Matthew Chapter 23

Matthew 23 — “They Preach but Do Not Practice: The Judgment of Hypocrisy and the Heart of True Authority”

Matthew 22 exposed false wisdom and hardened unbelief.
Matthew 23 now exposes false holiness.

After answering their traps,
Christ turns from debate to judgment.

This chapter teaches one central truth:

The Kingdom is destroyed by hypocrisy and built by humility, truth, and lived obedience.

1. Moses’ Seat

“Then Jesus said to the crowds and to His disciples, ‘The scribes and the Pharisees sit on Moses’ seat.’” (Matt 23:1–2)

Christ acknowledges their office.
They teach the Law of God.

St John Chrysostom writes:

“He honors the seat, but condemns the life; the authority, not the hypocrisy.”
(Homilies on Matthew)

Truth may be preached by unworthy mouths.
The Word remains holy even when the messenger is not.

2. “Do What They Say, Not What They Do”

“For they preach, but do not practice.” (v. 3)

This is the definition of hypocrisy:
truth on the lips, falsehood in the life.

St Augustine explains:

“They sit in Moses’ seat but do not walk in Moses’ way.”
(Sermons)

Doctrine without conversion
becomes condemnation.

3. Heavy Burdens

“They bind heavy burdens, hard to bear, and lay them on men’s shoulders.” (v. 4)

They multiply rules
without mercy.

St Gregory the Great teaches:

“They demand what they will not carry, and command what they will not fulfill.”
(Pastoral Rule)

Authority without compassion
becomes tyranny.

4. Love of Display

“They do all their deeds to be seen by men.” (v. 5)

Religion becomes theater.

St Jerome writes:

“They sought applause on earth, not reward in heaven.”
(Commentary on Matthew)

External holiness
hides internal emptiness.

5. Desire for Titles

“They love the place of honor… and to be called Rabbi.” (vv. 6–7)

They crave recognition.

St Ambrose comments:

“He who seeks honor has already lost virtue.”
(On the Duties of the Clergy)

Spiritual pride
is more dangerous than open sin.

6. One Teacher, One Father

“You are not to be called rabbi… for you have one Teacher.” (vv. 8–10)

Christ forbids rivalry,
not instruction.

St Hilary of Poitiers explains:

“He forbids pride, not ministry; for all authority must serve truth.”
(On Matthew)

All teaching in the Church
flows from Christ.

7. The Law of Greatness

“He who is greatest among you shall be your servant.” (v. 11)

This repeats Matthew 20.

St Augustine writes:

“To be great is to be small for God.”
(Sermons)

The Kingdom reverses
human ambition.

8. First Woe: Shutting the Kingdom

“You shut the kingdom of heaven against men.” (v. 13)

They block salvation
by false example.

St Jerome says:

“They neither enter themselves nor allow others to enter.”
(Commentary on Matthew)

False guides
kill souls.

9. Second Woe: Corrupt Conversion

“You make him twice as much a son of hell as yourselves.” (v. 15)

They convert to party,
not to God.

St John Chrysostom observes:

“They multiply disciples, not saints.”
(Homilies on Matthew)

Zeal without truth
breeds corruption.

10. Third Woe: Blind Oaths

“Blind guides… whoever swears by the gold of the temple…” (vv. 16–17)

They twist morality
for profit.

St Gregory the Great writes:

“They weigh words but ignore hearts.”
(Homilies)

Legalism replaces conscience.

11. Fourth Woe: Tithing Without Justice

“You tithe mint and dill and cumin, and have neglected the weightier matters of the law.” (v. 23)

They measure herbs
and ignore mercy.

St Augustine teaches:

“They keep small commandments and trample great ones.”
(Sermons)

Ritual without charity
is empty.

12. Straining Gnats, Swallowing Camels

(v. 24)

Petty precision
with moral blindness.

St Jerome comments:

“They avoid tiny faults and commit enormous sins.”
(Commentary on Matthew)

13. Fifth Woe: Clean Cups, Dirty Hearts

“You clean the outside of the cup… but inside they are full of greed.” (v. 25)

Appearance replaces reality.

St Ambrose writes:

“God looks not at the vessel, but at what fills it.”
(On Repentance)

Holiness must begin
within.

14. Whitewashed Tombs

(vv. 27–28)

Beautiful outside,
dead inside.

St Gregory the Great says:

“They shine before men and rot before God.”
(Homilies)

This is the climax
of hypocrisy.

15. Sixth Woe: Tombs of the Prophets

“You build the tombs of the prophets…” (v. 29)

They honor dead prophets
while killing the living one.

St John Chrysostom remarks:

“They praise the past and persecute the present.”
(Homilies)

Tradition without obedience
becomes mockery.

16. Filling the Measure

(v. 32)

History reaches its crisis.

St Augustine explains:

“The patience of God ends when repentance is refused.”
(Sermons)

Judgment matures
with rejection.

17. “Serpents, Brood of Vipers”

(v. 33)

Not insult,
but diagnosis.

St Gregory the Great teaches:

“He calls them vipers because their malice kills truth.”
(Homilies)

Strong words
serve salvation.

18. The Sending of Prophets

“I send you prophets, wise men, and scribes…” (v. 34)

Grace persists
even in judgment.

St Ambrose writes:

“He threatens punishment and still offers mercy.”
(On Repentance)

Rejection is chosen,
not imposed.

19. The Blood of the Righteous

(v. 35)

From Abel to Zechariah,
history testifies.

St Jerome says:

“All righteous blood cries for justice.”
(Commentary on Matthew)

Christ gathers
all persecution into Himself.

20. “O Jerusalem, Jerusalem”

“How often would I have gathered your children…” (v. 37)

This is the cry of divine love rejected.

St Augustine writes:

“He wept in words before He wept in flesh.”
(Sermons)

Judgment comes
through sorrow.

21. “Your House Is Left Desolate”

(v. 38)

The Temple is abandoned.

St Gregory the Great explains:

“When God departs, emptiness remains.”
(Homilies)

Desolation
follows refusal.

22. The Future Hope

“You will not see Me again, until you say, ‘Blessed is He who comes in the name of the Lord.’” (v. 39)

Even judgment ends in promise.

St Ambrose writes:

“He closes with hope, that repentance may still return.”
(On Luke)

Israel’s story
is not finished.

Christ in Matthew 23

Jesus is:

• the True Teacher
• the Judge of Hypocrisy
• the Defender of the Simple
• the Voice of the Prophets
• the Rejected Messiah
• the Mourner for Jerusalem
• the Truth Incarnate

Spiritual Application

Fear hypocrisy more than sin.

Live what you teach.

Choose mercy over display.

Seek humility, not titles.

Cleanse the heart first.

Listen to living truth.

Do not kill the prophets of your time.

Let Christ gather you.

Closing Prayer

Lord Jesus Christ,
true Teacher and righteous Judge,
You exposed false holiness
and wept over the city that rejected You.

Deliver us from hypocrisy of heart and tongue.
Teach us to live the truth we confess,
to love what You command,
and to serve rather than to be seen.

Cleanse us within,
gather us under Your mercy,
and keep us faithful to Your word,
until the day when every false mask falls
and Your truth alone remains
in the Kingdom of heaven.

Amen.