Matthew 23 Part 3
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Matthew 23: Part 3 - The Final Woes
Matthew 23: Part 3 - The Final Woes
Matthew 23:27–39 concludes Jesus's condemnation of the scribes and Pharisees. He continues to exposes the difference between outward appearance and inward reality. He then mourns over Jerusalem's rejection of God's messengers, and explains that there is a coming judgment and a future day when Israel will recognize Him as the Messiah.
Matthew 23:27–28 — The Woe of the Whitewashed Tombs
Matthew 23:27–28 — The Woe of the Whitewashed Tombs
Jesus gives a second metaphor, condemning the scribes and Pharisees for appearing holy on the outside while their hearts are full of hypocrisy.
Woe unto you, scribes and Pharisees, hypocrites! for ye are like unto whited sepulchres, which indeed appear beautiful outward, but are within full of dead men’s bones, and of all uncleanness.
Jesus rebukes the scribes and Pharisees because despite their appearance, they are spiritually dead and morally corrupt. A newly painted tomb looks clean on the outside but contains death within, and Jesus says the Pharisees are the same.
This is the sixth of the "woes" Jesus pronounces against the scribes and Pharisees. Remember the word "woe" expresses both judgment and sorrow. Jesus is correcting them, but at the same time he is grieving over their refusal to repent.
The phrase "whited sepulchres" (whitewashed tombs) would have been familiar to the people in the crowd. Before major feasts such as Passover, tombs were painted white with lime to make them highly visible. This prevented people from accidentally touching them and becoming ceremonially unclean according to Numbers 19:16.
And whosoever toucheth one that is slain with a sword in the open fields, or a dead body, or a bone of a man, or a grave, shall be unclean seven days.
The tombs appeared bright, clean, and even beautiful, but inside they still contained decaying bodies and "dead men's bones."
Do we remember what hypocrites originally referred to?
Hypocrisy — ὑπόκρισις (hypokrisis) — Strong's G5272
Meaning: Hypocrisy, pretense, acting under a mask, dissimulation.
"Dead men's bones" symbolizes more than physical death. Throughout the Bible, death represents separation from God because of sin (Ephesians 2:1).
And you hath he quickened, who were dead in trespasses and sins;
The Pharisees appeared spiritually alive but were inwardly dead. This is why we have been discussing spiritual seed, the seed planted in our heart. Let’s look at Romans 2 where Paul is speaking to Jews about Gentiles that becoming Christians, but the overall message of the chapter applies to any religious hypocrisy:
For he is not a Jew, which is one outwardly; neither is that circumcision, which is outward in the flesh:
But he is a Jew, which is one inwardly; and circumcision is that of the heart, in the spirit, and not in the letter; whose praise is not of men, but of God.
Paul’s point here in Romans is that what matters is the inward work of the Holy Spirit that transforms the heart. It doesn’t matter what family, denomination, tribe, ethnicity, etc. that we belong to. What matters is if we have Jesus or Satan in our heart. Are we following light, or walking darkness.
Even so ye also outwardly appear righteous unto men, but within ye are full of hypocrisy and iniquity.
Jesus here is just explaining the meaning of His illustration of the whitewashed tombs. The scribes and Pharisees looked great on outside, but they were that moldy glass we discussed last week on the inside.
Jesus says they "appear righteous unto men." The key word is "appear."
Appear — φαίνω (phainō) — Strong's G5316
Meaning: To shine, appear, become visible, make known, seem, or give the appearance of.
But Jesus, sees the heart and that it reveals who we really are (we keep going back to that spiritual seed planted in our heart right?), we see this in (John 2:24–25)
But Jesus did not commit himself unto them, because he knew all men, And needed not that any should testify of man: for he knew what was in man.
Jesus says they were full of "iniquity."
Iniquity — ἀνομία (anomia) — Strong's G458
Meaning: Lawlessness, violation of God's law, wickedness, contempt for God's commands.
The very men who claimed to be experts of God's Law were called lawless by the Messiah.
