Commentary - Matthew 23:13-36

Bird's-eye view

In this blistering section of Matthew's Gospel, the Lord Jesus Christ concludes His public ministry by pronouncing a series of seven, or arguably eight, woes upon the scribes and Pharisees. This is not a petulant outburst; it is a formal, covenantal lawsuit delivered by the King Himself. Having silenced all His opponents with unanswerable wisdom, Jesus now turns the tables and becomes the prosecutor. He systematically dismantles their entire religious system, exposing it as a hollow sham of hypocrisy. The central charge is that their religion is entirely external, concerned with appearances, while their hearts are full of corruption, greed, and lawlessness. The passage climaxes with a prophecy of judgment that will fall upon that very generation for their cumulative, covenantal guilt in rejecting God's messengers, a judgment that found its historical fulfillment in the catastrophic destruction of Jerusalem in A.D. 70.

Each woe follows a pattern: the denunciation ("Woe to you..."), the identification of the culprits ("scribes and Pharisees, hypocrites"), and the specific reason for the woe. Jesus exposes their work as actively hindering the kingdom, their evangelism as damning, their theology as nonsensical casuistry, their piety as trivial, their purity as superficial, and their reverence for the past as a mask for their present murderous intent. This is the righteous wrath of the Lamb, and it serves as a permanent warning to the church against any form of religion that substitutes human tradition and external performance for heart-felt repentance and faith in Christ.

Outline

Context In Matthew

Matthew 23 functions as the climactic conclusion to Jesus' public confrontation with the religious leadership of Israel. This chapter directly follows the series of challenges to Jesus' authority in Matthew 21 and 22, where He bested the chief priests, elders, Pharisees, Sadducees, and Herodians in debate. Having established His authority beyond question, He now exercises it in judgment. The chapter begins with a warning to the crowds and His disciples about the hypocrisy of the scribes and Pharisees (Matt 23:1-12) before launching into the woes themselves. This entire section serves as a prelude to the Olivet Discourse (Matt 24-25), where Jesus will prophesy the destruction of the temple and the city of Jerusalem. The woes of chapter 23 provide the moral and covenantal basis for the physical destruction prophesied in chapter 24. It is the final, public sermon of the King before He turns to prepare His disciples for His impending death, resurrection, and the subsequent judgment on the old covenant order.

Key Issues

The Woes of the Covenant King

When we hear the word "woe," our modern sensibilities might interpret it as a simple expression of sorrow or pity, as in "Woe is me." But that is not what is happening here. The Greek word ouai, used here by Jesus, is a formal declaration of judgment. It is the announcement of impending doom, a covenantal curse pronounced by a rightful authority. This is not the language of a frustrated teacher; it is the language of a king and a judge.

Throughout the Old Testament, the prophets of God pronounced woes upon unfaithful Israel and upon pagan nations (e.g., Isa 5:8-23; Hab 2:6-19). These were not merely predictions; they were authoritative declarations that carried the weight of God's own verdict. When Jesus stands in the temple courts and says, "Woe to you," He is stepping into that prophetic role, but as something far greater than a prophet. He is the God of the prophets, the Lord of the covenant, pronouncing sentence upon those who have broken that covenant. The structure of these woes is that of a formal indictment. He is the prosecuting attorney, the judge, and the king, all in one, and He is laying out the legal basis for the judgment that is about to fall.

Verse by Verse Commentary

13 “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.

The first woe strikes at the very heart of their failure as religious leaders. Their primary job was to be gatekeepers of the kingdom, to teach the law in such a way that people would be led to God. But Jesus says they do the exact opposite. They are like a man standing in a doorway, refusing to go in, but also blocking the entrance with his body so that no one else can get in either. Their system of righteousness, based on meticulous rule-keeping and man-made traditions, was a barrier to the kingdom. It presented a false path to God that no one could actually walk, and it obscured the true path of repentance and faith. True religion opens the door; their hypocrisy slammed it shut and bolted it.

14 [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.]

