Luke 19:41

‘And when he drew near, he saw the city and wept over it,'

Then Jesus moved solemnly on towards the city, and as He saw its future He wept over it. His thoughts were full and overflowing. He had no pleasure at the thought of the judgment that was coming on this city because of what they were going to do to Him. There was only the thought of, ‘Father forgive them, for they know not what they do'. There is something hugely dramatic about this entry into Jerusalem, with Jesus offering Himself as its King and Messiah, and yet weeping because He knows that it will reject Him and bring on itself its own judgment, even though the final result will be God's offer of salvation to the world.

For a comparison with the weeping of Jeremiah over what was to happen to the old Jerusalem see Jeremiah 8:18; Jeremiah 8:21; Jeremiah 9:1; Jeremiah 15:5. He too foresaw hope following disaster (Jeremiah 29:10; Jeremiah 31:31).