Seven Woes of the Pharisees, Pt. 2

Nov 19, 2023

Seven Woes of the Pharisees, Pt. 2

Passage: Matthew 23:16-28

Preacher: Jeff Crotts

Series: Matthew

Category: Sunday Morning


  1. Woe to the hypocrites (vv. 23-28)

[KEY] What characterizes “hypocrites.”

  • What to avoid and remove from our lives.
  • What characterizes Pharisees.



  1. Inverted priorities (vv. 23-24)

[KEY] Scribes, Pharisees nt/criticized for precision w/the Law;

  • Their interpretation and application of God’s Law.
    • @/the Law, “What they say, goes!”
    • Whether honoring the Law’s intent or not.


  • Offer “tithe” of spices from their land.


  • X emphasizes Pharisees’ adherence to Leviticus 27 (v. 23).

ESV  Leviticus 27:30 "Every tithe of the land, whether of the seed of the land or of the fruit of the trees, is the LORD's; it is holy to the LORD. (Lev 27:30 ESV)


  • Pharisees counting specific numbers of spices and herbs w/precision.
    • Corrupting the point of tithing (offering a tenth) on the crops.
    • Meant as 10th of produce from God’s people in God’s land.
    • Precision as a cover for self-righteousness!


  • Provision to share back to others as an offering to God.


  • Pharisees giving as a show of “godliness” at expense of meeting needs.


  • Neglecting weightier matters of the law.


  • Loving neighbor as yourself.
    • Showing “justice” (v. 23), meeting needs of those downcast.
    • Showing “mercy and faithfulness.”
      • Heart motivations filled w/compassion.
        • Religious charade covering hard hearts.
        • Provokes the LORD w/inversion of priorities.


Verse 24 illustrates this inversion w/humor.

  • X calls them “blind guides” point to devastating influence on others.


  • “Blind leading the blind.”
    • People follow their example.
    • Modeling religious playacting as godliness, when exact opposite.


  • To “strain out a gnat” (v. 24) - using cloth to pour wine through, insuring drink purified from smallest unclean organism.


“Whatever you do, do not drink a microscopic insect!”


  • BTW, while doing this, you’re “swallowing” the largest unclean animal, “a camel!”


  • You think you’re being cleanest,
  • While spiritually filthy.



  1. Reverse cleanliness (vv. 25-26)

[KEY] Hypocrisy is operating in reverse. How Pharisees operated.

  • Hypocrites work “outside in” vs. “inside out.”


  • Jesus uses “cup” to illustrate.

[Illus] Imagine being offered a cup you could pour your drink @/dinner. At first glance cup seemed fine, but w/further examination, notice that though the outside clean, inside it is filled with scum. Picture dried coffee grounds inside. Unappetizing, repulsive. Plate analogy, same.

Hypocrites’ hearts are repulsive to God, “full of greed and self-indulgence” (v. 25).

[App] People work very hard to look the part, to scrub hard at the areas of life, what   people see, while leaving the scum residue inside the heart, untouched.


Verse 26 is both severe rebuke and guidance.

  • Condemnation w/Exhortation.


  • “You blind Pharisees! First clean the inside of the cup and the plate, that the outside also may be clean” (v. 26).


  • [Question] “How are you supposed to deal with greed and self-indulgence?”


  • Not countering w/big smile or smooth talking.
    • w/heart examination, looking in the mirror.
    • Taking inventory of heart motivations.


  • Acknowledging the Lord’s accountability.

[Illus] I remember while an associate in Little Rock, Judy and I lived across the street from a family whose husband was the senior pastor of another church. We were friends with he and his wife (she called herself “the first lady” of their church). They had cute kids and were good neighbors. That said, one thing always stood out and that was the penchant for having nice stuff.

I’m all for having nice things but this family who lived our or modest street of neighbors would drive very expensive cars (BMW’s and Mercedees) that revolved through as if he was a collector. Of course, this was none of my business and for the most part I ignored their stuff until one day I kept noticing a variety of vans dropping off new stuff like furniture and appliances.

