The King's Indictment: Gospel Woes and Whitewashed Tombs
Introduction: The Roar of the Lamb
We live in an age that has domesticated Jesus. Our modern conception of Him is a sanitized, soft-spoken therapist who would never raise His voice, never offend anyone, and whose primary message is a sort of generic "be nice." This is a Jesus made in our own effeminate image. But the Jesus of the Scriptures, the Lion of the tribe of Judah, is not safe. He is good, but He is not safe. And nowhere is this more apparent than in Matthew 23.
After patiently answering the trick questions of the religious establishment, the Sadducees, the Herodians, and the Pharisees, Jesus now turns the tables. The time for parrying their attacks is over. The King is now pressing His own charges. This chapter is a blistering, unrelenting, sevenfold declaration of woe upon the spiritual leaders of Israel. This is not a petulant outburst; it is a formal, covenantal lawsuit. It is the divine indictment before the sentence is passed.
We must understand the nature of these woes. They are the inverse of the Beatitudes in chapter 5. The Beatitudes begin with "Blessed are..." and describe the citizens of the kingdom. The Woes begin with "Woe to you..." and describe the enemies of the kingdom. A woe is not a vindictive curse; it is a cry of profound sorrow and a declaration of impending judgment. It is the cry of a physician telling a man who refuses treatment that his disease will be terminal. Jesus is not just angry; His heart is breaking over the spiritual ruin these men are causing. They were the appointed shepherds, and they had become wolves. They were the gatekeepers, and they had locked the doors. They were the guides, and they were leading people off a cliff.
This passage is a divine diagnostic of a corrupt and dying religious system. And we must not read it as mere ancient history. The spirit of the Pharisee is perennial. It is a constant temptation for any religious institution, including our own. We must therefore come to this text with the prayer, "Lord, is it I?" Let us examine the charges, for they are as relevant in our day as they were in His.
The Text
"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. [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.] 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. Woe to you, blind guides... You serpents, you brood of vipers, how will you escape the sentence of hell? ...Truly I say to you, all these things will come upon this generation."
(Matthew 23:13-36 LSB)
The Core Charge: Hypocrites and Blind Guides
Before we walk through the specific woes, we must see the two charges that Jesus levels again and again: "hypocrites" and "blind guides." The word for hypocrite comes from the Greek stage; it means an actor, one who wears a mask. Their entire religious life was a performance. They were playing the part of righteous men, but it was a sham. They were concerned with their reputation before men, not their standing before God. Their piety was a costume.
And because they were actors, they were necessarily blind. A man who is pretending to see cannot be taught how to see. Their blindness was a willful, culpable blindness. They had the Scriptures, the prophecies, the very Son of God standing before them, and they refused to see. Their intricate religious system, which was supposed to be a lens to see God more clearly, had become a blindfold. This combination of hypocrisy and blindness is lethal. It not only damns the hypocrite, but it makes him a danger to everyone he influences.
Woes of Destruction: Damning Others (vv. 13-15)
The first set of woes focuses on the catastrophic spiritual damage these leaders inflicted on others.
"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." (Matthew 23:13 LSB)
This is the ultimate sin of a spiritual leader. They were given the keys to the kingdom, the Word of God, but they used those keys to lock the door. They buried the plain meaning of the Scriptures under a mountain of man-made traditions. They presented a vision of God that was impossible to please and a path to righteousness that was impossible to walk. When common people, the tax collectors and prostitutes, began to press into the kingdom through the preaching of John and Jesus, the Pharisees stood in the doorway and blocked them. They would not enter the kingdom of grace themselves, and they did everything in their power to prevent others from entering.
Verse 15 reveals the horror of their evangelism:
"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." (Matthew 23:15 LSB)
They were zealous missionaries. They were willing to cross land and sea to make a convert. But what were they converting people to? Not to a living faith in Yahweh, but to their dead, hypocritical, soul-crushing system. A convert to a false system is often more zealous and rigid than his teachers. They took a Gentile who was seeking God and inoculated him against true grace. They turned him into a "son of hell," meaning one whose character is defined by hellishness. Their evangelism was a spiritual cloning program, producing Pharisees in their own image. It is a terrifying thing to be zealous for a lie.
Woes of Distortion: Corrupting the Law (vv. 16-24)
The next set of woes exposes how they twisted the very law of God to serve their own ends.
"Woe to you, blind guides, who say, 'Whoever swears by the sanctuary, that is nothing; but whoever swears by the gold of the sanctuary is obligated.' You fools and blind men! For which is more important, the gold or the sanctuary that sanctified the gold?" (Matthew 23:16-17 LSB)
This is casuistry of the highest order. They had created a complex system of oath-making that allowed them to lie while maintaining an appearance of piety. They made fine distinctions, swearing by the temple versus swearing by the gold of the temple, to create loopholes for their own dishonesty. Jesus demolishes their foolishness with simple logic. What makes the gold holy? The temple. What makes the offering holy? The altar. Their system was an inversion of reality. They elevated the gift above the altar, the gold above the temple, in order to control which promises they had to keep. In doing so, they forgot that every oath is ultimately made before God. An oath is a sacred thing, and they had turned it into a lawyer's game.