That’s because God measures righteousness by the condition of the heart.
Matthew 23:29–32 — The Woe of Honoring Dead Prophets While Rejecting the Living Messiah
Matthew 23:29–32 — The Woe of Honoring Dead Prophets While Rejecting the Living Messiah
Jesus talks about how the Pharisees claim to honor the prophets, but are preparing to murder the very Messiah those prophets foretold.
Woe unto you, scribes and Pharisees, hypocrites! because ye build the tombs of the prophets, and garnish the sepulchres of the righteous,
Jesus rebukes the scribes and Pharisees because they decorate thee tombs of the prophets, but they are rejecting the very Messiah whom those prophets wrote about.
This verse begins the seventh "woe" against the scribes and Pharisees.
Build — οἰκοδομέω (oikodomeō) — Strong's G3618
Meaning: To build, construct, rebuild, restore, or edify.
Here it refers to decorating or restoring the tombs of the prophets as memorials.
Prophets — προφήτης (prophētēs) — Strong's G4396
Meaning: A prophet; one who speaks forth God's message under divine inspiration.
So these prophets were given the message about the Messiah directly from God.
Garnish — κοσμέω (kosmeō) — Strong's G2885
Meaning: To adorn, decorate, arrange, beautify, or put in order.
They invested time and resources into restoring and honoring the burial places of Israel's prophets at the same time they are plotting to kill Jesus.
Throughout Israel's history, God's prophets were often rejected because they called the people to repentance. We see this explained in:
Nevertheless they were disobedient, and rebelled against thee, and cast thy law behind their backs, and slew thy prophets which testified against them to turn them to thee, and they wrought great provocations.
Prophets like Elijah, Jeremiah, Zechariah, and others were persecuted for proclaiming God's Word.
And say, If we had been in the days of our fathers, we would not have been partakers with them in the blood of the prophets.
The scribes and Pharisees claimed that if they had lived during the time of Israel's ancestors, they would never have helped kill God's prophets. But at the same time they are rejecting Christ, failing to see He is who the prophets were speaking of.
In Hebrews it even lays out that God sent his prophets, and that culminated in the coming of His Son, Jesus Christ (Hebrews 1:1–2).
God, who at sundry times and in divers manners spake in time past unto the fathers by the prophets, Hath in these last days spoken unto us by his Son, whom he hath appointed heir of all things, by whom also he made the worlds;
Within days, many of these religious leaders would conspire to arrest Jesus.
Blood of the prophets – Refers to the unjust killing of God's faithful messengers throughout Israel's history. "Blood" represents both their violent deaths and the guilt incurred by those responsible.
We have to remember it is possible to condemn the sins of the past while repeating them in the present. How often would we be quick to point out someone else’s sin, but turn a blind eye to our own.
Wherefore ye be witnesses unto yourselves, that ye are the children of them which killed the prophets.
By claiming they would have acted differently than their ancestors, the scribes and Pharisees actually testified against themselves. Their own words and actions condemned them. They claimed to honor the prophets, but were giving false testimony against Jesus and would demand for Him to be crucified. After His resurrection, they would continue their opposition by persecuting His apostles and the early church (Acts 4–8).
The phrase "children of them which killed the prophets" means more than simply being physical descendants. In the Bible, "children" often describes those who share another person's character or conduct.
Children — υἱός (huios) (plural: huioi) — Strong's G5207
Meaning: Son, descendant, offspring; often used figuratively for one who shares another's character or nature.
The Pharisees were following in the spiritual footsteps of those that came before.
Jesus is not condemning them for the sins of previous generations. Scripture consistently teaches that each person is accountable for his or her own sin (Ezekiel 18:20).
The soul that sinneth, it shall die. The son shall not bear the iniquity of the father, neither shall the father bear the iniquity of the son: the righteousness of the righteous shall be upon him, and the wickedness of the wicked shall be upon him
They were guilty because of their sinful spirit and their own choices. By plotting against Jesus, they were proving that they were heirs of those who had persecuted the prophets.
