Woe to You, Hypocrites

Introduction

If you’ve ever watched a UFC title fight, you know the feeling before the main event. The lights dim. The arena is electric. Two fighters who have been circling each other for months—sometimes years—are finally about to step into the octagon. There’s tension, anticipation, and a sense that something decisive is about to happen.

This isn’t a friendly sparring match. This is the main card. Heavyweight stakes. Every move matters.

By the time we get to Matthew 23, Jesus has entered Jerusalem, and the tension has been building. The Pharisees have questioned Him, challenged Him, tried to trap Him publicly. There’s been a back-and-forth all throughout His ministry—but now, we’ve reached the final round.

And Jesus doesn’t come out soft.

He steps into the “octagon” of the temple courts and delivers a series of devastating blows—not with fists, but with truth. “Woe to you, scribes and Pharisees, hypocrites…” Over and over again. This is not uncontrolled anger. This is precise, righteous judgment. Every word lands with authority. Every statement exposes what’s been hidden.

It’s the kind of moment where you realize: this isn’t just another teacher. This is the King confronting false religion head-on.

And what’s at stake isn’t a belt or a title—it’s the souls of people who have been misled by leaders who look holy on the outside but are empty within.

Matthew 23 is Jesus’ final rebuke, His last public takedown before the cross. And if we’re honest, it doesn’t just expose the Pharisees—it forces us to ask whether any of that same hypocrisy is still fighting for space in our own hearts.

So, how does Jesus throw his punches? Primarily, with this heavy right hook: over and over again.

Hypocrite. We will see Jesus use this word six times to describe the scribes and Pharisees in our text tonight.

In Greek, this word is hupokrites, which comes from the word hupokrinomai, meaning “play the part.”

Our culture is all about playing the part. Just looking a certain way. Who cares what is really going on in your life? Social media has crippled authenticity in our generation. We live in a world that not only thrives on hypocrisy, but actively promotes it.

Jesus proclaims seven (some translations have an eighth - ask me afterwards if you want to know why I am only preaching on seven.. Be curious about God’s word!) woes (or condemnations) upon the religious authorities.

This is one final opportunity for the Pharisees to understand their spiritual deadness, and come to Jesus for life. Their response to Jesus’ fierce rebuke in this passage will determine whether they enter into God’s kingdom, or are cast into the fire.

This interaction is with the religious elites under an entirely different culture and religious system than we have today. What are we supposed to take from this? It has been said that the Bible was written for us, not to us. So why would Matthew record this severe story, and why would it make its way to us, here and now?

I believe the central point of this story is this:

Main Idea: Jesus recognizes and condemns hypocritical faith. Those who follow him, genuinely and humbly, will be saved from condemnation.

I am going to begin reading in Matthew 22:41 and work through our passage and explain things as we go.

Matthew 22:41–46 ESV

41 Now while the Pharisees were gathered together, Jesus asked them a question, 42 saying, “What do you think about the Christ? Whose son is he?” They said to him, “The son of David.” 43 He said to them, “How is it then that David, in the Spirit, calls him Lord, saying, 44 “ ‘The Lord said to my Lord, “Sit at my right hand, until I put your enemies under your feet” ’? 45 If then David calls him Lord, how is he his son?” 46 And no one was able to answer him a word, nor from that day did anyone dare to ask him any more questions.

Remember, this is right after Jesus had deftly avoided another trap set by the scribes regarding the Greatest Commandment. So, Jesus turns things back upon them with this seeming paradoxical reality present in the Old Testament Messianic prophecies. If the Messiah, the Christ, is the son of David, then he must surely be inferior to David. Yet, David refers to his own Messianic son as Lord, clearly demonstrating that David recognizes him to be superior to himself.

How can the Messiah be inferior and superior to David? It was because the Messiah was not just a man, nor was he just God. But he was to be the God-Man. The Pharisees knew that Jesus was referred to as the son of David. Many called him Christ and Messiah. They know the implicit undertone of his question: What do you think about the Christ? About me? Whose son am I?

They could not understand, despite all the evidence and signs before them, that Jesus was God manifest in the flesh, the very son of David whom David would call Lord.

