• On that day •
What day is this most wonder filled day? It is the day of the testimony of the Two Witnesses in Jerusalem — when Jerusalem’s blindness is removed and she looks toward heaven for Yehoshua and says, “Blessed is he who comes in the name of Adonai!”
Zechariah continues:
9 And on that day I will seek to destroy all the nations that come against Jerusalem. 10 And I will pour out on the house of David and the inhabitants of Jerusalem a spirit of compassion and supplication, so that, when they look on him whom they have pierced, they shall mourn for him, as one mourns for an only child, and weep bitterly over him, as one weeps over a first-born.
For, concerning that day the prophecy says at the opening of the chapter:
Lo, I am about to make Jerusalem a cup of reeling to all the peoples round about; it will be against Judah also in the siege against Jerusalem. 3 On that day I will make Jerusalem a heavy stone for all the peoples; all who lift it shall grievously hurt themselves. And all the nations of the earth will come together against it.
• the Lord will put a shield about the inhabitants of Jerusalem •
Although Jerusalem did not put her arms around Yehoshua to embrace him, he puts his arms around her to shield her from the enemy — from all the nations when they gather together against her.
• so that the feeblest among them on that day shall be like David •
As David was strong through faith, so all Jews in that day shall be strong through faith in their Mashiach and the knowledge of his holy sacrifice.
• and the house of David shall be like God, like the angel of the Lord, at their head •
The house of David... This is the King in that generation. This term is used in order to make references to the hope of the house of David in every generation. This is Mashiach. He shall be compared to God. He shall be like the angel of Adonai who went before the camp of Israel. This is the Shekinah Glory, the Holy Divine Presence. For then Mashiach shall go before the children of Jerusalem and the People of Israel like a pillar of fire and smoke. And he shall lead them into the full possession of the promise of God.
Hidden Messiah "...you will receive power when the Holy Spirit comes on you; and you will be my witnesses in Jerusalem, and in all Judea and Samaria, and to the ends of the earth.” After he said this, he was taken up before their very eyes, and a cloud hid him from their sight. Acts 1:8-9