While this verse is not present in the earliest and best manuscripts of Matthew, it is found in Mark and Luke and certainly reflects the teaching of Jesus. The principle is sound. It combines the sin of greed with the sin of false piety. They used their religious reputation to exploit the most vulnerable members of society, widows, likely by mishandling their estates as trustees. To cover this rapacious greed, they made a great show of public prayer. The longer the prayer, the holier they appeared, and the deeper the deception. Jesus says this combination of predation and piety earns them a greater condemnation. God's judgment is not a one-size-fits-all affair; it is perfectly just, and exploiting the vulnerable under the cloak of religion is a particularly heinous offense.

15 “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.

This is a stunning indictment of their missionary zeal. We might think that zeal for converts is always a good thing, but Jesus says their evangelism is actually damning. They would go to extraordinary lengths to persuade a Gentile to convert to Judaism. But what were they converting him to? Not to a living faith in Yahweh, but to their dead, hypocritical, legalistic system. The convert, having thrown himself wholeheartedly into this new religion, would often become even more zealous and rigid than his teachers. He was not brought into the kingdom of God; he was made a "son of hell," a child characterized by the nature of hell itself. He was made twice as bad because he combined the fresh zeal of a convert with the corrupt theology of the Pharisees. This is a sober warning that evangelism which brings people into a false system is worse than no evangelism at all.

16-17 “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?

Here Jesus moves from their hypocrisy to their casuistry, their clever but corrupt theological reasoning. They had developed a complex system for oaths, distinguishing between which ones were "binding" and which were not. This was a way to appear truthful while creating loopholes for dishonesty. They taught that an oath by the temple itself was non-binding, but an oath by the gold dedicated to the temple was. Jesus exposes the foolishness of this with a simple question. What makes the gold holy? The temple does. The greater sanctifies the lesser. To elevate the gift above the altar, the decoration above the divine institution, is utter blindness. It shows a heart that is impressed by glitter and wealth, but unimpressed by the presence of God which the temple represented.

18-19 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?

He provides a second, parallel example. They taught that swearing by the altar meant nothing, but swearing by the sacrifice on the altar was binding. Again, Jesus calls them blind and applies the same logic. The altar is what makes the gift a holy offering to God. The altar is greater than the gift. Their system was inverted; it was a theology of utter nonsense designed to facilitate lies.

20-22 Therefore, whoever swears by the altar, swears both by the altar and by everything on it. And whoever swears by the sanctuary, swears both by the sanctuary 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 concludes His lesson on oaths by sweeping away all their petty distinctions. You cannot separate a thing from its ultimate source of meaning. An oath by the altar implicitly includes the sacrifice on it. An oath by the temple implicitly includes the God who dwells there. And an oath by heaven implicitly calls upon God, whose throne heaven is. The point is that all speech is before the face of God. A man of integrity does not need oaths, his "yes" is yes (Matt 5:37). But if you do make an oath, you cannot play games. You are calling on God as your witness, no matter what verbal gymnastics you employ.

23-24 “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!

This woe addresses their distorted priorities. They were incredibly scrupulous about the minor details of the law, even tithing the tiny herbs from their gardens, which the law did not explicitly require. Jesus does not condemn their meticulousness; He says, "these are the things you should have done." Tithing is good. But their focus on the minutiae was a smokescreen to hide their neglect of the very heart of the law: justice, mercy, and faithfulness. These are the "weightier" matters. They were like a man who carefully filters his drinking water to remove a tiny gnat (an unclean insect), but then proceeds to gulp down a camel (a very large unclean animal). The image is absurd and comical, highlighting the grotesque nature of their spiritual blindness. They majored in the minors and failed the final exam.

25-26 “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.

The sixth woe returns to the theme of external purity versus internal corruption. Their religion was all about appearances. They were like someone who diligently washes the outside of a cup but leaves the inside filthy, caked with the residue of what it contains. And what did their cup contain? The fruit of robbery and self-indulgence. Their inner life, their heart, was corrupt. Jesus' solution is simple and profound. True righteousness works from the inside out. Clean the heart first. When a man is regenerated by the Spirit of God, when his desires are transformed, then his outward actions will naturally become clean as well. The Pharisees had it backwards; they thought that by polishing the outside, they could somehow make the inside clean. This is the essence of all legalistic, self-righteous religion.

