Matthew 23:29–36 | THE CHURCH PREPARED: Part II | Pastor Tanks | 10-18-2026 | Reach City Church

Judgment is coming, but God is not the bad guy for it. God’s warnings are not idle threats, and the reality of judgment is meant to make people mind how they walk in the in between. Judgment is not an indictment against God’s love, because judgment follows the repeated rejection of God’s mercy, God’s messengers, and finally God’s Son.

Jesus calls the scribes and Pharisees hypocrites because they wear a mask. Hypocrisy is not struggling to obey while trying to follow Christ. Hypocrisy is being content to do what flesh wants while knowing how to look, talk, and act righteous around church people. The Pharisees claimed they would never have killed the prophets, yet they were actively plotting to kill the Messiah standing right in front of them.

Jesus says, “Fill up then the measure of the guilt of your fathers,” because their family tradition was rejection. Their fathers killed the servants God sent, and this generation was about to kill the Son. God’s judgment is therefore accumulated judgment, not quick judgment. God kept sending servant after servant, then sent His Son, not to condemn the world at His first coming but so the world might be saved through Him.

God’s long suffering proves that He is slow to wrath and quick to show mercy. God’s patience is not approval of sin, and His kindness is meant to lead people to repentance. Rejection turns mercy into stored-up wrath, because the person rejecting Christ is rejecting the only One who removes the judgment already resting on a sinful world.

Jesus still sends messengers even after He is crucified. God adds to His church people who had participated in killing His Son, showing that repentance remains open even to the worst rejectors. Christ sends witnesses first to Jerusalem, the city that killed Him, because God wants to gather people like a hen gathers her chicks under her wings.

Jesus grieves over Jerusalem even while pronouncing judgment against it. God takes no pleasure in the death of the wicked, yet His love must run next to His justice. The church therefore cannot celebrate when wicked people fall under judgment. The gospel must be preached with urgency, truth, mercy, and a full picture of both salvation and judgment.

Christ’s return will be judgment for those who reject Him and salvation for those who eagerly await Him. Eagerly awaiting does not mean lip service without fruit. True repentance keeps turning from what flesh used to love toward the Christ who first loved sinners. Judgment is certain, but God has been beyond patient. The gathered and the scattered, the saved and the judged, come down to what people do with Christ.

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Key Takeaways

• 1. Judgment follows rejected mercy, not cruelty. God does not rush to condemn people for one failure or one moment of rebellion. His judgment follows long suffering, repeated calls to repent, and the rejection of the Son sent to save. The hard truth is that rejecting Christ leaves a person in the judgment from which Christ came to rescue them. [19:25]
• 2. Masks cannot replace repentance. Hypocrisy is not imperfect obedience from someone trying to follow Jesus. Hypocrisy is the intentional decision to look holy in public while privately refusing Christ’s authority. Fruit does not purchase salvation, but fruit exposes whether repentance is real or whether the lips are only performing Christianity. [48:26]
• 3. God grieves when judgment must fall. Jesus laments over Jerusalem immediately after declaring its coming desolation. God’s justice is never a joyful excuse to celebrate somebody else’s ruin, because He desires to gather, forgive, and restore. Christians must carry that same sorrowful heart when speaking hard truth or witnessing the consequences of sin. [38:24]
• 4. The gospel is God’s compassion going outward. Christ sends witnesses because His heart is to gather people rather than leave them scattered in judgment. A watered-down gospel cannot create the conviction, repentance, and Spirit-empowered life that the full gospel produces. Mercy requires both urgency and honesty about sin, judgment, the cross, and salvation. [41:44]
• 5. Eager waiting produces visible fruit. Hope in Christ’s return does not permit people to keep living however they want. Those who eagerly await Him keep repenting, obeying when obedience costs, forgiving when flesh wants revenge, and pursuing holiness when nobody is watching. The question is not merely whether repentance happened once, but whether repentance remains the posture of life.
  