So, I casually asked what the occasion for this new décor was, to which they replied that for the most part, everything in their home was being rented. This left me with the impression that rather than earning what they owned because they were wealthy, they were more concerned to keep up the appearance of being wealthy, when really not. This kind of pretense works, outside in, rather than inside out and this will eventually catch up to a person’s heart. And will drain the vitality from it.   

  1. External facades (vv. 27-28)

[TRANS] Last illustration taking up @/hypocrites; what provokes X.

  • Hypocrites are “whitewashed tombs” (v. 27).


  • Context of OT Law, important reference.
    • Carelessly touching the dead or the grave, rendered unclean.
    • Temporarily Disfellowshipped (Under discipline).

ESV  Numbers 19:16 Whoever in the open field touches someone who was killed with a sword or who died naturally, or touches a human bone or a grave, shall be unclean seven days. (Num 19:16 ESV)


  • Israelites prevention plan was to “whitewash”
    • WW2 landmines marked after battles on battlefield.
    • People would clearly see tombs as if backlit.
    • Ornamented!

ESV  Luke 11:44 Woe to you! For you are like unmarked graves, and people walk over them without knowing it." (Luk 11:44 ESV)

[KEY] X’s not complimenting Pharisee’s practice.

  • Instead, X personifies Pharisees as “whitewashed tombs.”
    • Focus on what’s wrong on the inside.
    • No matter how good outside appears.


  • Outside, scrubbed clean, while inside, “full of dead people’s bones and all uncleanness” (v. 27).
    • Touch dead or grave, disfellowshipped for 7 days.
    • A basic quarantine.


  • Jesus’ analogy makes the seriousness of hypocrisy run deeper.
    • More than “No Community Groups for a Week!”
    • Exposes spiritual status.
      • Living by façade is deeper than ceremony.
      • Spiritual death leads to eternal death.

ESV  Ephesians 2:1 And you were dead in the trespasses and sins (Eph 2:1 ESV)

ESV  James 1:13-15 Let no one say when he is tempted, "I am being tempted by God," for God cannot be tempted with evil, and he himself tempts no one. 14 But each person is tempted when he is lured and enticed by his own desire.

15 Then desire when it has conceived gives birth to sin, and sin when it is fully grown brings forth death. (Jam 1:13-15 ESV)


  • Hypocrites are self-entombed!
    • Trapped inside their crypt, mausoleum.
    • Constant contact w/own “dead people’s bones” (v. 27).


  • Self-contaminant.
    • Vicious cycle of self-perpetuating death.
    • Tomb-like existence in need of rescue.

Verse 28 summary: “outwardly [you] appear righteous to others but within you are full of hypocrisy and lawlessness” (v. 28).

  • Façade fools people, but not an all-seeing God.
    • He knows when people’s hearts.
    • He sees games while running recklessly.  



Bible tells a story filled with characters marked by hypocrisy.


  • Adam and Eve
  • Cain
  • Pharoah’s Magicians
  • Every Idol (Golden calf, Ex. 3).
  • False prophets

Judas Iscariot (Gospels)

  • False seed
  • The tares
  • Ananias and Saphirra  
  • So-called brother (1 Cor. 5)
  • False Apostles (2 Cor.)


  • Diotrephes
  • False teachers
  • False spirits


  • 1/3 of the angles
  • Anti-Christ/Mystery Babylon
  • Hell (Matt. 7, “depart from me I never knew you”)


Why is Jesus so provoked by this sin?  


  • They appear godly.
  • They garner trust.
  • They make disciples.
  • They build a work-based façade.
  • They make people dead.


How to fight and kill this sin.

  • Godliness comes through to your heart.
  • Focus from the inside out contra to outside in.  
  • Build trust with others by providence and faithfulness.  
  • Make disciples of the Gospel, of Christ.  
  • Live a grace-driven life defined by Scripture.
  • Pray the Spirit makes people alive by conversion.  

Modern masks to be warned of.

  • Intellectual.
  • Financial security.
  • Self-confidence.
  • “Good” friends.
  • Spirituality.  
  • Justice-driven.
  • Ecumenical.
  • Egalitarian.

Hypocrisy is subtle and the worst mask of being “religious”.

Make a trade. Someone lost in hypocrisy, trade mask of religion for a true relationship w/X.


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