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Lessons from Seven Woes (Matthew 23:1-39)

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Lessons from Seven Woes (Matthew 23:1-39)



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Lessons from Seven Woes

Matthew 23:1-39 (Pastor Heo)

(One of my (Aaron’s) favorite chapters~)

Seven Woes

23:1-7pp — Mk 12:38,39; Lk 20:45,46 23:37-39pp — Lk 13:34,35

1 Then Jesus said to the crowds and to his disciples: 2 “The teachers of the law and the Pharisees sit in Moses’ seat. 3 So you must obey them and do everything they tell you. But do not do what they do, for they do not practice what they preach.4 They tie up heavy loads and put them on men’s shoulders, but they themselves are not willing to lift a finger to move them. 

5 “Everything they do is done for men to see: They make their phylacteries wide and the tassels on their garments long; 6 they love the place of honor at banquets and the most important seats in the synagogues; 7 they love to be greeted in the marketplaces and to have men call them ‘Rabbi.’ 

8 “But you are not to be called ‘Rabbi,’ for you have only one Master and you are all brothers. 9 And do not call anyone on earth ‘father,’ for you have one Father, and he is in heaven. 10 Nor are you to be called ‘teacher,’ for you have one Teacher, the Christ. 11 The greatest among you will be your servant. 12 For whoever exalts himself will be humbled, and whoever humbles himself will be exalted. 

13 “Woe to you, teachers of the law and Pharisees, you hypocrites! You shut the kingdom of heaven in men’s faces. You yourselves do not enter, nor will you let those enter who are trying to. (14?)

15 “Woe to you, teachers of the law and Pharisees, you hypocrites! You travel over land and sea to win a single convert, and when he becomes one, you make him twice as much a son of hell as you are. 

16“Woe to you, blind guides! You say, ‘If anyone swears by the temple, it means nothing; but if anyone swears by the gold of the temple, he is bound by his oath.’ 17 You blind fools! Which is greater: the gold, or the temple that makes the gold sacred? 18 You also say, ‘If anyone swears by the altar, it means nothing; but if anyone swears by the gift on it, he is bound by his oath.’ 19 You blind men! Which is greater: the gift, or the altar that makes the gift sacred? 20 Therefore, he who swears by the altar swears by it and by everything on it. 21 And he who swears by the temple swears by it and by the one who dwells in it. 22 And he who swears by heaven swears by God’s throne and by the one who sits on it. 

23 “Woe to you, teachers of the law and Pharisees, you hypocrites! You give a tenth of your spices–mint, dill and cummin. But you have neglected the more important matters of the law–justice, mercy and faithfulness. You should have practiced the latter, without neglecting the former. 24 You blind guides! You strain out a gnat but swallow a camel. 

25 “Woe to you, teachers of the law and Pharisees, you hypocrites! You clean the outside of the cup and dish, but inside they are full of greed and self-indulgence. 26 Blind Pharisee! First clean the inside of the cup and dish, and then the outside also will be clean. 

27 “Woe to you, teachers of the law and Pharisees, you hypocrites! You are like whitewashed tombs, which look beautiful on the outside but on the inside are full of dead men’s bones and everything unclean. 28 In the same way, on the outside you appear to people as righteous but on the inside you are full of hypocrisy and wickedness. 

29 “Woe to you, teachers of the law and Pharisees, you hypocrites! You build tombs for the prophets and decorate the graves of the righteous. 30 And you say, ‘If we had lived in the days of our forefathers, we would not have taken part with them in shedding the blood of the prophets.’ 31 So you testify against yourselves that you are the descendants of those who murdered the prophets. 32 Fill up, then, the measure of the sin of your forefathers! 

33 “You snakes! You brood of vipers! How will you escape being condemned to hell? 34 Therefore I am sending you prophets and wise men and teachers. Some of them you will kill and crucify; others you will flog in your synagogues and pursue from town to town. 35 And so upon you will come all the righteous blood that has been shed on earth, from the blood of righteous Abel to the blood of Zechariah son of Berekiah, whom you murdered between the temple and the altar. 36 I tell you the truth, all this will come upon this generation. 

37 “O Jerusalem, Jerusalem, you who kill the prophets and stone those sent to you, how often I have longed to gather your children together, as a hen gathers her chicks under her wings, but you were not willing. 38 Look, your house is left to you desolate. 39 For I tell you, you will not see me again until you say, ‘Blessed is he who comes in the name of the Lord.’ “


This is a hard message to take and receive, but we must take and receive it. This is Jesus’ LAST public message – a VERY critical take-down of false religion that operated under the guise of truth.

These Pharisees are legal copiers and scribes of the Law.

They believed that God gave the Law to Moses, he passed it to Joshua, he passed it to the elders, they passed it to the Pharisees – so they believed they were sitting on the seat of Moses. But they were hypocrites because to teach one thing and do another is wrong.

  1. Must do’s and Must Not do’s – this is what they preached, but Jesus came to make our burdens light.
  2. They had a false concept of greatness – recognition, praise from men. They loved to be called “Rabbi” and “Master”.

Through this LONG chapter, we saw 7 Woes.

Woe = a warning of judgment but a feeling of regret as well, mixture of judgment, sorrow, painful love – because the listeners don’t repent.

Let’s look at these seven briefly. But let’s not look to condemn THEM, rather to test OURSELVES.

