Yeshua concluded His seder and farewell discourse in the upper room of a house in Jerusalem’s upper city. He went out “as was His custom to the Mount of Olives; and the disciples also followed Him.” They did not return to Bethany that night because the Torah required those keeping Passover to remain in Jerusalem on the night of their seder. In those days, many Passover pilgrims camped on the face of the Mount of Olives. It was our Master’s custom to stay at a particular spot on the Mount of Olives during the pilgrimage festivals. “Yeshua had often met there with His disciples” (John 18:2).
The Mount of Olives is a two-and-a-half-mile spur of mountainous ridge running parallel to Jerusalem’s eastern wall line, separated from the city by the deep ravine of the Kidron Valley. The Mount of Olives plays an important part in messianic prophecy. According to the prophecies of Ezekiel, the Shechinah departs and enters from Jerusalem by means of “the mountain which is east of the city.” In the future, the Messiah will appear on the Mount of Olives to rescue Jerusalem: “In that day His feet will stand on the Mount of Olives, which is in front of Jerusalem on the east” (Zechariah 14:4).
The Sages of the Mishnah called the Mount of Olives “The Mount of Anointing (Har HaMeshichah, הר המשחה).” The messianic expectation associated with the mountain explains why devout Jews of Jerusalem favor the slopes of the Mount of Olives for burial. The resurrection of the dead will start there.Today, tombs cover the much of the western face of the mountain, but in the days of the Master, trees covered the slopes.
The Master and His disciples pitched their camp in a grove of olive trees near the foot of the mount and the Kidron valley. The grove was called Gat Shamnei (גת שמני), which means “Olive Press.” An olive press probably stood within a cave in the midst of the grove, and the disciples camped in the cave.
The name of the location hints toward the meaning of the events that took place there that night. One cannot overlook the convergence of symbolism when the Mashiach (Anointed One) prays in the midst of an olive grove, in a place called the “Olive Press,” on the slopes of the hill of messianic expectation called the “Mount of Anointing.”
In the days of the Master, the owner of the grove procured olive oil from his olives by crushing them into a mash in a stone mill and then pressing them under the intense weight of a beam-press to force the oil out. The olive imagery suggests the rite of anointing whereby the title mashiach (“anointed one,” משיח) is derived. As the Master prayed that night, he came under an intense pressure that can be compared to what an olive in an olive press must feel. He said, “My soul is deeply grieved to the point of death” (Mark 14:34). Luke 22:44 relates, “And being in agony He was praying very fervently; and His sweat became like drops of blood, falling down upon the ground.”