. No performance, no gap, no mask. Just the redeemed, finally and completely themselves in the presence of the one who knew them intimately all along and loved them anyway. This table points to that one. Communion is for those who have placed their faith and trust in Jesus for their salvation.
If you’re still considering that, if you still have questions, or if you know “that’s not me,” we would ask that you let the bread and the cup pass by and spend this time in self-examination and in prayer. Of course, if you have any questions about what it means to be “in Christ,” would you please grab somebody here? We would love to show you what that looks like and what it means. It’s glorious.
In just a moment, we’re going to be singing. As we do, those who will be passing out the elements can come. After we sing a couple of songs, we’ll take communion together. The first song we’re going to sing, “In Christ Alone,” is a glorious anthem of the hope that we have in Christ. I’m looking forward to singing that together with you. Let’s pray.
Father, unite our hearts, undivide our hearts so that we may worship you fully this morning. God, that was a prayer from the psalmist. We thank you, Father, that in your Son, Jesus, we are—in one sense—complete. God, I pray that you will clearly reveal to us where we are still hypocritical in our own lives, not for shame and not to feel guilt, but to experience your perfect forgiveness and love and grace. It’s in the name of your Son, Jesus, that we pray these things, amen.