This verse reminds us that our actions reveal our true spiritual family. Jesus teaches in (John 8:39-44) that those who do the works of God show they belong to Him, while those who imitate evil belong to the devil.
True spiritual heritage is demonstrated by faith and obedience to Jesus Christ.
Fill ye up then the measure of your fathers.
Jesus tells the scribes and Pharisees to complete the sins of their ancestors. He’s not encouraging them to sin, but is saying that by rejecting and crucifying Him, they would bring to completion the long history of Israel's rebellion against God's messengers and fill up the full measure of their guilt.
The word "measure" refers to a quantity that can be filled to its limit, like a cup. Throughout Scripture, this imagery is used to describe God's patience with sin.
This shows us that God has patience for us, but He will reach a point where judgment becomes inevitable.
Matthew 23:33–36 — The Judgment Upon the Guilty Generation
Matthew 23:33–36 — The Judgment Upon the Guilty Generation
Jesus calls the leaders "serpents" and "a brood of vipers," warns of coming judgment, and foretells the persecution of His disciples.
Ye serpents, ye generation of vipers, how can ye escape the damnation of hell?
Jesus rebukes the scribes and Pharisees, calling them "serpents" and a "brood of vipers" because of their hardened hearts. They would not escape God's judgment, unless they came to repentance.
The image of a serpent immediately recalls the serpent in Genesis 3, who deceived Eve into sin. Throughout the Bible, the serpent becomes a symbol of deception and evil, and just generally opposing God. Even though the Pharisees presented themselves as spiritual guides, they were actually leading people away from God's truth.
The phrase "generation of vipers" (or "brood of vipers") emphasizes that they shared the nature and character of the serpent. They spread spiritual corruption through false teaching and hypocrisy. John the Baptist had used the same expression when he confronted these leaders earlier in (Matthew 3:7).
Now I want to go over a few things here. We normally would look a this verse and immediately think of the Pharisees being from a corrupted lineage that’s beyond hope, right? But I want us to look at what John the Baptist said:
But when he saw many of the Pharisees and Sadducees come to his baptism, he said unto them, O generation of vipers, who hath warned you to flee from the wrath to come?
Bring forth therefore fruits meet for repentance:
John is saying that they can change their ways. They can repent. And if they do, their life will show it. The phrase "fruits meet for repentance" uses the imagery of fruit growing from a healthy tree. Just as a tree naturally produces fruit according to its nature, genuine repentance naturally produces visible changes in a person's life. The Greek word translated "meet" means worthy of, fitting, or appropriate to. So live a life worthy of the gifts of repentance.
The word "repentance" comes from the Greek metanoia, meaning a change of mind that results in a change of direction. Biblical repentance is more than feeling guilty or sorry for sin. It involves turning away from sin and turning toward God.
And think not to say within yourselves, We have Abraham to our father: for I say unto you, that God is able of these stones to raise up children unto Abraham.
John the Baptist is saying, "Don't assume you're right with God just because you're descendants of Abraham. God is not obligated to save you because of your ancestry. He can create children of Abraham from these very stones if He chooses."
Many Jews of that time believed that being born into Abraham's family gave them a special standing before God. Some had come to rely on their physical heritage instead of a personal relationship with God.
So what’s the point here? The point is the same thing we’ve discussed time and time again. It’s about the spiritual seed that is planted in out heart. The inside matters so much more than the outside. You can come from a corrupt bloodline and still find salvation through the blood of Jesus, or you can come from a great, Christian family and walk right into a life filled with wickedness. In fact, Jesus’s own lineage had some pretty bad people in it.
Judah slept with his daughter in law, thinking she was prostitute (Genesis 38:15-26), but then he admits his sin and ends up offering himself as a substitute for Benjamin.
