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Matthew 23:1-39 - Woes, Hypocrisy, and the Lament over Jerusalem

23 min read

After the hostile questions in the temple, Jesus turns to the crowds and to His disciples. He does not open with a slogan against authority. He opens with a seat. The scribes and Pharisees sit in Moses’ seat. Israel still has a public place of teaching, and the people are told to observe what is truly taught. Then one sentence names the wound of the whole chapter: they say, and do not do.

That split is why the woes cut so deeply. Souls are being shut out of the kingdom by teachers who love to be seen. Yet the chapter will end with a hen gathering her chicks. The same Lord who cries “Woe” is the Lord who says, “How often I wanted to gather your children together.” The Church therefore hears this first as a word about her own mouth, her own burdens, her own hunger for honor, and her own resistance to being gathered.

Moses’ Seat and the Humble Servant (Matthew 23:1-12)

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. 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. 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.

Jesus speaks to the multitudes and to His disciples together. The warning is public, and it is also formation for those who will later teach in His name. The scribes and Pharisees sit in Moses’ seat: they occupy the visible place of instructing Israel in the Law. The people are not released from God’s word because some teachers have failed. “Whatever they tell you to observe, that observe and do.” Then the nerve of hypocrisy is cut: “do not do according to their works; for they say, and do not do.”

True words can sit on the tongue while the life remains proud, heavy, and unconverted. 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. A parent can demand a holiness he will not practice in the house. A priest or servant can impose a rule he will not help anyone carry. A teacher can love the sound of rigor more than the person crushed under it. The issue is not God’s commandment. The issue is leadership that displays weight and withholds a hand.

All their works they do to be seen by men. Phylacteries and garment borders are named here, yet the fault the Lord assigns is the hunger for display. Broad reminders of Scripture, enlarged borders, the best places at feasts, the best seats in the synagogues, greetings in the marketplaces, and the doubled title “Rabbi, Rabbi” become symptoms of a deeper appetite: to be honored as master. The practices themselves must not be turned into a caricature of Jewish life. Christ condemns works arranged around reputation.

Then He turns to His own: 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 in heaven. Do not be called teachers, for One is your Teacher, the Christ. Christ is not abolishing Orthodox spiritual fatherhood or pastoral order; He is striking at ambition and the possessive claim to master souls. Scripture itself knows fathers, teachers, and the care of souls. Every Christian father and teacher remains derivative. God is the true Father. Christ is the true Teacher. The brethren stand under Him.

The remedy is greatness as service. “He who is greatest among you shall be your servant.” The exalted will be humbled, and the humbled will be exalted. Authority in the kingdom is purified when the teacher bears what he teaches, takes the lower place, and refuses to use a holy name as a private throne.

Language insight: heavy burdens

The Greek behind “heavy burdens” names loads that are grievous to carry (phortia barea). Paired with the leaders’ refusal to move them with a finger, the wording identifies merciless, non-participating leadership rather than condemning discipline itself. Counsel is Christian when it helps a person bear Christ’s yoke. It becomes hypocrisy when it only displays the teacher’s strength.

Gems from the Fathers 💎: Truth Received, Pride Refused

St John Chrysostom reads this opening as a careful balance. Christ preserves reverence for Moses’ seat while forbidding imitation of corrupt works. The people are to hold to the Law even when those who teach it have become depraved in life. Chrysostom then turns the warning toward Christian rulers: the good leader is stricter with himself and gentler toward those he guides. That is the opposite of the pattern Christ condemns: heavy burdens for others, honors for oneself.1

Woes Against Blocking the Kingdom (Matthew 23:13-24)

“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. 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. “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. “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. “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!

The repeated “woe” is prophetic grief joined to judgment. The first tragedy is shutting up the kingdom of heaven against men. They neither go in themselves nor allow those who are entering to go in. The guide who should open the way becomes the obstacle. This still happens whenever religious leadership makes repentance harder, mercy smaller, or God seem less accessible than He is. A servant can do it with contempt. A parish can do it with a door that looks holy and feels closed.

