Matthew Chapter 23
Woes to the Scribes and the Pharisees
A. Jesus Rebukes the Scribes and Pharisees
1. Matthew 23:1–4 — They Lay Oppressive Burdens on Others
"Then Jesus spoke to the multitudes and to His disciples, saying: 'The scribes and the Pharisees sit in Moses’ seat. Therefore whatever they tell you to observe, that observe and do, but do not do according to their works; for they say, and do not do. For they bind heavy burdens, hard to bear, and lay them on men’s shoulders; but they themselves will not move them with one of their fingers.'" (Matthew 23:1–4, NKJV)
Jesus turns from confronting His enemies directly to warning the crowd and His disciples about the spiritual danger posed by their hypocrisy. Although the scribes and Pharisees held positions of authority—"Moses’ seat" symbolized teaching authority in the synagogue—they did not live according to the Law themselves. They taught righteousness but lived in contradiction to it. Jesus clearly differentiates between right teaching and wrong living. He instructs the people to do what they say when aligned with the Law, but not to follow their example.
This distinction remains vital in every generation: respect the authority of Scripture, not the hypocrisy of leaders who fail to live by it. As Paul said in Romans 2:21–23: "You, therefore, who teach another, do you not teach yourself? You who preach that a man should not steal, do you steal?... You who make your boast in the law, do you dishonor God through breaking the law?"
Jesus exposes their legalistic mentality: "they bind heavy burdens, hard to bear." This speaks of their endless regulations and oral traditions that were added to God’s Law, becoming a crushing weight that no one could carry—except perhaps outwardly, and even then, only through pretense. Jesus, by contrast, says in Matthew 11:30, "For My yoke is easy and My burden is light."
This was a condemnation of man-made religion—rules without relationship, external conformity without internal transformation. Peter, addressing a similar issue in the early Church, said in Acts 15:10: "Now therefore, why do you test God by putting a yoke on the neck of the disciples which neither our fathers nor we were able to bear?"
2. Matthew 23:5–10 — They Live for the Praise of Men
"But all their works they do to be seen by men. They make their phylacteries broad and enlarge the borders of their garments. They love the best places at feasts, the best seats in the synagogues, greetings in the marketplaces, and to be called by men, 'Rabbi, Rabbi.' But you, do not be called 'Rabbi'; for One is your Teacher, the Christ, and you are all brethren. Do not call anyone on earth your father; for One is your Father, He who is in heaven. And do not be called teachers; for One is your Teacher, the Christ." (Matthew 23:5–10, NKJV)
The heart of the Pharisee is laid bare in this section—they seek glory from man, not from God. Jesus earlier warned in Matthew 6:1, "Take heed that you do not do your charitable deeds before men, to be seen by them. Otherwise, you have no reward from your Father in heaven." This same spirit infected every facet of their religious life. Whether in dress, seating, greetings, or titles—they cultivated image over substance.
Their “phylacteries” were outward displays of religiosity—small boxes containing passages of Scripture (Exodus 13:1–10; Deuteronomy 6:4–9; 11:13–21), bound on the forehead and arm. They were commanded in Deuteronomy 11:18: "Therefore you shall lay up these words of mine in your heart and in your soul, and bind them as a sign on your hand, and they shall be as frontlets between your eyes." What was meant to be a reminder of devotion to the Lord became a badge of spiritual pride. The same was true for the "borders of their garments," a reference to the tassels commanded in Numbers 15:38–39, meant to remind Israel of God’s commandments.
Their ambition was for recognition and reverence. Yet Jesus cuts this down by commanding humility and brotherhood. He says, “Do not be called ‘Rabbi’… do not call anyone on earth your father… do not be called teachers.” This is not a prohibition against roles of instruction or parenthood, but a rebuke of spiritual elitism and ecclesiastical pride.
Paul called himself a father in the faith (1 Corinthians 4:15), a teacher (2 Timothy 1:11), and referred to others as sons in the gospel (Philippians 2:22), but he did so without the self-exaltation that Jesus condemns here. The command is about motive: rejecting the craving for status and instead promoting Christ as the only true spiritual authority.
3. Matthew 23:11–12 — True Greatness Is Found in Humility
"But he who is greatest among you shall be your servant. And whoever exalts himself will be humbled, and he who humbles himself will be exalted." (Matthew 23:11–12, NKJV)
Jesus teaches a radical inversion of worldly values. Greatness is not in how many serve you but in how many you serve. This echoes what He taught in Matthew 20:26–28: "Yet it shall not be so among you; but whoever desires to become great among you, let him be your servant. And whoever desires to be first among you, let him be your slave—just as the Son of Man did not come to be served, but to serve, and to give His life a ransom for many."