This confusion shuts down any further attempts from the Pharisees to win a public debate against Jesus and discredit him. They’ve been duking it out round after round, and now, with his opponents sluggish and worn out, the fight on the main card enters its final stage. He is about to go full Jesus JiuJitsu here. Let’s tap into chapter 23.

Here's the flow: 1. Jesus calls followers to humble faith (vv.1–12). 2. He condemns hypocritical leaders (vv.13–36). 3. He laments unbelief. (vv.37–39).

Matthew 23:1–12 ESV

1 Then Jesus said to the crowds and to his disciples, 2 “The scribes and the Pharisees sit on Moses’ seat, 3 so do and observe whatever they tell you, but not the works they do. For they preach, but do not practice. 4 They tie up heavy burdens, hard to bear, and lay them on people’s shoulders, but they themselves are not willing to move them with their finger. 5 They do all their deeds to be seen by others. For they make their phylacteries broad and their fringes long, 6 and they love the place of honor at feasts and the best seats in the synagogues 7 and greetings in the marketplaces and being called rabbi by others. 8 But you are not to be called rabbi, for you have one teacher, and you are all brothers. 9 And call no man your father on earth, for you have one Father, who is in heaven. 10 Neither be called instructors, for you have one instructor, the Christ. 11 The greatest among you shall be your servant. 12 Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.

Jesus calls his followers to have humble, obedient faith. -v.1-12

Jesus first addresses the crowds that were gathered around. When Jesus says that the scribes and Pharisees sit on Moses’ seat, he is saying that they speak from the Law from the position of authority of Moses. He encourages the people to do what the Pharisees teach them, but do not do the things they see the Pharisees doing.

Jesus does not mean that the people are to literally do everything the Pharisees do, as we will see later in the chapter. What Jesus is saying is that, in view of the authority of Moses, When they teach Moses’s Law, do that; when they live contrary to God’s heart, don’t copy them. Jesus never abolished the Law, but fulfilled it, and his ministry was always about bringing people into a true understanding of what it meant to follow God, to obey God, to love God.

Reject the things that the Pharisees do themselves. He gives this list of things they do, where they have essentially added extrabiblical rules and regulations that they enforced with shameless inconsistency as it regarded themselves.

They put on a show outwardly, adorning themselves with these accessories that make them look pious and holy. They sit in the visible places to be seen as pious and holy. They love their honorific titles. They “play the part”, but they do not truly live out the truth of God’s law. They are anything but pious and holy.

Jesus urges the crowd to reject titles, to reject fame, to reject anything that will elevate them above others, anything that will glorify self. You do not need to be called teacher, because you have a Teacher. God. You do not need to call these priests father, because you have a Father. God. You have an instructor before you, the Christ!

This is fully in line with Jesus’ teaching we’ve seen throughout this book. Reject arrogance and pride. Do not boast in yourselves, boast in God, he says!

And in verses 11 and 12, Jesus says something he has said before.

Matthew 23:11–12 ESV

11 The greatest among you shall be your servant. 12 Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.

He hasn’t even directly addressed the Pharisees yet here, but this is a subtle jab to them. They think themselves great, they exalt themselves. So, they will fall. Anyone who does the same, will fall. But anyone who humbles himself as a servant, he will be lifted up by God.

Now, Jesus turns his attention to the scribes and Pharisees, as we get to the first of the woes, and the first of the charges of hypocrisy.

Jesus condemns hypocritical faith. - v.13-36

Matthew 23:13–15 ESV

13 “But woe to you, scribes and Pharisees, hypocrites! For you shut the kingdom of heaven in people’s faces. For you neither enter yourselves nor allow those who would enter to go in. 15 Woe to you, scribes and Pharisees, hypocrites! For you travel across sea and land to make a single proselyte, and when he becomes a proselyte, you make him twice as much a child of hell as yourselves.

