Matthew 23 - Eight Woes

The Tag Team on the Ropes

It is good to be with you again. If you have your Bibles, go ahead and turn to Matthew 23. We are going to cover the entire chapter together. For those who have been journeying with us, we have been in the Gospel of Matthew for a long time. We have broken this gospel into mini-series, and we are currently concluding a stretch called Rejected. The overarching reality is that Jesus, having presented Himself as the Savior of the world, was rejected by the religious leaders of His day.

Over the last couple of weeks, we have witnessed a strange biblical dynamic—what I called a biblical tag team. Four distinct religious factions, who could not even agree on where to get coffee together, united in their disdain for Jesus. You had the Pharisees, the Sadducees, the Herodians, and the scribes. The ancient proverb proved true: the enemy of my enemy is my friend. Despite their fierce theological and political divisions, they shared a common hostility toward Christ.

Last week, we saw the final tag made to a scribe—a lawyer of the Mosaic law. He asked Jesus which of the 613 commandments in the Old Testament was the greatest. Jesus drew from Deuteronomy 6 and Leviticus 19, weaving them together into a unified answer: love the Lord your God with all your heart, soul, mind, and strength, and love your neighbor as yourself.

Matthew 22:37-39 (NASB)

And He said to him, ’‘YOU SHALL LOVE THE LORD YOUR GOD WITH ALL YOUR HEART, AND WITH ALL YOUR SOUL, AND WITH ALL YOUR MIND.’ ’This is the great and foremost commandment. ’The second is like it, ‘YOU SHALL LOVE YOUR NEIGHBOR AS YOURSELF.’

We highlighted that genuine love for God was vastly different from what people observed in their religious leadership. The leaders modeled what we termed “above the line” religion—loving God merely with the mind and physical strength. Their devotion was reduced to a cold formula: know the rules and execute the actions. Knowing Scripture and obeying God is not inherently bad, but on its own, it is profoundly insufficient. Living above the line is like running on a religious treadmill. It is exhausting, unproductive, and ultimately destructive.

Jesus invited them to build “below the line”—a deep reservoir of heart and soul devotion, engaging their deepest affections and walking in the mystery of the Spirit. Love for God and love for neighbor are intimately intertwined. If you struggle to love your neighbor, it is not merely a social problem; it is symptomatic of a vertical disconnect. Love for neighbor is the direct overflow of love for God. When our relationship with God is robust, joyful, and life-giving, loving others becomes natural.

If your heart does not break for those around you who do not know Jesus, if you look at injustice and feel indifferent, if you are unstirred by the needs in our community, you do not just have a love-of-neighbor problem. You likely have a love-of-God problem. When we truly love God, He realigns our affections and moves us into action.

At the end of chapter 22, after enduring round after round of hostile questions, Jesus went on the offensive. He put His opponents on the ropes.

Matthew 22:41-46 (NASB)

Now while the Pharisees were gathered together, Jesus asked them a question: ‘What do you think about the Christ, whose son is He?’ They said to Him, ‘[The son] of David.’ He said to them, ’Then how does David in the Spirit call Him ‘Lord,’ saying, ’THE LORD SAID TO MY LORD, ’SIT AT MY RIGHT HAND, UNTIL I PUT YOUR ENEMIES BENEATH YOUR FEET ‘’? ’If David then calls Him ‘Lord,’ how is He his son?’ No one was able to answer Him a word, nor did anyone dare from that day on to ask Him another question.

He demonstrated that the Messiah was not merely an earthly descendant in David’s family tree, but David’s divine Lord. Verse 46 tells us His opponents were silenced. But Jesus did not stop there.

Unmasking the Performers

Chapter 23 is entirely Jesus on the offensive. If you have a red-letter Bible, you will see a massive sea of red text. Jesus begins landing blow after blow, and the religious leaders have zero response.

Look at who He addresses in verse 1. Jesus turns to the crowds and to His disciples. Picture the scene: the religious leaders are standing nearby, and Jesus points them out publicly.

Matthew 23:1-3 (NASB)

Then Jesus spoke to the crowds and to His disciples, saying: ’The scribes and the Pharisees have seated themselves in the chair of Moses; therefore all that they tell you, do and observe, but do not do according to their deeds; for they say [things] and do not do [them].