This principle underpins all godly leadership. True greatness is found in sacrificial love, quiet service, and humility before God. This verse is not just a warning to Pharisees, but a principle for all Christians: if you promote yourself, God will humble you; but if you humble yourself, God will exalt you—in His time, and for His glory.
B. The Eight Woes to the Religious Leaders
These woes are the counterpart to the beatitudes in Matthew 5:3–11. Where the beatitudes promised blessing to the humble, the meek, the pure in heart, and the persecuted, these woes pronounce condemnation upon the proud, deceitful, and religiously manipulative. Jesus speaks as the divine Judge, not out of petty irritation, but from righteous wrath and holy justice. As in Isaiah chapter 5 verses 8 through 23 and Habakkuk chapter 2 verses 6 through 19, these woes follow the pattern of Old Testament prophets, indicting the leadership for obstructing God's truth.
1. Matthew 23:13 — Woe to Those Who Shut Up the Kingdom
“But woe to you, scribes and Pharisees, hypocrites! For you shut up the kingdom of heaven against men; for you neither go in yourselves, nor do you allow those who are entering to go in.” (Matthew 23:13, NKJV)
The word "hypocrites" (Greek: hypokritēs) was originally used to describe stage actors. Here, Jesus strips their religious masks and reveals that behind their robes and rituals was rebellion against God. Rather than opening the way to God, they shut it off—turning the Law into a system of works and traditions rather than pointing to the Messiah.
They refused to enter the kingdom themselves by rejecting Christ, and in so doing, discouraged others from entering. In essence, they were false gatekeepers. Malachi chapter 2 verse 7 says, “For the lips of a priest should keep knowledge, and people should seek the law from his mouth; for he is the messenger of the Lord of hosts.” But these men perverted their duty. They became spiritual saboteurs.
The condemnation echoes Matthew chapter 18 verse 6: “But whoever causes one of these little ones who believe in Me to sin, it would be better for him if a millstone were hung around his neck, and he were drowned in the depth of the sea.”
2. Matthew 23:14 — Woe to Those Who Exploit the Vulnerable
“Woe to you, scribes and Pharisees, hypocrites! For you devour widows’ houses, and for a pretense make long prayers. Therefore you will receive greater condemnation.” (Omitted in many manuscripts, but preserved in Mark 12:40 and Luke 20:47, NKJV)
Even though many ancient manuscripts omit this verse in Matthew, the rebuke itself is well-attested in the parallel Synoptic accounts. Jesus condemns the scribes and Pharisees for exploiting widows—those most vulnerable in society—under the guise of religious piety. They were fleecing the faithful while putting on a spiritual show.
They “devour widows’ houses” by coercion, false counsel, or manipulation—perhaps convincing widows to donate property for religious favor, then using it for selfish gain. It was religious extortion clothed in respectability.
They “for a pretense make long prayers.” These extended prayers were performances, carefully crafted to give the illusion of holiness while concealing corruption.
Jesus assures that “you will receive greater condemnation.” There are degrees of judgment in hell, just as there are rewards in heaven. Luke chapter 12 verse 47 says, “And that servant who knew his master’s will, and did not prepare himself or do according to his will, shall be beaten with many stripes.”
This verse is a solemn warning to all spiritual leaders: those who exploit the weak while pretending righteousness will not escape God's judgment.
3. Matthew 23:15 — Woe to Those Who Mislead Converts
“Woe to you, scribes and Pharisees, hypocrites! For you travel land and sea to win one proselyte, and when he is won, you make him twice as much a son of hell as yourselves.” (Matthew 23:15, NKJV)
The religious leaders were evangelistic—but not in truth. Their zeal did not prove godliness; rather, they were making converts to legalism, self-righteousness, and tradition instead of to faith in the living God. They went far and wide, but their message misled people and led them further from the truth.
Paul expresses a similar burden in Romans chapter 10 verse 2: “For I bear them witness that they have a zeal for God, but not according to knowledge.”
The word proselyte (Greek: proselutos) referred to a Gentile convert to Judaism who fully submitted to its rituals, including circumcision and temple ordinances. These converts often became more extreme than their teachers, as they tried to prove their new loyalty—thus becoming “twice as much a son of hell.”
The phrase “son of hell” (Greek: huios geennēs) literally means someone destined for Gehenna, the place of eternal punishment. Jesus declares that these men—who claimed to guide others to God—were actually leading them into destruction. This is a sobering indictment: false religion is not merely mistaken; it is damning.