Hypocrites teach man’s religion while pretending to teach God’s. -v.13-15

Jesus condemns the Pharisees for claiming to have the knowledge of God and his Word, yet failing to actually provide it to the people through their teachings. They have traded the Law of God for the Law of the Pharisees, and this is effectively cutting people off from knowing God and living faithfully to him. These men were trusted with the authority and responsibility to shepherd God’s people, but they merely sought to build themselves and their own religious powers up. They will seek to make converts to Second Temple Judaism, but they are not bringing people into the kingdom of God. Instead, their selfish, sinful efforts are preparing people for destruction and eternal punishment in hell. Hypocrisy can actually block the doors to God’s kingdom.

Now Jesus exposes another layer: hypocrisy doesn’t just mislead others; it twists God’s law to justify our own sin.

Matthew 23:16–22 ESV

16 “Woe to you, blind guides, who say, ‘If anyone swears by the temple, it is nothing, but if anyone swears by the gold of the temple, he is bound by his oath.’ 17 You blind fools! For which is greater, the gold or the temple that has made the gold sacred? 18 And you say, ‘If anyone swears by the altar, it is nothing, but if anyone swears by the gift that is on the altar, he is bound by his oath.’ 19 You blind men! For which is greater, the gift or the altar that makes the gift sacred? 20 So whoever swears by the altar swears by it and by everything on it. 21 And whoever swears by the temple swears by it and by him who dwells in it. 22 And whoever swears by heaven swears by the throne of God and by him who sits upon it.

Hypocrites find (or make) loopholes for their sin. - v.16-22

This is the one time he issues a woe with different phrasing. He accuses the Pharisees of being blind guides, because they are allegedly leading people to God when they themselves do not see or know him! They make these trivial distinctions about what makes an oath binding, while missing the whole point of oaths. Oaths were often made in God’s name (“as Yahweh lives”), so broken oaths were profaning the Lord, taking his name in vain. Remember that from the 10 Commandments?

Jesus has already doubled down on his view of oaths in Matthew 5 with the Sermon on the Mount. Don’t swear oaths, he says. Just let your yes be yes, and your no be no.

You should simply keep your word! Jesus is not a fan of oaths at all, because what binds us should be our willingness to honor God and do good. We should be a people who are good on our word, not because we made oaths, but because it is who we are. But the Pharisees miss this, and their attempts to create loopholes (swearing to the gold/offering instead of to the temple/altar) are so that they can break their word without breaking God’s law.

Exodus 29:37 ESV

37 Seven days you shall make atonement for the altar and consecrate it, and the altar shall be most holy. Whatever touches the altar shall become holy.

The gold and the offering on the altar are not special! It is the holiness of God, the holiness of his dwelling place, the holiness of his place of worship, that are special. So Jesus is saying that any oaths made to anything in the temple or part of the temple are STILL oaths made to God, in God’s name. So hold fast to your word. Be men and women whose “yes” or “no” actually means something.

Matthew 23:23–28 ESV

23 “Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cumin, and have neglected the weightier matters of the law: justice and mercy and faithfulness. These you ought to have done, without neglecting the others. 24 You blind guides, straining out a gnat and swallowing a camel! 25 “Woe to you, scribes and Pharisees, hypocrites! For you clean the outside of the cup and the plate, but inside they are full of greed and self-indulgence. 26 You blind Pharisee! First clean the inside of the cup and the plate, that the outside also may be clean. 27 “Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs, which outwardly appear beautiful, but within are full of dead people’s bones and all uncleanness. 28 So you also outwardly appear righteous to others, but within you are full of hypocrisy and lawlessness.

Hypocrites appear outwardly righteous but lack inward faithfulness. - v.23-28

In verses 23 and 24, Jesus is noting how the scribes and Pharisees will be as accurate as possible on the small details. They are meticulous in offering their tithe on even the smallest portion of their garden herbs. Why? Because it looks like they are incredibly faithful to the letter of the law. But, they miss the spirit of the law, which was what… justice, mercy, faithfulness! They are not just, they are not merciful, they are not faithful.

Obedience matters, 100%. This is why Jesus says they ought to have done these things. But what matters more is WHY we are being obedient. The Pharisees did not desire to please God, but to pretend to appear righteous.

We know from Paul’s letters to Timothy that the Ephesian church struggled a lot with false teachers. They were constantly battling wicked, false gospels. We also know from Revelation 2 that they got really good at correcting false teaching, really good at maintaining a right doctrine. Everything looked good on paper.

