When Jesus stood in the temple and pronounced a series of woes upon the religious rulers of Israel—the scribes, Pharisees, and temple leaders—He was not merely rebuking their behaviour.

He was prophetically announcing the coming judgment that would soon fall upon that very generation. These were not empty threats. They were covenantal warnings with historical roots and eternal consequences.

Filling Up the Measure of Their Fathers #

Jesus spoke these piercing words:

Matthew 23:32–36 (AMP) — “Fill up, then, the [allotted] measure of the guilt of your fathers [to the brim so that nothing may be wanting to a full measure]. You serpents, you spawn of vipers, how can you escape the penalty of hell? Therefore take notice, I am sending you prophets and wise men and scribes (instructed interpreters of the Scriptures); some of them you will kill and even crucify, and some you will flog in your synagogues and pursue and persecute from city to city, so that on you may come [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. I assure you and most solemnly say to you, all these things [the divine judgment] will come on this generation.”

The expression “fill up… the measure” comes from the Greek word plēroō (πληρόω), meaning “to complete, bring to fullness.” This was Jesus’s way of declaring that the present generation had reached the full quota of rebellion, hypocrisy, and murderous hostility toward God’s messengers. In other words, the sins of their fathers were now brought to completion through them.

Jesus’s words were not in isolation. He was echoing a long history of Israel’s rejection of God’s prophets—a history that climaxed in the rejection of the Son Himself.

The Old Testament Record of Rebellion #

This consistent rebellion is summarised with pain and clarity in the book of Chronicles:

2 Chronicles 36:14–17 (AMP) — “All the officials of the priests and the people were very unfaithful [following] all the repulsive acts of the pagan nations; and they defiled the house of the Lord which He had sanctified in Jerusalem. The Lord, the God of their fathers, sent word to them again and again by His messengers, because He had compassion on His people and on His dwelling place. But they kept mocking the messengers of God and despising His words and scoffing at His prophets, until the wrath of the Lord arose against His people, until there was no remedy or healing.”

The phrase “no remedy” comes from the Hebrew marpē (מַרְפֵּא), meaning “healing” or “cure.” Israel had so repeatedly resisted the warnings of God that they had moved beyond the reach of prophetic correction. Now, history was repeating itself—but with even greater severity.

They had rejected the Son of God, and they would go on to reject the ones He would send—the apostles, prophets, teachers, and evangelists—those commissioned with the message of the New Covenant.

Killing Those Sent with the Gospel #

Jesus not only accused them of killing the prophets of old, but He prophesied that they would also kill and crucify those He was about to send. These were New Covenant messengers—apostles and disciples who carried the message of salvation in Christ.

The use of “crucify” here is significant. Crucifixion was not a Jewish mode of execution—it was Roman. Yet Jesus declared they would use even Gentile systems to destroy His messengers.

This happened repeatedly in the Book of Acts and early church history. Stephen was stoned. James was killed with a sword. Paul was beaten, imprisoned, and eventually executed. Wherever the gospel went, persecution followed, from the hands of both Jews and Gentiles.

Paul Repeats the Charge #

Paul, writing to the Thessalonian church, confirmed that the Jewish leaders continued the same pattern of hostility against the gospel:

1 Thessalonians 2:16 (AMP) — “Forbidding us from speaking to the Gentiles so that they may be saved; so as always to fill up [to the brim] the measure of their sins. But God’s wrath has come upon them at last [completely and forever].”

The phrase “fill up the measure” is again anaplēroō (ἀναπληρόω) in Greek, meaning “to fill up completely or to make full again.” It’s the same idea Jesus used—they were completing a cycle of rebellion and resistance that began with their ancestors.

Paul also uses the phrase “the wrath has come upon them.” The Greek here is orgē (ὀργή), meaning “settled indignation, divine anger.” This was not an emotional reaction but the righteous judgment of God upon a covenant-breaking people.

This Generation: The Object of Judgment #

Jesus made it plain that the coming judgment would fall upon “this generation”—not a future generation, but the one alive during His earthly ministry.

This is a covenantal phrase that often appears in Scripture. In Greek, “generation” is genea (γενεά), meaning “a group of contemporaries, people living at the same time.” Jesus was referring to that historical group of people who had rejected their Messiah and would seal their rebellion by persecuting the apostles.

The culmination of that judgment came in AD 70 when Jerusalem was destroyed by the Romans. The temple was burned, over one million Jews perished, and the Old Covenant system came to a final, visible end. Jesus’ prophecy was fulfilled in staggering detail.

All Righteous Blood #

Jesus mentioned the blood of Abel (the first martyr in Genesis) to Zechariah (a prophet murdered at the temple). This spans the entire Hebrew Scriptures—from Genesis to 2 Chronicles in the Hebrew canon order. It’s Jesus’s way of saying: “From the first righteous man to the last, you have followed the same pattern.”

The charge was not merely individual, but corporate. They stood in the lineage of those who killed God’s messengers, and they were now finishing what their fathers had begun.

What Does This Teach Us Today? #

The lesson is not only historical—it’s deeply spiritual. It reminds us that religion without repentance leads to judgment. That God’s patience is not eternal, and there comes a point where the measure of sin is filled. When the covenant is rejected and mercy is despised, only wrath remains.

It also teaches us that Jesus was not a victim of circumstance. He knew the cross awaited Him. He knew rejection and persecution were coming for His disciples. And yet, He continued forward in obedience and love, knowing that His sacrifice would open the way for a new covenant founded not on law, but on grace.

In Christ,
Shaliach.