Matthew 23:32-36 — Fill up, then, the measure of your fathers’ guilt. Serpents, brood of vipers! How can you escape the condemnation of hell? Therefore, indeed, I send you prophets, 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, that on you may come all the righteous blood shed on the earth, from the blood of righteous Abel to the blood of Zechariah, son of Berechiah, whom you murdered between the temple and the altar. Assuredly, I say to you, all these things will come upon this generation.”
After Jesus declared the woes on the rulers of Israel—the chief priests, the Pharisees and the leaders; He prophesied the coming judgement on them. Jesus spoke this knowing the Old Testament,
2 Chronicles 36:14-17 — All the officers of the priests and the people likewise were exceedingly unfaithful, following all the abominations of the nations. And they polluted the house of the LORD that he had made holy in Jerusalem. The LORD, the God of their fathers, sent persistently to them by his messengers, because he had compassion on his people and on his dwelling place. But they kept mocking the messengers of God, despising his words and scoffing at his prophets, until the wrath of the LORD rose against his people, until there was no remedy.
What the rulers of Israel did was nothing new, and they had now rejected God’s salvation through His Son. They rejected the Messiah—the Son of God. And not only did they reject Him, but they subsequently rejected, persecuted, killed, and crucified those whom the risen Lord sent to them with the offer of mercy in the gospel.
Jesus included this in the iniquity He charged against them, and He said that thereby they would fill up the measure of their fathers.
Paul confirms the wickedness of the Jews in his letter to the Thessalonians,
1 Thessalonians 2:16 — by hindering us from speaking to the Gentiles that they might be saved-so as always to fill up the measure of their sins. But God’s wrath has come upon them at last!
1 Thessalonians 2:16 — forbidding us to speak to the Gentiles that they may be saved; to fill up their sins always: but the wrath is come upon them to the uttermost.
Jesus and Paul both declared the iniquities and sins of that generation of Jews to have gone beyond the evil deeds of their fathers; and that the “wrath” which was then about to be poured out upon them was to be “to the uttermost.”