He tells the crowd that the scribes and Pharisees have seated themselves in the seat of Moses. In ancient synagogues, the place of highest honor was known as Moses’ seat—similar to elevating prominent dignitaries on a stage. Jesus says to respect their teaching when it aligns with God’s law, but warns: do not imitate their lives, because they preach what they refuse to practice.

Matthew 23:4-7 (NASB)

’They tie up heavy burdens and lay them on men’s shoulders, but they themselves are unwilling to move them with [so much as] a finger. ’But they do all their deeds to be noticed by men; for they broaden their phylacteries and lengthen the tassels [of their garments]. ’They love the place of honor at banquets and the chief seats in the synagogues, and respectful greetings in the market places, and being called Rabbi by men.

They tie up crushing burdens and lay them on people’s shoulders, yet will not lift a single finger to help. Every religious act they perform is designed strictly for public applause. They broaden their phylacteries—the small leather boxes containing Scripture straps worn on the forehead and arm—making them larger to look more pious. They lengthen the ceremonial tassels on their prayer garments. They covet the seats of honor at banquets, the chief seats in the synagogues, respectful public greetings, and prestigious titles like “Rabbi.”

Jesus exposes their motive: their religion is entirely about self-preservation, prestige, and power, devoid of genuine love for God or people. He immediately instructs His followers to adopt a radically different posture.

Matthew 23:8-12 (NASB)

’But do not be called Rabbi; for One is your Teacher, and you are all brothers. ’Do not call [anyone] on earth your father; for One is your Father, He who is in heaven. ’Do not be called leaders; for One is your Leader, [that is], Christ. ’But the greatest among you shall be your servant. ’Whoever exalts himself shall be humbled; and whoever humbles himself shall be exalted.

He tells them not to chase honorary titles or demand elevating status. We have one Teacher, one Father, and one Leader—Christ. The greatest among us must be a servant. Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.

The Eight Woes

Beginning in verse 13, Jesus unleashes eight consecutive prophetic indictments known as the “woes.” These statements represent eight unrelenting strikes against superficial religion.

When we read the word “woe,” it sounds archaic. In biblical terms, a woe is a declaration of impending disaster, deep sorrow, and severe distress. The Message translation captures the raw weight well: “I’ve had it with you. You are hopeless, you scribes and Pharisees.”

Let us walk through these eight woes.

1. Shutting the Kingdom Door

Matthew 23:13 (NASB)

’But woe to you, scribes and Pharisees, hypocrites, because you shut off the kingdom of heaven from people; for you do not enter in yourselves, nor do you allow those who are entering to go in.

Jesus calls them hypocrites—a Greek theatrical term for actors wearing masks. The first woe addresses their rejection of the gospel. They refused to receive Jesus as Messiah and actively barred others from entering God’s kingdom.

2. Exploiting Religion for Personal Gain

Matthew 23:14 (NASB)

[‘Woe to you, scribes and Pharisees, hypocrites, because you devour widows’ houses, and for a pretense you make long prayers; therefore you will receive greater condemnation].

They used spiritual pretense to enrich themselves, even exploiting vulnerable widows under the guise of long, pious prayers. Their religious platform was a tool for personal profit rather than humble service.

3. Multiplying Destruction

Matthew 23:15 (NASB)

’Woe to you, scribes and Pharisees, hypocrites, because you travel around on sea and land to make one proselyte; and when he becomes one, you make him twice as much a son of hell as yourselves.

They traveled across land and sea to win a single convert, but instead of leading that person to life in God, they discipled them into legalism, making them twice as much a child of hell as themselves.

4. Constructing Loopholes

Matthew 23:16-22 (NASB)

’Woe to you, blind guides, who say, ‘Whoever swears by the temple, [that] is nothing; but whoever swears by the gold of the temple is obligated.’ ’You fools and blind men! Which is more important, the gold or the temple that sanctified the gold? ’And, ‘Whoever swears by the altar, [that] is nothing, but whoever swears by the offering on it, he is obligated.’ ’You blind men, which is more important, the offering, or the altar that sanctifies the offering? ’Therefore, whoever swears by the altar, swears [both] by the altar and by everything on it. ’And whoever swears by the temple, swears [both] by the temple and by Him who dwells within it. ’And whoever swears by heaven, swears [both] by the throne of God and by Him who sits upon it.