  • Romans – “Everything written in the past was written to teach us.”
  • 2 Timothy 4:12? “All Scripture is God-breathed and useful for teaching, rebuking, correcting, and training so that the man of God may be equipped for EVERY good work.”
  • “Examine yourselves to be 

What is the meaning of Christian? “Saint” = separated from sin to sacredness.

WOE ONE: v. 13

  • Blessed is the poor in spirit for theirs is the kingdom of heaven (Matthew 5)
  • Cursed are the proud in spirit for they keep themselves and others out of the KOH (opposite)

It’s bad enough to keep ourselves out, but WORSE to stand in the way of others trying to enter the KOH.

We have NOTHING to DO – except believe in Christ as Savior and Lord – to enter the KOH. There’s no other way.

“I am the Way, the Truth, and the Life.”

WOE TWO: v. 15

Traveling over sea and land reminds us of missionary work – BUT what’s wrong here? They traveled to win souls to their Legalism – NOT to the living God – to their Phariseeism – not to God.

Our mission is to win souls to CHRIST. NOT to win souls to MY church or denomination.

Imagine how tragic it is when people believe that they are going to heaven, when they are really going to hell. Double conviction when they are wrong only produces double condemnation.

All religions are just made by man – these cannot lead us to heaven. “Salvation is found in no one else – except Christ” (Acts 3?)

WOE THREE: v.16-22

Remember Jesus’ words in Matthew 5

  • Blessed are those who hunger and thirst for righteousness for they will be filled.
  • Cursed are those who hunger and thirst for greedy gain, for they will be empty. (Opposite)

They wanted gold and gifts – why? To make money. But, they didn’t want the temple and the altar – no concern for it – because they couldn’t turn them into their own private property. They confused the externals for the eternals.

Yes, even today, people can confuse majors with minors. “What is your major?” (Science, ed, computer, bio) – but in your LIFE – “What is your major?” (Jesus) If not, Jesus, then you are “majoring” in the “minors” – only Christ can make your whole life perfect (eternally).

WOE FOUR: v. 23

Matthew 5

  • Blessed are the merciful, for they will be shown mercy.
  • Cursed are the unmerciful (oppressors) for they will NOT be shown mercy.

Here, Jesus doesn’t condemn the practice of tithing, but he did condemn their ATTITUDE without justice, mercy, and faith.

Tithe is NOT tax. It is a sign of faith in God who gives us all that we have.

  • Leviticus 27: “A tithe belongs to the Lord.”
  • Malachi 3:8 “Not tithing is ROBBING God.”

What we must remember = we must offer sacrifices to God with our HEARTS – not reluctantly, but willingly, for God loves a cheerful giver. Tithe alone cannot stand in for no justice, no mercy, no love, no faith, etc.

God’s all about the heart.

WOE FIVE: v. 25

Matthew 5

  • Blessed are the pure in heart, for they will see God.
  • Cursed are the defiled/dirty inside, for they will NEVER see God.

Imagine dirty bowls – whatever we put into it becomes unclean as well. Humans can be deceived, but God cannot be deceived.

WOE SIX: v. 27

At that time, Jews were VERY careful not to touch dead things or dead bodies – it would make them unclean (ceremonially). So they painted the outside of tombs WHITE – especially at Passover lest somebody accidentally defiled.

This is a graphic depiction of hypocrisy – outside is white and beautiful, but inside is dead and decaying.

WOE SEVEN: v. 29

Yes, Jesus will be crucified and killed shortly after this.

Jesus charged the history of Israel as a history of murder – killing the men of God. The Jews martyred the men of God throughout history.

Abel + Zechariah = the two examples here.

  1. Abel = Genesis 4
  2. Zechariah = Chronicles 24 – son of a priest, touched by the Holy Spirit, warned the people against their plans – king Joash ordered him to be killed so they stoned him to death.

Why Jesus calls him the last martyr in the Old Testament?

  1. In our Bible, the last book is Malachi.
  2. But in that time, the last book in their Bible was 2 Chronicles.
  3. There were 24 books in their Bible at that time.
  4. This means “from the first (Abel) to the last (Zechariah) – the history of Israel is murder”

Yes, Jesus knows that he will be one of these martyred/murdered and his disciples will be among them as well.

Here is a tragedy. Imagine how tragic this is that the nation that God chose and loved have turned their hands against God. Imagine, the day of Reckoning is coming.

Every person, every individual must answer this question.


Yes, Jesus is coming soon.

But we cannot read this severe denunciation, this critical condemnation without wonder – marvel – at the patience, goodness, and love of our Father God.

We know that throughout history, no nation has been blessed like Israel, but no nation has sinned against the patience, mercy of God like Israel.

Yes, they’ve been a GREAT channel of God’s blessing to the world. And at the same time, they SUFFER greatly.

  • Jesus was also born a Jew. So, we must thank God for the Jews – they gave us the Bible, God sent his Son through them.
  • Yes, we are Gentiles – we must love not only other Gentiles, but also the Jews. Because Jesus today is stretching out for the lost – not only for the Jews, but also the Gentiles.

This is the heart of God who wants all human beings to be saved and come to a knowledge of the truth.

“Your attitude should be the same as that of Christ.”

May God bless us with this kind of attitude.

Let’s pray.

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