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When:

In general, it was the changeover from the Roman Republic to the Roman Empire. The world was about to be thrown into chaos from the insane and despotic Emperors that would come after Augustus.

In particular, the rise of the Empire meant the beginning of the Diaspora, as Jewish Zealots fought against worshipping Emperors as gods. The destruction of the Second Temple by the armies of Titus (who later became Emperor; Vespasian his father was Emperor during the destruction of the Temple) was the event that spread Jews far and wide across the known world, in order to survive.

Jesus was born at a time to tell the Jewish people - His people - what they could expect in a few decades, and have them remember it and document his words.

The Roman Empire was a model for the future final world government, and when He warned about the oppression His people would suffer, He was issuing a prophetic warning to all who recognized who and what He was.

Where:

Bethlehem, which was not the “hometown” of Jesus. It just so happened that His family had to travel there to be taxed as dictated by Augustus. Jesus and His immediate family lived in Nazareth.

Bethlehem was the necessary birthplace to fulfill Old Testament prophecy.

Micah 5:2 (KJV)

But thou, Bethlehem Ephratah, though thou be little among the thousands of Judah, yet out of thee shall he come forth unto me that is to be ruler in Israel; whose goings forth have been from of old, from everlasting.