The next woe is more concrete still. They devour widows’ houses, and for a pretense make long prayers. Therefore they will receive greater condemnation. The approved NKJV source includes Matthew 23:14; this study makes no textual-critical claim about the verse. The moral claim of the wording is already sharp. To devour widows’ houses under long prayers is to use ministry, money, and religious cover to take from people who cannot easily refuse. It can look like spiritual counsel that binds a lonely woman to a servant’s control. It can look like pressure around offerings, fees, favors, or “blessings” extracted from the poor. It can look like a prayer spoken over someone whose house, savings, or labor is being quietly consumed. Long prayers cannot make that holy.

St John Chrysostom hears the cruelty of taking from the poor while appearing pious. Those who should have relieved a widow’s need instead made her poorer, and the long prayer became a cloak for the theft. Mercy for the vulnerable is not decoration around worship. It is one of the tests by which Christ measures the prayer itself.2

Zeal can reproduce the same illness. They travel land and sea to win one proselyte, and when he is won they make him twice as much a son of hell as themselves. Evangelism, catechesis, and recruitment are not automatically holy. A convert can be trained into our pride, our faction, our contempt, and our hunger for control. If we form people in our likeness rather than in Christ’s, we have traveled far in order to shut the kingdom more efficiently.

The casuistry about oaths exposes a similar blindness. They say that swearing by the temple is nothing, while swearing by the gold obliges. Swearing by the altar is nothing; swearing by the gift obliges. Christ asks which is greater: the gold, or the temple that sanctifies the gold; the gift, or the altar that sanctifies the gift. The outward religious object has been treated as more binding than the holy reality that gives it meaning. 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. He who swears by heaven swears by the throne of God and by Him who sits on it. Distinctions that protect convenience while emptying reverence are a form of blindness.

Then comes the tithe of mint and anise and cummin. Christ does not despise faithfulness in small things. “These you ought to have done, without leaving the others undone.” The neglected matters are named: justice and mercy and faith. A person can be exact with herbs and swallow a camel of injustice. Small obedience used to avoid the weightier things is not piety. It is a screen.

Language insight: the weightier matters

The comparative behind “the weightier matters of the law” (ta barytera tou nomou) gives Christ’s ordering, not a dismissal of tithing. Justice, mercy, and faith must govern the small observances rather than be evaded by them. Care in herbs is not the enemy. Care in herbs as a substitute for mercy is.

Gems from the Fathers 💎: Prayer That Cannot Cloak Exploitation

Chrysostom’s reading of the widow-woe keeps the condemnation from floating into vague moralism. Prayer that accompanies the devouring of a poor person’s house is not merely imperfect devotion. It is pretense, and it brings greater condemnation. The Church must therefore look at money, power, and the people least able to refuse, especially where religious language is thickest.2

The Inside of the Cup and the Blood of the Prophets (Matthew 23:25-36)

“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. “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. “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 you are witnesses against yourselves that you are sons of those who murdered the prophets. Fill up, then, the measure of your fathers’ guilt. Serpents, brood of vipers! How can you escape the condemnation of hell? Therefore, indeed, I send you prophets, 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, that on you may come all the righteous blood shed on the earth, from the blood of righteous Abel to the blood of Zechariah, son of Berechiah, whom you murdered between the temple and the altar. Assuredly, I say to you, all these things will come upon this generation.

The next woes go inside. The cup and dish are clean outside but full of extortion and self-indulgence within. Whitewashed tombs appear beautiful outwardly and are full of dead men’s bones and all uncleanness. The point is not that outward conduct is worthless. Jesus says, “first cleanse the inside of the cup and dish, that the outside of them may be clean also.” Inner repentance and outward righteousness belong together, and the order matters. The heart must be healed. Appearance cannot be managed as a substitute for conversion.

