History tells us that the destruction of Jerusalem actually happened just as Jesus knew it would.  And destruction is the right word here.  Jerusalem was totally and utterly destroyed.  The Jewish historian Josephus was apparently an eye witness to the fall of the city, and he has left us an account of it.   Jesus says about the destruction of the great temple of Jerusalem "they will not leave one stone upon another within you."  According to Josephus these words of Jesus regarding the temple literally came true.  The temple was completely and totally destroyed. The events leading up to the destruction of Jerusalem started around the year 66 when the Jews revolted against the Romans.  After a four year struggle, the Roman legions besieged Jerusalem and after a siege of four months, they destroyed the city in the year 70. 

We picture Jesus weeping bitter tears.  I can think of several reasons for this grief.  First of all Jesus knew that there would be terrific loss of life during the Jewish revolt.  Included among them would be friends of Jesus and people who had heard him preach and teach.  Also people who witnessed some of his miracles.  Jesus very much valued his friends and those who followed him.  And their cruel death would naturally cause him great sadness.  Then there was the destruction of the temple.  The great temple of Jerusalem was a very special place for the people of Israel.  It was the location for contacting the One True God and seeking his help and his protection.  It was thus very important to all the people of Israel.  Its total destruction was a terrible blow to them.  The Menorah and the sacred vessels were taken to Rome.  The temple treasury was looted.  And as Jesus says the destruction was so complete that not one stone was left upon another.  When Jesus foresees all of this it causes him great anguish and he weeps for the people and their loss.  There was also the matter of the Diaspora, or the scattering of the Jews.  After the destruction of Jerusalem the whole land of Israel was devastated, and not fit to live in.  Many of the people moved to other lands, some at terrific distances from Israel.  The people of Israel, who had survived other periods of exile earlier in their history and had always returned to their land after a few generations, were destined to be scattered around the earth for nearly 2,000 years before some of them returned to the land of their ancestors.  They also were to undergo much persecution from the people of the lands where they settled.  The knowledge of all of this suffering for his people had to be a cause of great sorrow to Jesus.  He himself was a Jew and he loved the people of his land.  But Jesus also knew that the people of Israel did not always obey God, and this had to cause him sorrow.  And so Jesus wept over Jerusalem.