This same warning applies today to cults and false teachers who distort the gospel. Galatians chapter 1 verses 8 through 9 says, “But even if we, or an angel from heaven, preach any other gospel to you than what we have preached to you, let him be accursed.”
4. Matthew 23:16–22 — Woe to the Blind Guides Who Use Deceptive Oaths
“Woe to you, blind guides, who say, ‘Whoever swears by the temple, it is nothing; but whoever swears by the gold of the temple, he is obliged to perform it.’ Fools and blind! For which is greater, the gold or the temple that sanctifies the gold? And, ‘Whoever swears by the altar, it is nothing; but whoever swears by the gift that is on it, he is obliged to perform it.’ Fools and blind! For which is greater, the gift or the altar that sanctifies the gift? Therefore he who swears by the altar, swears by it and by all things on it. He who swears by the temple, swears by it and by Him who dwells in it. And he who swears by heaven, swears by the throne of God and by Him who sits on it.” (Matthew 23:16–22, NKJV)
Jesus condemns the religious leaders for their manipulative use of oaths. In seeking to avoid invoking God's name directly (in obedience to Exodus chapter 20 verse 7, “You shall not take the name of the Lord your God in vain”), they constructed a dishonest system of vows, ranking some as binding and others as optional, depending on whether they included the “gold of the temple” or the “gift on the altar.”
This elaborate system allowed them to lie while maintaining a veneer of holiness. But Jesus rebukes the core issue—spiritual blindness and legalistic sophistry. They failed to grasp that it was the temple that sanctified the gold and the altar that sanctified the gift—not the other way around.
Jesus also reminds them of the divine witness involved in all oaths: to swear by the temple is to swear by God, “who dwells in it”; to swear by heaven is to swear “by the throne of God and by Him who sits on it.” Every oath is binding, because all truth ultimately belongs to and is measured by God.
This passage ties closely with Matthew chapter 5 verse 37: “But let your ‘Yes’ be ‘Yes,’ and your ‘No,’ ‘No.’ For whatever is more than these is from the evil one.”
5. Matthew 23:23–24 — Woe to Those Who Major on Minors and Ignore the Weightier Matters
“Woe to you, scribes and Pharisees, hypocrites! For you pay tithe of mint and anise and cummin, and have neglected the weightier matters of the law: justice and mercy and faith. These you ought to have done, without leaving the others undone. Blind guides, who strain out a gnat and swallow a camel!” (Matthew 23:23–24, NKJV)
These religious leaders were meticulous in tithing even the smallest of herbs—mint, anise, and cummin—yet they utterly neglected the foundational principles of God’s moral law: justice, mercy, and faith. While Jesus does not dismiss tithing (saying “these you ought to have done”), He rebukes their inverted priorities.
Micah chapter 6 verse 8 provides the core of what God requires: “He has shown you, O man, what is good; and what does the Lord require of you but to do justly, to love mercy, and to walk humbly with your God?”
Their legalism was superficial. They measured righteousness by external compliance rather than internal transformation. Jesus illustrates their hypocrisy with biting humor: they would strain out a gnat from their wine to remain ceremonially clean, yet they would swallow a camel—one of the largest unclean animals (Leviticus chapter 11 verse 4).
This exposes the danger of religious obsession with minutiae while missing the heart of God's Word. In modern terms, it's like obsessing over the font in your Bible app while ignoring the command to love your neighbor.
6. Matthew 23:25–26 — Woe to Those Who Clean the Outside but Are Filthy Within
“Woe to you, scribes and Pharisees, hypocrites! For you cleanse the outside of the cup and dish, but inside they are full of extortion and self-indulgence. Blind Pharisee, first cleanse the inside of the cup and dish, that the outside of them may be clean also.” (Matthew 23:25–26, NKJV)
Here, Jesus rebukes their obsession with external purity while inwardly harboring greed and excess. Outwardly, they followed ritual cleanliness, but inwardly they were morally filthy. The phrase “extortion and self-indulgence” denotes both exploitation of others and the unrestrained gratification of self.
They were blind to their inner condition, thinking that ceremonial washings were sufficient to make them holy. But Jesus says transformation must begin on the inside.
Psalm chapter 51 verse 6 says, “Behold, You desire truth in the inward parts, and in the hidden part You will make me to know wisdom.”
The righteousness that God demands is not mere appearance but a genuine cleansing from within. When the heart is made clean, the life will follow. True holiness is inside-out, not outside-in.
