"And David went up by the ascent of Mount Olivet, and wept as he went up, and had his head covered, and he went barefoot: and all the people that was with him covered every man his head, and they went up, weeping as they went up" (II Samuel 15:30).
The Mount of Olives overlooks Jerusalem from the east. This first reference to it notes the sad occasion when King David had to flee Jerusalem for his life, escaping the conspiracy of his estranged son Absalom.
Just as David wept over Jerusalem as he left it, so would his greater son, Jesus, a thousand years later, weep over the city as He entered it from Mount Olivet (Luke 19:37,41). It was there that He gave the great prophecy of His second coming (Matthew 24:3). It was also there He went with His disciples after the last supper, and there He agonized in prayer, alone, in the Garden of Gethsemane (Mark 14:26,32). Finally, after His death and resurrection, it was from the Mount of Olives that He ascended back into heaven (Acts 1:10-12).
This is far from the end of the story, however. The Mount of Olives has an amazing role yet to play in the world's future, according to a prophecy given long ago. "Behold, the day of the Lord cometh, . . . And His feet shall stand in that day upon the Mount of Olives, which is before Jerusalem on the east, and the Mount of Olives shall cleave in the midst thereof toward the east and toward the west, and there shall be a very great valley; and half of the mountain shall remove toward the north, and half of it toward the south" (Zechariah 14:1,4). Instead of a mountain there will be a valley, and "living waters shall go out from Jerusalem" (v.8). Instead of a mountain for weeping there will be a stream of rejoicing, and "the Lord shall be king over all the earth" (v.9). HMM