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Youtube Chapters

• [00:00] - Welcome
• [03:16] - Judgment Is Coming, Don’t Blame God
• [03:41] - Warnings That Are Not Idle Threats
• [06:59] - Judgment and Accountability
• [08:49] - Hypocrisy and the Religious Mask
• [11:00] - Rejecting Christ Brings Judgment
• [15:51] - The Son Sent to the Vineyard
• [17:15] - God Is Long Suffering
• [20:18] - Christ Came to Save the World
• [24:50] - Mercy for Those Who Killed Jesus
• [29:28] - Patience Is Meant to Lead to Repentance
• [34:08] - Judgment Grieves the Heart of God
• [38:24] - Jerusalem and the Hen’s Wings
• [41:44] - The Full Gospel Must Be Preached
• [47:26] - Eagerly Awaiting Christ’s Return
• [52:16] - Choose the Gathered or the Scattered

Bible Reading

Matthew 23:29-39
“Woe to you, scribes and Pharisees, hypocrites! For you build the tombs of the prophets and adorn the monuments of the righteous, and say, ‘If we had been living in the days of our fathers, we would not have been partners with them in shedding the blood of the prophets.’ So you testify against yourselves, that you are sons of those who murdered the prophets. Fill up, then, the measure of the guilt of your fathers. You serpents, you brood of vipers, how will you escape the sentence of hell? Therefore, behold, I am sending you prophets and wise men and scribes; some of them you will kill and crucify, and some of them you will scourge in your synagogues, and persecute from city to city, so that upon you may fall the guilt of all the righteous blood shed on earth, from the blood of righteous Abel to the blood of Zechariah, the son of Berechiah, whom you murdered between the temple and the altar. Truly I say to you, all these things will come upon this generation. Jerusalem, Jerusalem, who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together, the way a hen gathers her chicks under her wings, and you were unwilling. Behold, your house is being left to you desolate! For I say to you, from now on you will not see Me until you say, ‘Blessed is He who comes in the name of the Lord!” [02:28]

John 3:16-18
“For God so loved the world, that He gave His only begotten Son, that whoever believes in Him shall not perish, but have eternal life. For God did not send the Son into the world to judge the world, but that the world might be saved through Him. He who believes in Him is not judged; he who does not believe has been judged already, because he has not believed in the name of the only begotten Son of God.” [20:19]

Romans 2:4-6
“Or do you think lightly of the riches of His kindness and tolerance and patience, not knowing that the kindness of God leads you to repentance? But because of your stubbornness and unrepentant heart you are storing up wrath for yourself in the day of wrath and revelation of the righteous judgment of God, who will render to each person according to his deeds;” [30:29]

Observation questions

1. In Matthew 23:29–36, what did the scribes and Pharisees claim they would have done differently from their fathers, and what were they actually doing toward Jesus?
2. What words and images does Jesus use in Matthew 23:37–39 to show both Jerusalem’s rejection and His desire to gather them? [38:24]
3. According to John 3:16–18, what is the purpose of Jesus’ first coming, and what condition remains for the person who does not believe in Him? [20:19]
4. In Romans 2:4–6, what is God’s kindness meant to produce, and what does an unrepentant heart store up instead? [30:29]

Interpretation questions

1. Jesus calls the Pharisees hypocrites because they honored prophets publicly while rejecting God’s Son in front of them. How does this show the difference between struggling to obey Christ and using religious language to hide a settled refusal to obey Him? [09:01]
2. Why is God’s patience not the same as God approving of sin? How does Romans 2 help explain why delayed judgment should lead a person to repent rather than become comfortable in rebellion? [29:49]
3. Jesus pronounces judgment over Jerusalem and then laments over it. What does this reveal about the way God’s justice and God’s compassion belong together? [36:13]
4. John 3 says that Christ came to save, while Matthew 23 warns of judgment for rejecting Him. Why is it important for Christians to speak honestly about both salvation and judgment when sharing the gospel? [40:20]

Application questions

1. Is there an area where it is easy to look faithful around other Christians while privately resisting what Christ has clearly called you to do? What would honest repentance look like in that specific area this week? [10:22]
2. God’s kindness is meant to lead us to repentance. What are some specific ways God has been patient and kind toward you recently? How should that kindness change a current habit, attitude, or relationship? [30:12]
3. When you see someone face consequences for sin, what is your first inward response—sorrow, pride, indifference, or satisfaction? How can Jesus’ grief over Jerusalem reshape the way you talk about people who are far from God? [37:49]
4. Who in your family, workplace, neighborhood, or friend group may need to hear the gospel from you? What could it look like to approach them with both truth about sin and genuine compassion for their salvation? [40:03]
5. Eagerly awaiting Christ means continuing to turn from what the flesh loves toward Christ. Where is God calling you to keep turning—through confession, obedience, forgiveness, or holiness when nobody is watching? [50:49]
6. When you are tempted to blame God, other people, or your circumstances for the results of your sin, what would taking personal responsibility before God sound like? [52:16]