Jesus calls them blind guides. They engineered elaborate, man-made swearing systems to create moral loopholes—arguing that swearing by the temple meant nothing, but swearing by the gold of the temple was legally binding. They prioritized the material gift over the sacred God who sanctified the altar.

5. Majoring on the Minors

Matthew 23:23-24 (NASB)

’Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cummin, and have neglected the weightier provisions of the law: justice and mercy and faithfulness; but these are the things you should have done without neglecting the others. ’You blind guides, who strain out a gnat and swallow a camel!

They meticulously counted out tiny leaves of mint, dill, and cumin from their herb gardens to tithe exactly ten percent, while completely neglecting the central pillars of God’s character: justice, mercy, and faithfulness. Jesus mocks their absurdity: they strain out a tiny gnat from their drink while swallowing an entire camel whole.

6. External Cleansing, Internal Rot

Matthew 23:25-26 (NASB)

’Woe to you, scribes and Pharisees, hypocrites! For you clean the outside of the cup and of the dish, but inside they are full of robbery and self-indulgence. ’You blind Pharisee, first clean the inside of the cup and of the dish, so that the outside of it may become clean also.

They washed the outside of the cup and dish, obsessed with ritual purity, while inside they remained filled with greed and self-indulgence. Jesus demands that the inside be cleansed first so the outside can truly be clean.

7. Whitewashed Tombs

Matthew 23:27-28 (NASB)

’Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs which on the outside appear beautiful, but inside they are full of dead men’s bones and all uncleanness. ’So you, too, outwardly appear righteous to men, but inwardly you are full of hypocrisy and lawlessness.

Tombs were traditionally whitewashed with lime so travelers would not accidentally touch them and become ceremonially unclean. Outwardly, the tombs looked bright, clean, and pristine; inside, they held decaying bones. Jesus says their righteousness was merely cosmetic masking internal lawlessness.

8. Feigned Devotion and Hard Hearts

Matthew 23:29-36 (NASB)

’Woe to you, scribes and Pharisees, hypocrites! For you build the tombs of the prophets and adorn the monuments of the righteous, and say, ‘If we had been [living] in the days of our fathers, we would not have been partners with them in [shedding] the blood of the prophets.’ ’So you testify against yourselves, that you are sons of those who murdered the prophets. ’Fill up, then, the measure [of the guilt] of your fathers. ’You serpents, you brood of vipers, how will you escape the sentence of hell? ’Therefore, behold, I am sending you prophets and wise men and scribes; some of them you will kill and crucify, and some of them you will scourge in your synagogues, and persecute from city to city, so that upon you may fall [the guilt of] all the righteous blood shed on earth, from the blood of righteous Abel to the blood of Zechariah, the son of Berechiah, whom you murdered between the temple and the altar. ’Truly I say to you, all these things will come upon this generation.

They built elaborate monuments to past prophets, declaring arrogantly that had they lived in their ancestors’ day, they never would have shed innocent blood. Yet within forty-eight hours, they would crucify the very Son of God. Jesus identifies them as the true sons of those who murdered God’s messengers from Abel in Genesis to Zechariah in Chronicles—spanning the entire canon of Old Testament martyrs.

Genesis 4:8 (NASB)

Cain told Abel his brother. And it came about when they were in the field, that Cain rose up against Abel his brother and killed him.

2 Chronicles 24:20-22 (NASB)

Then the Spirit of God came on Zechariah the son of Jehoiada the priest; and he stood above the people and said to them, ’Thus God has said, ‘Why do you transgress the commandments of the LORD and do not prosper? Because you have forsaken the LORD, He has also forsaken you.’’ So they conspired against him and at the command of the king they stoned him to death in the court of the house of the LORD. Thus Joash the king did not remember the kindness which his father Jehoiada had shown him, but he murdered his son. And as he died he said, ‘May the LORD see and avenge!’