Matthew 23:16–22 – The Religious Leaders Made False and Deceptive Oaths
“Woe to you, blind guides, who say, ‘Whoever swears by the temple, it is nothing; but whoever swears by the gold of the temple, he is obliged to perform it.’ Fools and blind! For which is greater, the gold or the temple that sanctifies the gold? And, ‘Whoever swears by the altar, it is nothing; but whoever swears by the gift that is on it, he is obliged to perform it.’ Fools and blind! For which is greater, the gift or the altar that sanctifies the gift? Therefore he who swears by the altar, swears by it and by all things on it. He who swears by the temple, swears by it and by Him who dwells in it. And he who swears by heaven, swears by the throne of God and by Him who sits on it.” (Matthew 23:16–22, NKJV)
Jesus condemned the Pharisees for constructing a convoluted system of oaths, wherein some were binding and others were not, depending on the object sworn upon. Though they avoided invoking God’s name directly—perhaps out of respect for Exodus 20:7, “You shall not take the name of the LORD your God in vain”—they used deceitful distinctions to get around truth-telling. Jesus exposed their hypocrisy, revealing that every oath, even those they thought trivial, was made before God.
Jesus pointedly corrected their logic, asking, “For which is greater, the gold or the temple that sanctifies the gold?” This logic applies to the altar and the gift as well. The altar, as the divinely appointed place of atonement, sanctifies the offering placed upon it. It is a type of Christ, who is our true altar (Hebrews 13:10). He sanctifies not only the offering but also those who come to God by Him.
The altar’s features are spiritually significant:
Its purpose was to sanctify and sustain the offering, showing how Christ bears our judgment.
Its location was always at the forefront of the tabernacle or temple, revealing that no man approaches God without first going through the atoning sacrifice.
Its shape—a square, with horns on each corner—signifies completeness, strength, and divine justice and mercy.
Its material, bronze, speaks of judgment endured (cf. Numbers 21:9).
Its appearance, stained with blood, foreshadows the cross.
Its accessibility (no steps, per Exodus 20:26) shows that all, regardless of status, could approach.
Thus, swearing by the temple or altar still implicated God, because it involved His dwelling, His ordinance, and His throne. All oaths ultimately invoke divine accountability, even if cloaked in human schemes.
Matthew 23:23–24 – The Religious Leaders Were Obsessive about Trivialities but Neglected True Righteousness
“Woe to you, scribes and Pharisees, hypocrites! For you pay tithe of mint and anise and cummin, and have neglected the weightier matters of the law: justice and mercy and faith. These you ought to have done, without leaving the others undone. Blind guides, who strain out a gnat and swallow a camel!” (Matthew 23:23–24, NKJV)
The Pharisees’ zeal for tithing extended even to herbs—mint, anise, and cummin. Though technically commendable, it had become a façade. Their punctilious observance of minor tithes stood in stark contrast to their disregard for the “weightier matters of the law”: justice, mercy, and faith. These three virtues mirror Micah 6:8: “He has shown you, O man, what is good; and what does the LORD require of you but to do justly, to love mercy, and to walk humbly with your God?”
The gnat and the camel illustrate the absurdity. The gnat was the smallest unclean creature (Leviticus 11:23), while the camel was the largest unclean animal (Leviticus 11:4). The image is comical but cutting—religious leaders straining wine through cloth to avoid swallowing a gnat, yet spiritually gulping down a camel. They had lost all spiritual proportion.
Matthew 23:25–26 – The Religious Leaders Were Outwardly Clean but Inwardly Defiled
“Woe to you, scribes and Pharisees, hypocrites! For you cleanse the outside of the cup and dish, but inside they are full of extortion and self-indulgence. Blind Pharisee, first cleanse the inside of the cup and dish, that the outside of them may be clean also.” (Matthew 23:25–26, NKJV)
The Pharisees were satisfied with superficial righteousness. They meticulously followed ritual cleansings and made their lives appear pious, but inwardly, they were full of greed and indulgence. True spiritual cleanliness begins within. The internal must be transformed before the external can be pure. As Proverbs 4:23 says, “Keep your heart with all diligence, for out of it spring the issues of life.”
Matthew 23:27–28 – The Religious Leaders Were Like Whitewashed Tombs
“Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs which indeed appear beautiful outwardly, but inside are full of dead men’s bones and all uncleanness. Even so you also outwardly appear righteous to men, but inside you are full of hypocrisy and lawlessness.” (Matthew 23:27–28, NKJV)
Whitewashed tombs were common before Passover, marked to prevent Jews from becoming ceremonially defiled (Numbers 19:16). They were clean on the surface, but concealed death and corruption. Jesus accused the Pharisees of the same: externally impressive, but inwardly spiritually dead. Paul echoed this in Acts 23:3 when he called the high priest “a whitewashed wall.”
