Jesus quotes Deuteronomy and Leviticus to summarise the Law, confounds the religious leaders with a question about whose son the messiah might be, then insults the Pharisees and religious leaders again: Mark 12:28–34; Matthew 22:34–40; Mark 12:35–37; Matthew 22:41–46; Luke 20:41–44; Mark 12:38–40; Matthew 23:1–12; Luke 20:45–47; Matthew 23:13–39; Mark 12:41–44; Luke 21:1–4
After a string of strong accusations of hypocrisy against the Pharisees, Jesus turned His attention to Jerusalem:
Matthew 23:37-39 O Jerusalem, Jerusalem, the city that kills the prophets and stones God’s messengers! How often I have wanted to gather your children together as a hen protects her chicks beneath her wings, but you wouldn’t let me. And now, look, your house is abandoned and desolate. For I tell you this, you will never see me again until you say, ‘Blessings on the one who comes in the name of the Lord!’
Was Jerusalem, and her house, abandoned and desolate? The answer is yes. As Jesus spoke, it was a done deal. Jerusalem was abandoned by God for rejecting His Son, and the natural consequences, the 70AD destruction of Jerusalem, would be certain to follow.
But what about the claim Jerusalem would never see Jesus again? Most commentators interpret this as a sign of the second coming: when the Jews accept Jess as the Messiah, and mourn the one they have pierced, then Jesus will return.
You could get picky and point out that Jerusalem did see Him again: when they crucified Him, when He was resurrected, and when He ascended. But there were no crowds hailing Him as the Messiah (contrast this to His entry into Jerusalem only a day or two earlier). The resurrection itself was witnessed by only a few, the first were women and then He visited the disciples, and many saw Him in the next 40 days. But again, no crowds welcoming their Messiah.
The message here is that Jerusalem and her inhabitants had their chance to welcome their Messiah. In not taking it up, Jerusalem would be destroyed, and the Messiah they missed the first time around would come back only when they realised what they had done.