Remember, the first few chapters of Revelation are Jesus addressing specific churches through John. So Jesus is directly addressing the Ephesian church, and what does he say to them? Where does he find fault?

Revelation 2:4 ESV

4 But I have this against you, that you have abandoned the love you had at first.

They abandoned their love. They lost the true heart of why the sought to be obedient and protect true teaching.

In verses 25-26, Jesus is continuing that thread. They make themselves clean on the outside, but are filled with and stained by all manners of sin. They focus more on looking holy, on playing the part, than they do on actually trying to be clean and holy by walking in accordance with God’s word. Jesus talks about this back in Matthew 15:11-18

Matthew 15:18 ESV

But what comes out of the mouth proceeds from the heart, and this defiles a person.

If the heart is clean, then everything that flows forth from it, including our works, will be clean. If the heart is dirty, then everything that flows forth will also be dirty.

Then, in verses 27-28, Jesus hits again with a particularly damning charge. He says they are essentially DEAD INSIDE! At the time, they literally washed tombs to be this bright, pristine white color so it was clear that these were unclean places where dead bodies lay. These places looked shiny and clean BECAUSE of how dirty they were inside. It was a warning to stay away, because you would be made unclean if you entered or touched the tomb.

The Pharisees look shiny and clean with their works, but they are dead. They are filled with hypocrisy and lawlessness, Jesus says.

There’s a heart problem—beautiful on the outside, dead on the inside. It matters both that we do righteous things from a faithful heart. We don’t have time to dive into that, but read Ephesians and James, and you can see this harmony of good works produced from genuine faith.

Matthew 23:29–32 ESV

29 “Woe to you, scribes and Pharisees, hypocrites! For you build the tombs of the prophets and decorate the monuments of the righteous, 30 saying, ‘If we had lived in the days of our fathers, we would not have taken part with them in shedding the blood of the prophets.’ 31 Thus you witness against yourselves that you are sons of those who murdered the prophets. 32 Fill up, then, the measure of your fathers.

Matthew 23:33–36 ESV

33 You serpents, you brood of vipers, how are you to escape being sentenced to hell? 34 Therefore I send you prophets and wise men and scribes, some of whom you will kill and crucify, and some you will flog in your synagogues and persecute from town to town, 35 so that on you may come all the righteous blood shed on earth, from the blood of righteous Abel to the blood of Zechariah the son of Barachiah, whom you murdered between the sanctuary and the altar. 36 Truly, I say to you, all these things will come upon this generation.

Hypocrites follow in the hypocrisy of those who came before them. -v.29-32

Hypocrites are bound for judgment for their faithlessness. -v.33-361

The Pharisees decorate these monuments to the prophets, appearing as if they honor and revere what they did, declaring that they would not have rejected and killed these men like their ancestors did.

But Jesus says they are witnessing against their very own selves! From Abel to Zechariah, the evil, wicked sons of Satan will always week to reject and kill the righteous, the ones sent by God. They rejected John the Baptist! They are presently rejecting Jesus and conspiring to kill him! They are the very same as their fathers, but they are so blinded by their hypocrisy that they cannot even see their foolishness! They have sunken into the mire of the same hypocrisy of their fathers. It is not new, it is merely different. Same old, broken down car, just a new coat of paint.

So, Jesus tells them to fill up the measure of their fathers. That is, “Go ahead and finish what your ancestors started.” Jesus knew what was coming, and he was prophesying in this moment, inviting them to fulfill their purpose and condemn the final, true prophet of God. Jesus. Complete the full quota of your sins. Kill the very Son of God.

Doing this, they condemn themselves to hell. All the wrath stored up for them and their ancestors for their rejection of God, for their sins against the prophets, for their murders and vile deeds and wayward lawlessness. All of the judgment for that is coming for them, for that generation.

Now, we see Jesus’ conclusion.

