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  • Writer's picturePastor Brett

Woe to Jerusalem

Matthew 23:37-39 (cf Luke 13:34-25)

We are here in Matthew 23 one more time for two reasons of which I am aware. One, these words of Jesus complete His pronouncement of the seven woes which we spent the first five Sundays in Lent studying. Two, these words appear in a different place in Luke’s Gospel. There, Jesus speaks them during the Triumphal Entry, just before entering the city.

These are words of woe and warning. They also give us insight into Jesus’ heart, which was broken over some people’s refusal to see the truth. There is also a measure of frustration as He resigned them to the outcome they chose.

I imagine Jesus felt like the old Jewish man who had gone to the Western Wall in Jerusalem every day for many years. He had gone there every day for 70 years to pray for peace between Jews, Muslims, and Christians. He told anyone who would listen that he prayed for an end to hatred and wars. He prayed daily for the safety of everyone’s children, that they might grow up and love one another. He prayed that politicians in all countries would tell the truth and put the interests of all people ahead of their careers.

Someone asked him, “How do you feel after doing this for 70 years?”

“Like I’m talking to a wall,” the old man said.

Surely this is how Jesus felt as He gave this final public statement. He must have felt the walls of their stubbornness, frustrated by their unwillingness to receive the truth. Here at the end Jesus made it clear they had sowed the seeds of their own destruction.

Woe to Jerusalem, the city that welcomed Jesus as King, then crucified Him as a criminal.

1. The sins that led to the woes.

The first of these sins was their persecution of the very people God had sent to help them = “YOU KILL THE PROPHETS AND STONE THOSE SENT TO YOU.” (37) This repeats Jesus’ accusation against them in vs. 29-32, (last week’s message). By rejecting God’s messengers, they rejected God. Jesus’ complete condemnation of the religious leaders was for the public’s benefit: to show they could expect no help from that lot. Look at verse one to see to whom Jesus said all these words. It was not to the hypocrites themselves. It is as if Jesus said to them, “I’ve tried to reach you. I see now there is no hope, and I must go around these hypocrites to save the people.” As we saw in vs. 30-32, Jesus was the latest in a line of men who were SENT to the Jews with messages from God, only to suffer rejection, persecution, and even murder at their hands.

The second sin was their resistance to God’s invitation to be saved; “YOU WERE NOT WILLING” to be gathered to God. (37) They actively resisted God, substituting their own righteousness for the righteousness of God. Ezekiel 18:32 affirms God’s will for all human beings: “For I take no pleasure in the death of anyone,” declares the Sovereign LORD. Repent and live!”

2. Jesus came to love them.

“I HAVE LONGED TO GATHER YOUR CHILDREN TOGETHER,” Jesus said. (37) Jesus desired to do the thing the Messiah was supposed to do; unite the people of God under His rule.

In Ruth 2:12, Boaz’s blessed Naomi and Ruth: “May you be richly rewarded by the LORD, the God of Israel, under whose wings you have come to take refuge.” This metaphor of a momma bird is a common biblical image of God’s protection of His people; I would estimate 70 or more such references. This means Jesus’ declaration, “AS A HEN GATHERS HER CHICKS UNDER HER WINGS,” (37) is a touching and appropriate image for God’s love for His people. It is a picture of God’s tender love and the great security He offers the faithful.

3. The outcome of the city’s sins.

Sadly, Jesus declared, “LOOK, YOUR HOUSE IS LEFT TO YOU DESOLATE.” (38) Does the word HOUSE refer to the temple, the city, the nation, or the dynasty of David? It could be all the above. Their shared future is not a bright one. The word DESOLATE could be translated as “abandoned.” When we remember that Jesus is called “Emmanuel (God with Us),” His immanent death will certainly result in loss of fellowship with God. He would feel God the Father’s absence on the cross (Matthew 27:45-46).

Jesus also warned them, “YOU WILL NOT SEE ME AGAIN UNTIL YOU SAY, ‘BLESSED IS HE WHO COMES IN THE NAME OF THE LORD.’” (39) The opportunity was now lost to them; Jesus’ Triumphal Entry was their last chance to receive Him as their Messiah. From then on, everything that happened would be directed toward the cross. Ironically, “BLESSED IS HE WHO COMES IN THE NAME OF THE LORD” is one of the things the crowds accompanying Jesus into Jerusalem had already said to him (Matthew 21:9; Luke 19:34-35). It is a quotation of Psalm 118:26. However, it was mostly the pilgrims coming into the city for Passover that said that. The residents of the city were the ones who called for His crucifixion.

The fulfillment of Jesus’ words did not occur after His resurrection, for He did not appear to any unbelievers, but only to the brothers (1 Corinthians 15:6-8). This prophecy will be fulfilled at Jesus’ Second Coming. He will then appear to all people and all will proclaim Him as Lord. The faithful will say it out of reverence, the faithless out of terror, realizing too late they were wrong.

After saying these words, Jesus walked out of the temple (24:1), never to return to it again. Historically, the city of Jerusalem was destroyed by the Roman Emperor Titus in 70 A.D.

Woe to Jerusalem, the city that welcomed Jesus as King, then crucified Him as a criminal.

Let us avoid the error of ignoring the voice of God, turning aside from His call to repent, and be saved. We would rather blame others than acknowledge our sin.

We are like the man who was concerned his wife was losing her hearing. A friend counseled him to perform a harmless test. He told the man to stand about 40 feet away from her, ask her a question in a normal, conversational tone and volume. If he got no response, he was to get 10 feet closer and ask again, repeating this until he got a response.

He got home that evening and found his wife cooking supper. From the doorway he asked, “Honey, what’s for dinner?” He received no answer.

He stepped inside and a little closer to her. He asked again, “Honey, what’s for dinner?” Again, he got no reply.

Taking his friend’s advice, he got closer still and repeated the question. Yet again, he received no answer.

Trying one more time and now near her elbow but still behind her, he said, “Say, what’s for dinner?” She turned on him suddenly and said, “FOR THE FIFTH TIME, WE’RE HAVING CHICKEN!!”

May this Holy Week be the time in your life you are at your most attentive to the voice of God. Jesus has so much to say to you and it begins with this: “Watch and see how much I love you.”


Zondervan Bible Commentary, Matthew, H.L. Ellison

Interpretation, Matthew, Douglas R.A. Hare

The Expositor’s Bible Commentary, Vol. 8, Matthew, D.A. Carson

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