Jacob deceived Isaac to take Esau’s blessing (Genesis 27:18-29), but then he receives the name Israel, grows in his faith, and becomes the father of the twelve tribes
David committed adultery with Bathsheba and then arranged the death of her husband (2 Samuel 11:2-17), but he was a man after God’s own heart, wrote many Psalms and was the king line establishing the throne of the Messiah
Solomon married foreign wives and turned to worshipping idols (1 Kings 11:1-10), but he builds the first temple and was considered one of the wisest men to live, and so on and so forth.
Jesus’s family tree includes liars, sexually immoral people, murderers, idolaters, and foolish rulers. But that lineage still culminated in the perfect Messiah. This shows that everyone has a choice. Everyone can be saved through Jesus, and God can and will use anyone he chooses regardless of their family, profession, status, whatever. I mean think about the fact that Tim Tebow was a Florida Gator, and God still uses him to spread the gospel all the time.
The Pharisees are not a lost cause that couldn’t repent and find salvation. But their hearts, that spiritual seed that’s planted within, are still corrupt at this point.
Jesus then asks, "How can ye escape the damnation of hell?" Their religious status, ancestry, the honor they demanded of the people, none of it could save them from God's judgment. Unless they repented and believed in Jesus, they would face eternal damnation.
The word translated "hell" is the Greek word Gehenna (Geenna). Gehenna referred to the Valley of Hinnom, located south of Jerusalem. In Old Testament times, this valley became infamous because some Israelites practiced child sacrifice there to the pagan god Molech (2 Kings 23:10; Jeremiah 7:31). King Josiah later defiled the site to end those practices. Jesus used it repeatedly to describe the destination of those who reject God.
Wherefore, behold, I send unto you prophets, and wise men, and scribes: and some of them ye shall kill and crucify; and some of them shall ye scourge in your synagogues, and persecute them from city to city:
Jesus declares that He will continue to send God's messengers to Israel, but many of them will be rejected, beaten, and killed.
Notice Jesus says: "I send unto you..." He does not say, "God will send," but "I send." This is a declaration of His divine authority. In the Old Testament, it was God who sent the prophets (Jeremiah 7:25). Here, Jesus claims that same authority.
The three groups Jesus mentions:
Prophets – Those who spoke God's revealed message under the guidance of the Holy Spirit (e.g., Agabus in Acts 11:27–28).
Wise men – Spiritually mature teachers who applied God's truth with wisdom. This term emphasizes godly understanding rather than a formal office.
Scribes – Teachers and interpreters of God's Word. Unlike the unbelieving scribes of Jesus' day, these would be disciples trained for the kingdom (see Matthew 13:52).
Some "ye shall kill and crucify." Stephen was stoned (Acts 7), James was executed by Herod (Acts 12:2), and according to early church documents, many of the apostles suffered martyrdom. The mention of crucifixion points to the Roman method of execution that would be used against Jesus Himself and later some of the disciples.
Others would be "scourged in your synagogues." Scourging was a Jewish punishment involving lashes that were given in synagogue courts (Deuteronomy 25:1–3). Jesus had already warned the disciples this would happen (Matthew 10:17).
Finally, they would be "persecuted... from city to city." This accurately describes the spread of persecution throughout the Book of Acts. Believers were forced to flee Jerusalem (Acts 8:1–4), and Paul was chased from city to city during his missionary journeys (Acts 13–14).
Ironically, the persecution intended to stop the gospel actually helped spread it. As believers scattered, they carried the message of Christ into new regions, fulfilling Jesus' commission to take the gospel to the ends of the earth (Acts 8:4)
That upon you may come all the righteous blood shed upon the earth, from the blood of righteous Abel unto the blood of Zacharias son of Barachias, whom ye slew between the temple and the altar.
Jesus declares that the Pharisees would bear responsibility for the long history of rejecting God's messengers. From the first righteous man murdered in Scripture (Abel) to the last martyr recorded in the Hebrew Scriptures (Zechariah), they were following the same pattern by rejecting and crucifying the Messiah.