This is a necessary warning for Orthodox Christians because our tradition is richly visible: liturgy, vestments, fasting, hymnody, prostrations, titles, and parish honor. These are holy when they express repentance and worship. They become dangerous when they cover extortion, self-indulgence, pride, or lawlessness. Christ does not set fasting, worship, or ascetic observance against inner conversion; He commands a cleansing of the inside that makes the outside clean also. The call is not to a thinner religion. It is to a whole life, where the inside and the outside both belong to God.

The last woe in this section exposes another hypocrisy: honoring the prophets after they are dead while refusing their living call. Building tombs and adorning monuments can look like reverence. The speakers even congratulate themselves: if they had lived in the days of their fathers, they would not have shared in the prophets’ blood. Christ says they are witnesses against themselves. A Church can praise saints, quote Fathers, keep beautiful memorials, and still silence the repentance those saints preached.

The woes belong first to the Church’s own hypocrisy, and they give no warrant for collective ethnic blame or for attributing this judgment to later Jewish generations. Jesus, His mother, His apostles, the prophets, and the first believers are Jewish. Christ speaks here to a specific generation and leadership in a temple conflict. “Assuredly, I say to you, all these things will come upon this generation.” The Church receives that word as a mirror: Do we honor the dead righteous while resisting living correction? Do we love the monuments of holiness while protecting the sins holiness would expose?

From Abel to Zechariah the Lord gathers the canonical sweep of righteous blood. The text itself supplies that range. The historical identification of Zechariah son of Berechiah is not settled by the evidence used here, and the debate should not become the lesson. What the passage does say is enough: resistance to God’s messengers has a long memory, and the rejection now gathering around Christ will reveal its heart. “Serpents, brood of vipers! How can you escape the condemnation of hell?” The warning is not to be softened. It is also not to be taught as cold denunciation. The next sentences will show the Judge’s desire.

Jerusalem, Jerusalem (Matthew 23:37-39)

“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 together, as a hen gathers her chicks under her wings, but you were not willing! See! Your house is left to you desolate; for I say to you, you shall see Me no more till you say, ‘Blessed is He who comes in the name of the Lord!’ ”

The chapter does not end with a sneer. It ends with a name spoken twice: “O Jerusalem, Jerusalem.” The repetition is personal and grieving. The same Lord who has announced woe now says, “How often I wanted to gather your children together, as a hen gathers her chicks under her wings, but you were not willing!” The condemnation of hell and the desolation of the house must be taught from Christ’s lament: He wanted to gather, and the warning is severe because His desire was real.

The hen image is tender and protective. Christ desired to cover, shelter, and save. The tragedy is named as unwillingness. God is not indifferent. The human will can refuse the gathering mercy of God. Repentance begins when the scattered heart stops defending its independence and lets itself be gathered.

“See! Your house is left to you desolate.” Religious structures without repentance cannot save. The temple, the city, and the visible house cannot protect a people who refuse the One to whom all worship points. Matthew 24 will take up that desolation as Jesus leaves the temple. Even here the last word is not only ruin. “You shall see Me no more till you say, ‘Blessed is He who comes in the name of the Lord!’” Those words are the acclamation of Psalm 118:26 (LXX Ps 117:26). The rejected One remains the Coming One. The future confession is already placed on the Church’s lips.

Language insight: I wanted, you were not willing

The Greek juxtaposition of gathering together (episynaxai) and “you were not willing” (ouk ethelesate) is the pastoral center of the lament. It should not be inflated into a complete theory of grace and freedom. It does rule out teaching the woes as divine indifference. The Lord wanted to gather. The wound is refusal.