Matthew 23:29–36 – They Honored Dead Prophets but Murdered the Living
“Woe to you, scribes and Pharisees, hypocrites! Because you build the tombs of the prophets and adorn the monuments of the righteous, and say, ‘If we had lived in the days of our fathers, we would not have been partakers with them in the blood of the prophets.’ … Therefore, indeed, I send you prophets … some of them you will kill and crucify … that on you may come all the righteous blood shed on the earth …” (Matthew 23:29–36, NKJV)
These religious leaders pretended to venerate past prophets while plotting to kill the greatest of all—Jesus. They claimed they would not have joined in their fathers’ sins, but Jesus declared them sons of their fathers in guilt and conduct. He foretold their persecution of His followers (see Acts 7:52). He addressed them as “serpents, brood of vipers,” evoking John the Baptist’s earlier rebuke in Matthew 3:7 and Genesis 3’s imagery of Satan. They were of their father, the devil (John 8:44).
Jesus referenced “the blood of righteous Abel to the blood of Zechariah.” Abel was the first martyr (Genesis 4:8), and Zechariah was the last in the Jewish canon (2 Chronicles 24:20–22), covering the entire spectrum of prophetic martyrdom.
Matthew 23:37–39 – Jesus Laments Over Jerusalem
“O Jerusalem, Jerusalem, the one who kills the prophets and stones those who are sent to her! How often I wanted to gather your children … but you were not willing! … you shall see Me no more till you say, ‘Blessed is He who comes in the name of the LORD!’” (Matthew 23:37–39, NKJV)
Jesus wept for Jerusalem (Luke 19:41), the city that rejected the prophets and now Him. His desire was maternal and tender, to gather Israel like a hen gathers her chicks—providing protection, comfort, and identity. Psalm 91:4 says, “He shall cover you with His feathers, and under His wings you shall take refuge.” But they were not willing. They rejected His grace, and so their house—the temple—would be left desolate (fulfilled in A.D. 70).
The final verse hints at the Second Coming. Israel will one day repent and receive her King (cf. Zechariah 12:10; Romans 11:26). The phrase “Blessed is He who comes in the name of the LORD” (Psalm 118:26) will not be a casual greeting but a national recognition of the Messiah.
Woe #1 (Matthew 23:13):
“But woe to you, scribes and Pharisees, hypocrites! For you shut up the kingdom of heaven against men...”
This verse is foundational to the chapter's tone. Jesus condemns the leaders for blocking access to salvation—neither entering themselves nor allowing others to go in. This woe introduces the theme of spiritual obstruction that defines the entire chapter. (You covered this in earlier notes, but ensure it's still tied into the structure of the full eight woes.)
Verse 14 Omission:
Some manuscripts include Matthew 23:14: “Woe to you, scribes and Pharisees, hypocrites! For you devour widows’ houses, and for a pretense make long prayers. Therefore you will receive greater condemnation.”
This verse is omitted in some modern translations due to manuscript evidence, but it appears in Mark 12:40 and Luke 20:47, and fits thematically. You may choose to insert it parenthetically with a textual note.
Structure of the Woes:
The woes are not merely condemnations but are patterned accusations paired with specific hypocrisy. You might outline the pattern this way:
Woes 1–2: Hindering others from entering the Kingdom (spiritual obstruction).
Woes 3–4: Misguided evangelism and foolish casuistry (spiritual confusion).
Woes 5–6: Obsessive externalism (ritual over righteousness).
Woes 7–8: Dead religiosity and inherited guilt (spiritual death and legacy of rebellion).
The Legalism of the Pharisees:
You’ve done well covering how the scribes and Pharisees twisted the law. A short expansion might include Galatians 3:24–25, which clarifies the law as a tutor pointing to Christ. The Pharisees reversed this purpose—making the law an end in itself.
“Your house is left to you desolate” (Matthew 23:38):
This statement is prophetic and marks the official judgment of the temple and Jewish leadership. This is the moment Jesus turns His back on the temple, leading directly into the Olivet Discourse (Matthew 24–25), which begins with the disciples pointing out the temple buildings. Connecting this lament to the next chapter’s prophetic teaching can help contextualize the gravity of verse 38.
Christ’s Final Public Teaching:
Matthew 23 is the last recorded public teaching of Jesus in the Gospel before His arrest and crucifixion. It is significant that His final address is one of judgment on hypocrisy—marking a transition from offering the Kingdom to Israel to preparing for the cross.
Typology and Thematic Echoes:
Jesus’ lament mirrors the language of the prophets (especially Jeremiah and Hosea) when they warned of judgment upon Jerusalem. It underscores that Jesus is acting as the ultimate Prophet, Priest, and King.
