“As He drew near, He saw the city (Jerusalem) and wept over it.” (v.41)
Our text tells us as Jesus drew near to the city of Jerusalem "He wept.” Why? Because the people did not know the scriptures well enough to understand the reason for His first coming (v.41-44), and those who did (scribes, chief priests, and Pharisees) sought to kill Him out of fear and jealousy.
The prophet Zechariah had described the 1st coming of Jesus over 500 years before it occurred writing, "Rejoice greatly, O daughter of Zion! Shout, O daughter of Jerusalem! Behold your King is coming to you; He is just and having salvation, lowly and riding on a donkey, a colt, the foal of a donkey" (Zechariah 9:9).
Zechariah correctly referred to Jesus as, "having salvation." Therefore, when Jesus did enter Jerusalem riding on a donkey as prophesied the people cried, "Hosanna!" or, literally, "Save now!" (Matthew 21:9). Why? Because they were hoping Jesus had come to save them from the Roman government and establish His kingdom on earth immediately - not to die on the cross for the sins of the world. Therefore, when He was eventually killed the Jews denied His claim as the Messiah, and are still blindly looking for their deliver today.
They missed it (His first coming), and this is what moved Jesus to tears "because they did not know the time of their visitation” (v.44). I believe Jesus still weeps today when someone rejects His moment of visitation (salvation) to them. Why? Because His second coming will be much different, and when that happens, He will no longer be the one weeping.
The Truth: "But the day of the Lord will come as a thief in the night, in which the heavens will pass away with a great noise, and the elements will melt with fervent heat; both the earth and the works that are in it will be burned up." (2 Peter 3:10)