They were not being condemned because of their ancestry, but because they committed the same kinds of sins as their forefathers.
The phrase "all the righteous blood shed upon the earth" refers to the murders of God's servants throughout biblical history.
Jesus ends with "Zacharias son of Barachias." This has been the subject of much discussion among Bible scholars.
The most widely held view identifies him with Zechariah, who was murdered in the Temple court during the reign of King Joash (2 Chronicles 24:20–22).
The mention of "son of Barachias" has led to several explanations:
Some suggest that Barachias was another name for the father of Zechariah in 2 Chronicles.
Others believe the phrase may refer to a grandfather or another ancestor, since Jewish genealogies sometimes omitted generations.
Despite the uncertainty over the name of the father, the location given by Jesus—"between the temple and the altar"—lines up with 2 Chronicles 24:21, where Zechariah was stoned in the court of the house of the Lord.
And they conspired against him, and stoned him with stones at the commandment of the king in the court of the house of the Lord.
Jesus is not saying the scribes and Pharisees personally murdered Abel or Zechariah, but by calling for the crucifixion of Jesus they were committing the same sins.
Verily I say unto you, All these things shall come upon this generation.
Jesus is saying they would experience the consequences of these actions within their own lifetime.
The phrase "all these things" refers back to the judgments Jesus described through verses 29–35.
The expression "this generation" has been interpreted in several ways, but the most widely accepted understanding is that Jesus was referring to the people living at that time, especially the generation that rejected Him as Messiah. Throughout Matthew, Jesus consistently uses the phrase "this generation" to refer to the people alive at that time (Matthew 11:16; 12:41–42, 45; 16:4).
In A.D. 70, the Roman army under General Titus besieged Jerusalem, destroyed the Temple, and devastated the city. This event marked the end of the Second Temple period and started the fulfillment of Jesus' earlier warnings about the coming judgment upon Jerusalem (Matthew 22:7; 24:1–2; Luke 19:41–44; 21:20–24).
But this prophecy has an end time meaning as well. It will be repeated in the end times when Jerusalem falls again under the Antichrist (Ezekiel 38; Zechariah 14).
Historically: The destruction of Jerusalem in 70 AD was the first fulfillment.
Spiritually: The warning is still future in the sense that God’s judgment applies to all generations who continue to reject Him
Eschatologically: The verse’s fulfillment will also include the end-time desolation of Jerusalem, as prophesied in Scripture
In short: Matthew 23:36 is no longer future in the sense of the first historical fulfillment, but it remains a future warning for those who reject God’s truth, with it extending into the end times.
Matthew 23:37–39 — Jesus' Lament Over Jerusalem
Matthew 23:37–39 — Jesus' Lament Over Jerusalem
Jesus mourns over Jerusalem's rejecting Him. He compares His desire to protect His people to a hen gathering her chicks, predicts the desolation of the Temple, and points ahead to the day when Israel will acknowledge Him as the Messiah.
O Jerusalem, Jerusalem, thou that killest the prophets, and stonest them which are sent unto thee, how often would I have gathered thy children together, even as a hen gathereth her chickens under her wings, and ye would not!
Jesus mourns over Jerusalem (meaning the people) because they repeatedly rejected God's messengers and refused His truth. He wanted to save and bless them, but they chose to reject Him.
Notice that Jesus's tone changes dramatically. He goes from judging to grieving. He expresses sorrow over Jerusalem.
The repetition, "O Jerusalem, Jerusalem," is a Hebrew way of speaking about the nation, the people, not just the actual city.
Jesus then says, "How often would I have gathered thy children together." This shows His persistent desire throughout history to call His people back to Himself. The attempts to gather the people came through the prophets, through John the Baptist, through Jesus' own ministry, and would continue through the apostles after His resurrection.
A mother hen spreads her wings to shield her chicks from danger, even if it puts her in harms way.