Gems from the Fathers 💎: The Hen’s Wings and Christ’s Desire

St John Chrysostom hears pity in the repeated “Jerusalem” and in the hen gathering her brood. The image discloses warmth of love and the protection of wings, not a detached anger. The woes are severe because the love is real. The Church must teach the whole chapter from that heart: Christ exposes hypocrisy because it harms souls, and because He still desires to gather those who resist Him.3

The Church’s Voice in Worship ⛪

In the Coptic lectionary, Matthew 23:1-39 is the Matins Gospel on the Sunday of the sixth week of Great Lent. The Church therefore hears Christ’s exposure of hypocrisy within the season of repentance: the aim is compunction and return to the One who wants to gather us, not superiority over others. Matthew 23:14-39 is the Liturgy Gospel on Saturday of the fifth week of Great Lent; its concentration on the woes and the lament deepens Lenten self-examination. No named saint, feast, or received wider-Orthodox title is verified for this passage placement. No named commemoration is established by this evidence. Recurrent fixed-day Liturgy subranges of Matthew 23 exist in the Coptic cycle. Date-specific feast or Synaxarium associations require verification. Those subranges should not be taught as the meaning of this session.

The Lenten hearing keeps the passage from despair. The One who rebukes hypocrisy is walking toward the Cross. He exposes the wound in order to heal it. The right response is not contempt for ancient Pharisees. It is the prayer of the sixth week: Lord, cleanse the inside of the cup. Lord, make my service humble. Lord, gather what is scattered in me.

Spiritual Fruit 🍇

The fruit of Matthew 23 is humble integrity under the Christ who wants to gather us.

  1. Confess the split between speech and life. The simplest hypocrisy is still the deadliest: they say, and do not do. Before teaching a child, a class, or a parish, ask whether the word has first judged your own mouth, temper, money, and hidden habits. Bring the contradiction to confession rather than managing the appearance.

  2. Carry what you bind. If you lead a home, a ministry, or a friendship in Christ, do not lay a burden you refuse to touch. Sit with the person who is struggling. Share the fast you recommend. Help bear the repentance you name. Greatness in this chapter looks like a servant’s hand under someone else’s shoulder.

  3. Starve the hunger to be seen. Best seats, greetings, and titles still recruit the heart. Let every fatherly or teaching name remain transparent to the one Father and the one Teacher. If honor has become necessary to you, take a lower place on purpose: arrive early to serve, refuse the story that makes you central, and bless the person who is unnoticed.

  4. Give justice, mercy, and faith their proper weight. Keep the small obediences, and stop using them as a screen. If your fasting is careful while your speech is cruel, if your ritual is exact while a widow, a worker, or a quiet parishioner is being used, Christ has already named the camel. Restore what you have taken. Practice mercy where it will cost you. Believe God enough to do the weightier thing.

  5. Let yourself be gathered. Extortion, self-indulgence, whitewashed appearance, and the honoring of dead saints while resisting living correction all scatter the soul. The Lord still wants to gather His children. Stop defending the unwillingness. Pray the lament until it becomes consent: gather me under Your wings.

Stand in the temple after the questions have failed, and hear the Lord speaking to the crowds and to the disciples. The seat of Moses is still occupied. Burdens are still being bound. Widows can still be consumed under the cover of prayer. Cups still shine while the inside stays uncleansed. Then hear the voice change: “O Jerusalem, Jerusalem.” The Judge is the hen who wanted her chicks. Do not leave the house desolate by refusing Him. Say the coming confession now: Blessed is He who comes in the name of the Lord.

Footnotes

  1. St John Chrysostom, Homily LXXII on Matthew, on Matthew 23:1-12, especially Moses’ seat, receiving true teaching, and humility in leadership, https://www.ccel.org/ccel/schaff/npnf110.iii.LXIX.html ↩

  2. St John Chrysostom, Homily LXXIII on Matthew, on Matthew 23:14 and the exploitation of widows under a cloak of prayer, https://www.ccel.org/ccel/schaff/npnf110.iii.LXX.html ↩ ↩2

  3. St John Chrysostom, Homily LXXIV on Matthew, on Matthew 23:37-39 and Christ’s grieving desire to gather Jerusalem, https://www.ccel.org/ccel/schaff/npnf110.iii.LXXI.html ↩

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