27-28 “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. In this way, you also outwardly appear righteous to men, but inwardly you are full of hypocrisy and lawlessness.

This is perhaps the most searing and memorable of the woes. Tombs were whitewashed to make them highly visible, so people would not accidentally touch them and become ceremonially unclean. So on the outside, they looked clean and bright. But everyone knew what was inside: death, decay, and bones. Jesus says this is a perfect picture of the Pharisees. Outwardly, they appeared righteous, pious, and holy. But inwardly, their hearts were a spiritual graveyard, full of the stench of death, hypocrisy, and lawlessness. The beautiful exterior was a lie, concealing a hideous reality.

29-31 “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.

The final woe is the most climactic and damning. It deals with their relationship to redemptive history. They made a great show of honoring the prophets of old, building elaborate tombs for them. They piously claimed that they were nothing like their wicked forefathers who had murdered those prophets. But Jesus turns their own words against them with devastating logic. By calling the prophet-murderers their "fathers," they admit their lineage. And by their actions, they prove they are true sons of their fathers, not just by blood but by character. Their rejection of John the Baptist and of Jesus Himself proved they had the same murderous spirit. Honoring dead prophets is easy and costs nothing. Honoring a living prophet who confronts your sin is another matter entirely.

32-33 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?

This is the terrifying sentence. Jesus speaks with divine, sovereign irony. "Go ahead," He says, "finish the job. Your fathers started the rebellion; you bring it to its climax." The sin of the nation had been accumulating for centuries, and this generation, by rejecting and killing the Son of God, was about to fill the cup of God's wrath to the brim. He drops all pretense and addresses them with the same language John the Baptist used: serpents, brood of vipers. This identifies them with the ancient serpent of Genesis 3. Their father is the devil. And their destiny is the sentence of hell, or Gehenna, the place of fiery judgment. The question is rhetorical; there is no escape for them on their current path.

34-36 “On account of this, 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 flog 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 sanctuary and the altar. Truly I say to you, all these things will come upon this generation.

Jesus, speaking as the sovereign Lord of the church, declares that He will send His apostles and evangelists ("prophets and wise men and scribes") to them. And true to form, the leaders will reject, persecute, and murder them. This final act of rebellion will be the tipping point. It will cause the accumulated, corporate, covenantal guilt of all history's rebellion to come crashing down upon that specific generation. The list of martyrs is representative, stretching from Abel, the first martyr in Genesis, to Zechariah, a martyred priest near the end of the Old Testament canon's historical narrative. The key to this whole passage is the final, unambiguous statement: "Truly I say to you, all these things will come upon this generation." Jesus is not speaking of a far-future event. He is speaking of a historical judgment that would befall those people within their lifetimes, which is precisely what happened in the Roman destruction of Jerusalem in A.D. 70. That event was the final verdict of the covenant lawsuit Jesus prosecutes in this chapter.

Application

The woes of Matthew 23 are not just a historical record of a dispute between Jesus and some first-century Jewish leaders. They are a permanent and necessary warning for the Church in every age. The pharisaical spirit is a perennial temptation for religious people. It is the temptation to substitute the external for the internal, the traditional for the true, and the performance for the person.

We must ask ourselves: Are we more concerned with what people think of us than with what God knows of us? Do we have a zeal for our brand of Christianity that makes converts to our tribe rather than disciples of Jesus? Are we masters of theological hair-splitting that allows us to justify our sins? Do we focus on secondary issues of piety while neglecting justice for the oppressed, mercy for the broken, and faithfulness to our word? Is our spiritual life about polishing the exterior, or is it about the hard, daily work of mortifying the sin that dwells within our hearts?

The only antidote to the hypocrisy of the Pharisees is the gospel of grace. They believed they could be clean on the outside by their own efforts. The gospel tells us we are filthy inside and out, and our only hope is to be washed clean by the blood of another. Jesus did not come as a whitewashed tomb, righteous on the outside and corrupt within. He was pure through and through, and on the cross He took all our internal filth and corruption upon Himself. He became the ultimate "unclean thing" so that we might become the righteousness of God. True Christianity begins not with cleaning the cup, but with confessing that our cup is full of poison and begging the Physician to give us a new heart and a new spirit.