This echoes several Old Testament passages where God is pictured as sheltering His people beneath His wings:
Keep me as the apple of the eye, Hide me under the shadow of thy wings,
As birds flying, so will the Lord of hosts defend Jerusalem; Defending also he will deliver it; And passing over he will preserve it.
The final words in verse 37, "and ye would not," are so sad. The people refused to allow God to shelter them. To protect them. To save them.
God desires us to come to Him, but He does not force us to.
Behold, your house is left unto you desolate.
Jesus is saying that because Israel has rejected the Messiah, they will experience judgment. The Temple, once the center of God's presence among His people, will be abandoned and left in ruin.
The word "Behold" calls attention to the seriousness of what Jesus is about to say.
The phrase "your house" has been understood in two closely related ways:
Jesus will leave the Temple shortly after this (Matthew 24:1), and He will predict its complete destruction. But the broader meaning includes the spiritual desolation that would come upon the nation, and further the entire world because it had rejected its King.
Notice that Jesus says "your house," not "My Father's house." Earlier, Jesus referred to the Temple as "my Father's house" (John 2:16). Because of Israel's rejection, He now calls it "your house." This shows God's presence and favor being withdrawn from the Temple.
The word "desolate" means abandoned, forsaken, laid waste, or left empty. Its more than physical destruction; it points to spiritual abandonment. A temple, synagogue, church, whatever you would call the building, without God's presence its useless.
Remember this had it’s historical context fulfilled in 70 AD. The Temple has never been rebuilt.
But this verse is not the end of the story.
For I say unto you, Ye shall not see me henceforth, till ye shall say, Blessed is he that cometh in the name of the Lord.
Jesus tells the people that they will no longer see Him until the day they acknowledge Him as the promised Messiah.
Jesus is looking beyond the immediate future to God's ultimate plan.
Within a few days, He would be arrested, crucified, buried, and then resurrected.
The word "till" is important because it implies that the separation is temporary, not permanent.
The words "Blessed is he that cometh in the name of the Lord" are quoted from Psalm 118:26,
Blessed be he that cometh in the name of the Lord: We have blessed you out of the house of the Lord
a psalm that was sung during the Jewish festivals. The crowds had already shouted these words during Jesus' entry into Jerusalem (Matthew 21:9). But the nation's leaders rejected Him, and the crowd quickly turned on Him. They followed man.
Jesus points to a future where these words will be spoken with genuine recognition of His identity as the Messiah. This to refer to Christ's Second Coming.
This verse is the bridge between Jesus' first coming and His return. God's covenant promises have not failed. The Messiah will return in victory, and will be recognized for who He truly is.
As John concludes the book of Revelation,:
He which testifieth these things saith, Surely I come quickly. Amen. Even so, come, Lord Jesus.
Devotional Thought: A Heart That Welcomes Jesus
The greatest tragedy in this chapter is not that the religious leaders lacked knowledge—they knew the Scriptures well. It wasn't that they lacked religion—they were among the most devoted people of their day. The tragedy was that they knew about God but they didn’t KNOW GOD. They honored the prophets, but rejected the Messiah. They looked righteous but refused the One who could cleanse their sins and actually make them righteous.
That danger still exists today.
It's possible to for us to study the Bible, to attend Church, to pray, to do all of the things we think we should; but still not allow His love and truth to take root in our hearts. To instead allow our heart, our mind, our lives, to be consumed with the ways of the world. The wickedness and sinful ways that Satan has planted.
So how do we avoid this? What can we ask ourselves?
Is my relationship with Jesus genuine and growing, or has it become routine?
When Jesus calls me, do I willingly come?
God is far more interested in the condition of our hearts than the image we present. He doesn't ask us to be perfect; He asks us to be honest.
He searches our hearts and loves us enough to correct us. He can guard us from hypocrisy and pride. Creating a clean heart, and renewing our spirit. Jesus still invites us to come under His care and protection. We just have to stop resisting. He will accept us as we are, and will mold us to become who we should be.
Matthew 23: Part 3 - The Final Woes
Matthew 23: Part 3 - The Final Woes
