"What happened on the Mount of Olives?"
In the Old Testament, the Mount of Olives is mentioned once in relation to King David. When David's son Absalom wrested control of Jerusalem, David and his loyal followers fled the city via an eastern route: "David continued up the Mount of Olives, weeping as he went; his head was covered and he was barefoot. All the people with him covered their heads too and were weeping as they went up" (2 Samuel 15:30). Later, King Solomon used the Mount of Olives for idol worship: "On a hill east of Jerusalem, Solomon built a high place for Chemosh the detestable god of Moab, and for Molek the detestable god of the Ammonites" (1 Kings 11:7). In one of Ezekiel's visions, the prophet sees the glory of the Lord depart from Jerusalem and come to rest "above the mountain east of it" (Ezekiel 11:23).
Jesus made many visits to the Mount of Olives (Luke 21:37). In fact, it was "usual" for Him to go there when in the vicinity of Jerusalem (Luke 22:39). Every time Jesus visited Lazarus and Mary and Martha, He was on the Mount of Olives, for their village of Bethany was situated on the eastern slope. The road from Bethany to Jerusalem lay over Olivet.
The Bible records Jesus' visiting the Mount of Olives three times in the last week of His earthly life, and each time something of significance happened. The first visit was to deliver what has come to be known as the Olivet Discourse, recorded in Matthew 24:1—25:46. Parallel passages are found in Mark 13:1–37 and Luke 21:5–36. The content of the Olivet Discourse is Jesus' response to His disciples' question "When will these things be, and what will be the sign of your coming and of the close of the age?" (Matthew 24:3). Jesus' teaching in Matthew 24—25 primarily concerns the future tribulation period and the second coming of Christ at the end of the tribulation. The Discourse includes parables about those who wait for the Master's coming—the wise and faithful servant (Matthew 24:45–51), the five wise virgins (Matthew 25:1–13), and the good servant who uses his resources wisely (Matthew 25:14–30).
Jesus' second visit is what we call the triumphal entry. The donkey Jesus rode that day was found in the area of Bethany and Bethphage, on the east side of the Mount of Olives (Luke 19:29–30). Then, "when he came near the place where the road goes down the Mount of Olives, the whole crowd of disciples began joyfully to praise God in loud voices for all the miracles they had seen" (verse 37). While still on the Mount of Olives, Jesus looked at the vista in front of Him, wept over the city, and pronounced a judgment against it (verses 41–44).
Jesus' third visit during the week of His passion was on the night He was betrayed. That evening began with the Last Supper in Jerusalem and ended in the Garden of Gethsemane on the Mount of Olives. During that last Passover meal, Jesus washed His disciples' feet and then revealed Judas as the betrayer (John 13:1–30). At the conclusion of the meal, Jesus established the New Covenant and instituted the Lord's Supper (Matthew 26:26–29; 1 Corinthians 11:23–26). Then He took His disciples to the Garden of Gethsemane (literally, "Garden of the Oil-press") located on the western slope of the Mount of Olives. There Jesus prayed in agony as He contemplated the day to come. So overcome by the horror of what He was to experience in the crucifixion the following day that His sweat was "like drops of blood" (Luke 22:44) and God sent an angel from heaven to strengthen Him (Luke 22:43).
After Jesus prayed, Judas Iscariot arrived with a multitude of soldiers, high priests, Pharisees, and servants to arrest Jesus. Judas identified Jesus by the prearranged signal of a kiss, which he gave to Jesus. Trying to protect Jesus, Peter drew a sword and attacked a man named Malchus, the servant of the high priest, cutting off his ear. Jesus rebuked Peter and healed the man's ear, displaying the miraculous power of God (Luke 22:51). Nevertheless, the mob arrested Jesus and took Him to face trial, while the disciples scattered in fear for their lives.
After the trials, crucifixion, and resurrection, Jesus once again stood on the Mount of Olives. During His final post-resurrection appearance, Jesus led His disciples "out to the vicinity of Bethany, [and] he lifted up his hands and blessed them. While he was blessing them, he left them and was taken up into heaven. Then they worshiped him and returned to Jerusalem with great joy" (Luke 22:50–52). Acts 1:12 specifies that "the vicinity of Bethany" was indeed the Mount of Olives.
Immediately following Jesus' ascension, two angels told the disciples on the Mount of Olives that "this same Jesus, who has been taken from you into heaven, will come back in the same way you have seen him go into heaven" (Acts 1:11). According to the prophet Zechariah, Jesus will return not only in the same way, but to the same place. In a prophecy related to the end times, Zechariah declares, "On that day his feet will stand on the Mount of Olives, east of Jerusalem, and the Mount of Olives will be split in two from east to west, forming a great valley, with half of the mountain moving north and half moving south" (Zechariah 14:4). The very location where David wept in defeat and where Jesus was betrayed and rejected will be the place where Jesus returns in triumph over all His enemies.