Matthew 23:37–39 ESV

37 “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! 38 See, your house is left to you desolate. 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.’ ”

Jesus laments unbelief, and consigns hypocrites to their choice. -v.37-39

Imagine you’re Jesus, in this scenario. Imagine you’ve been working tirelessly for years, seeking to bring the good news of repentance and grace and salvation to your lost and spiritually dead people. Time and time again, you see so many amazing experiences where people listen to your words of truth, where people are healed by the power of God that dwells fully inside you, where people are genuinely changed, both Jew and Gentile! How amazing would that be? How joyous?

Imagine, however, every time you try to call the ones who claim your Father’s name, claim to know and represent your Father, into that very same repentance and faith, they reject you, debate you, seek for ways to destroy you. You offer them hope and forgiveness beneath your wings, but they are not willing.

I can imagine Jesus is so weary. I can imagine Jesus is frustrated at their sin, and simultaneously heartbroken for what will come to them. Jerusalem, and all she holds, have turned away from God and chosen the path of death. Their sin is as sweet and addictive as the most potent honey, but it is deadlier than any poison.

All it would take is a little humility, a little faith, to just come to Jesus and accept his help. But their pride is too strong. So they do not come to Jesus. He offers refuge, but they reject it. He laments over this.

Jesus quotes from Psalm 118:26 in this last verse. This was chanted by the people as he entered Jerusalem back in chapter 21. Why does he reference this psalm? He does so because he is telling them that he is removing himself from their presence, and they will only see him again when he returns, where he will judge the living and the dead. Jerusalem will welcome him, then, but for those who did not welcome him at first, they will be dashed against the rock that is Christ and condemned for their rejection of him.

Main Idea: Jesus recognizes and condemns hypocritical faith. Those who follow him, genuinely and humbly, will be saved from condemnation.

Conclusion

Let me ask you a question, and I want you to think on it for a second.

Where do you fit into all of this?

For each of us, we must consider which crowd we are part of. Disciples (imperfect followers), crowds (impressed, unsurrendered), or Pharisees (dead hypocrites)?

It is important for us to remember that hypocrisy is not the same as messing up. The problem for the Pharisees was not that the messed up, but that they pretended to be perfect keepers of the Law when they were anything but.

So many people lob insults at the church, saying it is filled with hypocrites. But I do not think this is fair. Sure, there are certainly hypocrites today, just as back then.

I think most genuine Christians do not claim to be perfect. We recognize when we make mistakes, or we at least listen, and repent, when someone else calls us out.

Let me encourage and affirm you: just because you may preach the gospel, and preach obedience, but then you still struggle with sin, that does not make you a hypocrite! That is Romans 7! The things I want to do, I do not do, and the things I do not want to do, I do!

That is the pinnacle of the Christian experience! Year by year, month by month, week by week, day by day, moment by moment, we are always wrestling with the truth we seek to live and the ways in which we fail to actually live it.

That’s why grace is so necessary. That’s why Paul says in Romans 7:20-25

Romans 7:24–25 ESV

24 Wretched man that I am! Who will deliver me from this body of death? 25 Thanks be to God through Jesus Christ our Lord! So then, I myself serve the law of God with my mind, but with my flesh I serve the law of sin.

This tension of sin and obedience leads us to ongoing repentance, not to shrugging at sin. The Pharisees hid and shrugged at their own sin. They pretended. We must not do that.

Jesus doesn’t want pretenders. He despises pretenders. He loves sinners. And he loves sinners who come to him, knowing they need help, and actually seek his help.

I know this can feel like a heavy sermon. Where is the hope for us?

Verse 37. Just as Jesus would gather the children of Jerusalem under his wings, if they were willing, so he will do for us, if we are willing.

Romans 8:1 ESV

There is therefore now no condemnation for those who are in Christ Jesus.

There is grace. But we have to recognize who God is, and who we are in light of him. We are but a humble people, chosen by God, and saved to live a life of love to him and to others.

So, if you struggle with feeling like a hypocrite, maybe its because you are! Repent of that! Or, maybe its because you actually care about being faithful to Jesus, and you are broken when you fail. Rest in Christ. Fear not, for Jesus has redeemed you. You are saved by works… just not your own.

So, most of us are probably not the Pharisees in this situation. But we must learn from their mistakes, learn from Jesus’ rebuke, and always seek to be humble, contrite, repentant, faithful to Jesus.