This distortion is summarized in their approach to tithing:
"Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cumin, 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 but swallow a camel!" (Matthew 23:23-24 LSB)
Their sin was not their meticulousness. Jesus says they should have continued to tithe their garden herbs. The sin was their grotesque sense of proportion. They were hyper-focused on the most minor applications of the ceremonial law while completely ignoring the moral heart of the law. They would measure out their spice rack for God, but they would devour a widow's house. They would strain their water to ensure they did not accidentally swallow a tiny, unclean insect, a gnat. But they would happily gulp down a camel, a massive, unclean animal. This is a picture of moral insanity. They majored in the minors and minored in the majors. They were obsessed with the footnotes of the law and ignored the headlines.
Woes of Deception: Internal Corruption (vv. 25-28)
The final woes turn from their external actions to their internal state. The problem is not just what they do, but who they are.
"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." (Matthew 23:25-26 LSB)
This is the essence of hypocrisy. They were obsessed with external, ceremonial cleanliness. But inside, their hearts were filthy with greed and a lack of self-control. Jesus's solution is radical. He does not say, "Try to balance the inside and the outside." He says, "Clean the inside first." True righteousness is an inside-out job. When God regenerates a heart, a new nature is born. And from that clean heart, clean actions will naturally flow. The Pharisees' project was to polish the outside of a cup full of filth, which is absurd. The gospel project is for God to miraculously clean the inside, which results in a clean outside as a matter of course.
Jesus then uses an even more stark image:
"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." (Matthew 23:27 LSB)
In that culture, tombs were painted white so that people would not accidentally touch them and become ceremonially unclean. They looked clean, bright, and beautiful from a distance. But everyone knew what was inside: death, decay, and corruption. This was the Pharisees' spiritual state. Outwardly, they were the models of righteousness. Inwardly, they were spiritually dead, full of the uncleanness of sin. They were walking sepulchers.
The Climax: The Measure of Guilt (vv. 29-36)
Jesus concludes His indictment with a terrifying historical pronouncement.
"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 bear witness against yourselves, that you are sons of those who murdered the prophets." (Matthew 23:29-31 LSB)
They honored the dead prophets while plotting to kill the living ones, including the Lord of the prophets Himself. They piously condemned the sins of their ancestors while replicating them perfectly. By acknowledging their fathers' guilt and continuing in the same spirit, they were testifying against themselves. Then comes the chilling command: "Fill up, then, the measure of the guilt of your fathers." God, in His sovereignty, allows sin to run its course, to ripen until the time of judgment. Their generation was to be the one that filled the cup of Israel's covenant rebellion to the brim by murdering the Messiah.
And the sentence would fall swiftly.
"You serpents, you brood of vipers, how will you escape the sentence of hell? ... Truly I say to you, all these things will come upon this generation." (Matthew 23:33, 36 LSB)
Jesus calls them what John the Baptist called them: a brood of vipers, the offspring of the ancient serpent. And He declares that the accumulated guilt of all the righteous blood shed, from Abel to Zechariah, would come upon "this generation." This is not a reference to the final judgment at the end of time. Jesus is speaking about a historical, temporal judgment. He is prophesying the utter destruction of Jerusalem and its temple, which occurred within forty years, in A.D. 70. That event was the final, decisive end of the Old Covenant order. It was God's verdict on the apostate leadership of Israel. And it came upon that very generation, just as Jesus said it would.
Conclusion: The Only Escape
The question Jesus asks is the question that should echo in our souls: "how will you escape the sentence of hell?" The Pharisee has no answer. His only tool is self-righteousness, which is the very heart of the disease. You cannot escape hell by trying to be a better Pharisee.
The modern church is filled with the spirit of the Pharisee. We have those who strain out the gnat of a particular political view but swallow the camel of rampant sexual immorality. We have those who clean the outside of the cup with their polished worship services and impressive buildings, but whose hearts are full of greed and a lust for power. We have those who build monuments to the reformers of old while persecuting the voices calling for reformation today.
The only escape is to abandon the entire project of self-justification. It is to confess that we are the whitewashed tomb, full of dead men's bones. It is to stop pretending, to take off the mask, and to plead for a mercy we do not deserve. The good news is that the one who pronounces these woes is also the one who provides the escape. Jesus Christ did not just diagnose the disease; He drank the poison. He took the full measure of our guilt upon Himself at the cross. He cleans the inside of the cup by His blood and by His Spirit.
Do not be a son of the Pharisees. Be a son of God. Flee from your own righteousness, which is a filthy rag, and cling to the righteousness of Jesus Christ, which is a royal robe. That is the only way to escape the judgment to come.