Why did Jesus break out in tears?

The road from Bethany, where Jesus had raised Lazarus from the dead, to Jerusalem takes you over the Mount of Olives. As Jesus passed the summit he would have seen the entire city in all its ancient grandeur. His reaction is recorded in the gospel of Luke; "When I saw the city spread out before me, I broke into teas" (19:41). As the OT prophets often wept over Israel's sin and impending judgment, so did Jesus as he looked ahead in just a few years to the destruction of Jerusalem. In A.D. 70 the Romans under the general Titus in a three-year siege would utterly destroyed the city and all its inhabitants. However it was more than just the physical destruction of the city that brought Jesus such pain.  The fall of Jerusalem represented the “failure” of God to fulfill a loving plan for those he had created. Luke writes, "If you had only recognized at this time what makes for peace!"
       What I would like to emphasize is Jesus' sensitivity to the tragic events that lay ahead. His reaction upon viewing the beloved capital of God's people and realizing its soon destruction, did not bring some gentle tears of sadness, but as the text says, he "broke into tears" — a strong word in the Greek text, used, for example, to describe Peter who, after denying Jesus, “went outside and wept bitterly” (Luke 22:62). Once again I want to stress the absolute oneness that Jesus shares with us. He is not a God that watches us from a distance like so many of the ancient gods. He was there on the road down to the beloved city and his sorrow over what would happen to that sacred place moved him so deeply that he broke out crying. His tears in no way revealed some sort of emotional weakness; they were the normal reaction of a strong man deeply moved about what would soon happen to his city.
       Let’s transfer Jesus’ reaction to the coming destruction of our contemporary “Jerusalem” How would he – in fact, how does he – react to the devastation that will fall upon this earth when he comes again to take us home? I know that the necessary anthropomorphisms involved in speaking of God fails to transfer fully to us what actually happens, but it does give us a sense of what God must feel. There are so many things that must grieve our Lord, such as the tragedies of sickness and death, the inhumanity of war, as well as what we might consider to be less evil – pride, distaste, and greed.
       My question is whether we as his children share the same abhorrence to sin? I would not call for a morose and negative attitude toward the wickedness that goes on in our world, but I believe it would be like Christ to be so positive about what is good that the flipside of life would be seen as genuinely evil. We see that balance in the life of Christ and sincere believers who are walking close by their Lord.

"Help us Lord to look out on our Jerusalem, love it for what it represents, sorrow for what has become, and be filled with joy for what it can be when it accepts the good news of your love."