We will use Matthew's account. It was late Thursday night in the last week of the life of Christ. They had been in Jerusalem where they celebrated the Feast of the Passover. After the supper and the identifying of the one who would betray Him and the instituting of the Lord's Supper, they sang a song and then left Jerusalem, probably thru the East Gate and went down across the Kidron Brook and up to the Mount of Olives.
Why did Jesus go up to the Mount of Olives? Several reasons are suggested:
Surly it was beautiful up there on the Mount of Olives. It was higher than the Temple mount and looked out not only on Jerusalem to the west but also on Bethphage and Bethany to the east.
There on the Mount of Olives Jesus warned the disciples that they would fall away because of what would happen to Him that night. One had already betrayed and the others would leave him shortly because of fear for their lives. At that time they were weak, Satan was busy, God permits even those whose hearts are right an occasional moment of weakness to keep us humble.
We must be prepared for those times of weakness. We must never be as Peter was, puffed up in our own steadfastness for it is then that we are most apt to fail. Notice Peter, as usual, talking without thinking, "Though they all run away, I will never run away." Isn't it befitting that it was Peter that would deny his Master 3 times before the night was over. "Not I Lord, I would rather die with you than deny you." What can we say, how can we escape the pitfall into which Peter fell?
Then Jesus set the Disciples around Him there on the mountain and bids them farewell. Only John recorded this dissertation.
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