Jesus warned that the cumulative judgment for this persistent rebellion would fall squarely upon that generation.

The Mirror of Pharisaism

It is easy to read Matthew 23 and distance ourselves from the Pharisees, thinking how glad we are not to be like them. But if we are honest, we share far more in common with them than we care to admit.

Our modern culture is obsessed with external image. We craft carefully curated social media feeds, pursue flawless aesthetics, drive the right cars, wear the right clothes, and drop the right cultural references. We expend tremendous energy maintaining a spiritual and social facade, all while neglecting simple, secret devotion to Jesus.

As a pastor, this is an ongoing hazard for my own soul. I am naturally action-oriented, and it is easy to get caught up in performance, metrics, and people’s opinions. Every week, I am evaluated on my teaching. In human insecurity, it is tempting to care more about how a message is received than about staying intimately connected to the living God.

Scripture reminds us to guard our hearts diligently, because everything flows from within.

Proverbs 4:23 (NASB)

Watch over your heart with all diligence, For from it [flow] the springs of life.

Proverbs 27:19 (NASB)

As in water face [reflects] face, So the heart of man [reflects] man.

I can study, prepare, record videos, and lead gatherings with a cold heart, and almost nobody would know except God and me. That danger is not unique to vocational ministry; it confronts every one of us.

Do you feel the exhausting burden to perform? Do you carry shame when your reality fails to match your public image? Have the spiritual disciplines—Bible reading, church attendance, or service—become mechanical duties rather than avenues of intimacy with Christ? The moment our religious habits replace genuine love for God, we have embraced the way of the Pharisee.

The Heart of the King

Notice how Jesus concludes this chapter. He does not walk away in detached anger; He weeps over the city.

Matthew 23:37-39 (NASB)

’Jerusalem, Jerusalem, who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together, the way a hen gathers her chicks under her wings, and you were unwilling. ’Behold, your house is being left to you desolate! ’For I say to you, from now on you will not see Me until you say, ‘BLESSED IS HE WHO COMES IN THE NAME OF THE LORD!’’

Jesus grieved over Jerusalem. He longed to gather her children together as a hen shelters her chicks beneath her wings, but they were unwilling. Because they rejected their King, their house was left desolate.

Jesus then sets up a massive prophetic transition. He tells them they will not see Him again until they proclaim, “Blessed is He who comes in the name of the Lord”—pointing directly to His future glorious return. This dramatic declaration sets the stage for the Olivet Discourse in chapter 24, where Jesus details the end of the age, the great tribulation, and His ultimate second coming.

A Call to Repentance and Intimacy

The drift toward legalism rarely happens overnight. When people first come to faith in Christ, they are often full of passion and void of polish. They openly share the gospel, devour Scripture, and celebrate God’s grace. But over time, passion cools and polish takes over. We learn how to look the part, speak the language, and maintain external appearances while our hearts grow distant and hard.

Jesus delivered these sharp rebukes not to crush people, but to awaken them from the dead end of religion and draw them back into real intimacy with Himself.

If you recognize the marks of the Pharisees in your own heart—if you have pursued personal gain, elevated trivial rules above mercy, hidden behind an external facade, or allowed your spiritual life to become mechanical—the invitation today is to repent.

1 John 1:9 (NASB)

If we confess our sins, He is faithful and righteous to forgive us our sins and to cleanse us from all unrighteousness.

We are not defined by our past failures. Through the gospel, Jesus cleanses us from the inside out and restores our joy. Let us set aside religious performance and return to wholehearted devotion to Christ.

Closing Prayer

Father, thank You for Your Word and for the sobering clarity of Scripture. As we reflect on these warnings, search our hearts. Know our thoughts and reveal any hurtful way within us.

Psalms 139:23-24 (NASB)

Search me, O God, and know my heart; Try me and know my anxious thoughts; And see if there be any hurtful way in me, And lead me in the everlasting way.

Where our love has grown cold, awaken us. Where we have traded genuine intimacy for empty religious routine, grant us the grace to repent. Refresh our souls with Your presence. As we share communion together across our neighborhoods, remind us of the broken body and shed blood of Jesus, which alone makes us clean. We pray this in Jesus’ name. Amen.